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Thursday, 21 June 2018

TIPIFARNIB, типифарниб , تيبيفارنيب , 替匹法尼 ,

Tipifarnib.svgDB04960.pngChemSpider 2D Image | tipifarnib | C27H22Cl2N4O

str1
TIPIFARNIB
R-115777, NSC-702818
Categories
UNIIMAT637500A
CAS number 192185-72-1 +form
192185-68-5 (racemate)
192185-69-6 (racemic; fumarate)
192185-70-9 (racemic; diHCl)
(+)-(R)-6-[1-Amino-1-(4-chlorophenyl)-1-(1-methylimidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2(1H)-one
2(1H)-Quinolinone, 6-[(R)-amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-
Weight Average: 489.396
Chemical Formula C27H22Cl2N4O
типифарниб [Russian] [INN]
تيبيفارنيب [Arabic] [INN]
替匹法尼 [Chinese] [INN]
(R)-(+)-R115777
(R)-6-(Amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone
(R)-6-(amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methylquinolin-2(1H)-one
2 (1H))-Quinolinone,6-(amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-, 2(1H )-quinolinone
 
Title: Tipifarnib
CAS Registry Number: 192185-72-1; 192185-68-5 (unspecified stereo)
CAS Name: 6-[(R)-Amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone
Manufacturers' Codes: R-115777
Trademarks: Zarnestra (Janssen)
Molecular Formula: C27H22Cl2N4O
Molecular Weight: 489.40
Percent Composition: C 66.26%, H 4.53%, Cl 14.49%, N 11.45%, O 3.27%
Literature References: Farnesyl transferase inhibitor. Prepn: M. G. Venet et al., WO 9721701eidemUS 6037350 (1997, 2000 both to Janssen). Review of syntheses: P. R. Angibaud et al., Eur. J. Org. Chem. 2004, 479-486. Inhibition of farnesyl protein transferase and antitumor effects in vivo: D. W. End et al., Cancer Res. 61, 131 (2001). Clinical pharmacology and pharmacokinetics: J. Zujewski et al., J. Clin. Oncol. 18, 927 (2000). Accelerator mass spec determn in biological samples: R. C. Garner et al., Drug Metab. Dispos. 30, 823 (2002). Clinical evaluation in hematologic malignancies: J. Cortes et al., Blood 101, 1692 (2003). Review of clinical experience: P. Norman, Curr. Opin. Invest. Drugs 3, 313-319 (2002).
Properties: Crystals from 2-propanol, mp 234°. [a]D20 +22.86° (c = 0.98 in methanol).
Melting point: mp 234°
Optical Rotation: [a]D20 +22.86° (c = 0.98 in methanol)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Farnesyl Transferase Inhibitors.
NMR SIMULATION
PREDICTED VALUES
1H NMR: δ 3.42 (3H, s), 3.63 (3H, s), 6.57 (1H, s), 6.67 (1H, d, J = 1.7 Hz), 7.27 (1H, dd, J = 8.3, 1.5 Hz), 7.36-7.59 (8H, 7.46 (ddd, J = 8.3, 1.5, 0.5 Hz), 7.41 (ddd, J = 8.1, 8.1, 0.5 Hz), 7.39 (ddd, J = 8.1, 1.6, 1.5 Hz), 7.49 (ddd, J = 8.1, 1.7, 1.5 Hz), 7.55 (ddd, J = 8.3, 1.6, 0.5 Hz), 7.58 (d, J = 1.7 Hz)), 7.66 (1H, dd, J = 8.3, 0.5 Hz), 7.71 (1H, dd, J = 1.5, 0.5 Hz), 7.84 (1H, ddd, J = 1.7, 1.6, 0.5 Hz).

13C NMR PREDICT

str1

COSY PREDICT

HSQC PREDICT

See SYNTHESIS

 https://newdrugapprovals.org/2018/06/21/tipifarnib-%D1%82%D0%B8%D0%BF%D0%B8%D1%84%D0%B0%D1%80%D0%BD%D0%B8%D0%B1-%D8%AA%D9%8A%D8%A8%D9%8A%D9%81%D8%A7%D8%B1%D9%86%D9%8A%D8%A8-%E6%9B%BF%E5%8C%B9%E6%B3%95%E5%B0%BC/

Saturday, 2 June 2018

Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles

Graphical abstract: Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles

Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles

 Author affiliations

Abstract

An efficient synthesis of fully substituted 2,3-dihydropyrroles has been achieved in one step through the three-component reaction of amines, aromatic aldehydes and α-ketoamides. This atom-economical and catalyst-free reaction is highly stereoselective and generates underexplored heterocycles in a single step. These compounds were examined in an enzymatic assay that led to the identification of potent α-glucosidase inhibitors, thereby demonstrating the utility of this novel methodology in medicinal chemistry.




N-(4-Chlorophenyl)-2-oxopropanamide (3a) Cl H N O O 3a Using 4-chloroaniline (1.0 g, 7.8 mmol), in accordance with General Procedure A, the title compound 3a was obtained (810 mg, 52% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.73 (s, 1H), 7.60 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 2.57 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 197.1, 157.6, 135.0, 130.6, 129.5, 121.1, 24.2. HRMS (ESI-TOF) m/z calcd. for C9H7NO2Cl- [M-H]- : 196.0171, found 196.0170






Friday, 27 April 2018

Tert-butyl (N-[3-[(3S,4R)-3-amino-4-fluoro-4-(hydroxymethyl)tetrahydrofuran-3-yl]-4-fluorophenyl]acetamide)

STR1

tert-butyl (N-[3-[(3S,4R)-3-amino-4-fluoro-4-(hydroxymethyl)tetrahydrofuran-3-yl]-4-fluorophenyl]acetamide)

STR1
1H-NMR (500 MHz, DMSO-d6): 1.31 (s, 9H), 2.02 (s, 3H), 3.21 (m, 1H), 3.88 (m, 1H), 3.94 (m, 1H), 4.03 (m, 1H), 4.13 (m, 1H), 4.74 (m, 1H), 5.07 (m, 1H), 7.08 (m, 1H), 7.43 (bs, 1H), 7.63 (m, 1H), 7.67 (m, 1H), 10.03 (s, 1H) .
STR2
13C-NMR (125 MHz, DMSO-d6): 24.3, 28.5, 60.8, 65.1, 72.6, 78.1, 78.9, 105.8, 116.4, 119.7, 120.8, 127.2, 136.2, 155.2, 156.4, 168.7.
str3
19F-NMR (470.6 MHz, DMSO-d6): -164.77, -117.26.

str4 str5
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00069

Tuesday, 17 April 2018

Cookson’s Dione

Cyclopentadienebenzoquinone.png
Chemical Names:Cyclopentadienebenzoquinone; 1200-89-1; 1,4,4a,8a-Tetrahydro-1,4-methanonaphthalene-5,8-dione; 1,4-Methanonaphthalene-5,8-dione, 1,4,4a,8a-tetrahydro-; NSC 25329; 1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione
Molecular Formula:C11H10O2
Molecular Weight:174.199 g/mol
str3
1H NMR (CDCl3, 400 MHz) δ = 1.41 (dt, J = 8.8, 1.5 Hz, 1H), 1.52 (dt, J = 8.8, 1.8 Hz, 1H), 3.20 (dd, J = 2.5, 1.5 Hz, 2H), 3.52 (m, 2H), 6.04 (t, J = 1.9 Hz, 2H), 6.54 (s, 2H).
13C NMR (CDCl3, 100 MHz) δ = 48.4 (2 × CH), 48.8 (CH), 48.9 (2 × CH), 135.4 (2 × CH), 142.1 (2 × CH), 199.5 (2 × CO)
O=C3C=CC(=O)C2C3C1C=CC2C1
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00037
Abstract ImageWe report the use of a simple rotary evaporator as a semi-continuous UV photochemical reactor. By generation of a thin film from the rotation of a flask, better light penetration is achieved, and in this work we used high-power Hg lamps to enable the direct irradiation of molecules with UV light. The intramolecular [2 + 2] photocycloaddition of Cookson’s dione and the intermolecular [2 + 2] photocycloaddition of maleimide with 1-hexyne were used as test reactions to examine the effectiveness of this reactor. High productivities, equivalent to 210 g h–1, were obtained for the simple intramolecular reaction, demonstrating the scalability of the reactor. The effects of flask size, reaction mixture volume, and use of borosilicate or quartz glassware were also investigated.
 
 

Cookson’s Dione

COOKSON'S DIONE
CAS No.: 2958-72-7
1H NMR (CDCl3, 300 MHz) δ = 1.86 (d, J = 11.3, 1H), 2.02 (d, J = 11.3, 1H), 2.68 (m, 2H), 2.79 (m, 2H), 2.90 (m, 2H), 3.15 (m, 2H).
 
Figure
 
References 1. Clark, C. A.; Lee, D. S.; Pickering, S. J.; Poliakoff, M.; George, M. W. Org. Process Res. Dev. 2016, 20, 1792-1798. 2. Elliott, L. D.; Knowles, J. P.; Koovits, P. J.; Maskill, K. G.; Ralph, M. J.; Lejeune, G.; Edwards, L. J.; Robinson, R. I.; Clemens, I. R.; Cox, B.; Pascoe, D. D.; Koch, G.; Eberle, M.; Berry, M. B.; Booker-Milburn, K. I. Chem. Eur. J. 2014, 20, 15226-15232. 3. Marchand, A. P.; Allen, R. W. J. Org. Chem. 1974, 39, 1596-1596. 4. Elliott, L. D.; Berry, M.; Harji, B.; Klauber, D.; Leonard, J.; Booker-Milburn, K. I. Org. Process Res. Dev. 2016, 20, 1806-1811. 5. Hook, B. D. A.; Dohle, W.; Hirst, P. R.; Pickworth, M.; Berry, M. B.; Booker-Milburn, K. I. J Org Chem 2005, 70, 7558-7564.

ORGANIC SPECTROSCOPY INTERNATIONAL: Cookson's Dione

https://orgspectroscopyint.blogspot.com/search/label/Cookson’s%20Dione
 
Oct 3, 2016 - Cookson's Dione 125 W Batch Reaction A solution of Diels Alder adduct 3[3] (2.61 g, 15 mmol) in degassed EtOAc (150 ml) was irradiated with a pre-warmed 125 W medium pressure mercury lamp in a 150 ml batch reactor equipped with a. Pyrex immersion well for 15 min. The solvent was removed in ..
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Saturday, 31 March 2018

4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane

Image result for 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane


http://orgsyn.org/demo.aspx?prep=v94p0234




 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane (1) has the following physical and spectroscopic properties: Rf = 0.47 (3:97, ethyl acetate:pentane), the checkers report the following values for 1: Rf = 0.09 (3:97 ethyl acetate:pentane); R= 0.52 (10% EtOAc in hexanes); Merck silica gel 60 F254 plate; mp 38-39 °C; 

1H NMR pdf(CDCl3, 400 MHz) δ: 1.18 (t, = 8.4 Hz, 2H), 1.26 (s, 12H), 2.79 (t, J = 8.0 Hz, 2H), 7.16-7.22 (m, 1H), 7.23-7.32 (m, 4H); 

13C NMR pdf(CDCl3, 151 MHz) d: 25.0, 30.1, 83.2, 125.6, 128.1, 128.3, 144.6 [N.B. the carbon attached to boron was not observed due to quadrupolar relaxation]; 

HRMS (ESI+) calculated for C14H22BO2+ = 233.1707, mass found = 233.1710; 

IR (film): 3026, 2978, 2929, 1372, 1318, 1139, 848, 755, 703 cm-1

Anal. calcd for C14H21BO2: C, 72.44; H, 9.12. Found: C, 72.18; H, 9.28. 








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Tuesday, 27 March 2018

BRUSH UP YOUR NMR, 4-(3,5-Dichloropyridin-4-yl)morpholine

str1
3,5-Dichloro-4-morpholinopyridine
 
 5 as a light-orange solid.
 
1H NMR (CDCl3, 400 MHz): δ = 8.35 (2H, s), 3.84 (4H, m), 3.37 (4H, m);
 
13C NMR (CDCl3, 101 MHz): δ = 150.8, 149.3, 128.4, 67.4, 50.4;
 
HRMS–ESI+m/z [M + H]+ calcd for C9H11Cl2N2O+: 233.02429; found: 233.02446.
 
 
 
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00009
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Clc2cncc(Cl)c2N1CCOCC1

Saturday, 24 March 2018

METHYL 2-(ACETYLTHIO)ACETATE

ChemSpider 2D Image | Methyl 2-(methylthio)acetate | C4H8O2S

Methyl 2-(methylthio)acetate

  • Molecular FormulaC4H8O2S
  • Average mass120.170 Da
  • 16630-66-3
  • S-Methylthioglycolate

DOI: 10.1021/acs.oprd.7b00378
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