4-((3,4-Dimethoxyphenylamino)methyl)-N-(2-amino-5-cyanophenyl)benzamide

 


http://www.google.com/patents/US7868205

 Example 55

4-((3,4-Dimethoxyphenylamino)methyl)-N-(2-amino-5-cyanophenyl)benzamide (199)

Step 1: 4-((3,4-Dimethoxyphenylamino)methyl)-N-(2-amino-5-cyanophenyl)benzamide (199) Following the same procedure as described in Example 27, step 2 (scheme 20), the title compound 199 was obtained in 16% yield.  


¹H NMR: (DMSO)
δ (ppm): 9.56 (bs, 1H),
7.89 (d, J=8.0 Hz, 2H),
7.52 (bs, 1H),
7.45 (d, J=8.4 Hz, 2H),
6.77 (d, J=8.4 Hz, 1H),
6.63 (d, J=8.4 Hz, 1H),
6.30 (d, J=2.4 Hz, 1H),
5.99-5.95 (m, 2H),
5.74 (bs, 1H),
4.92 (bs, 2H),
3.64 (s, 3H),
3.32 (s, 3H).


MS: (calc); 402.5 (obt.) 403.4 (MH)⁺.

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Plumbagin analogs-synthesis, characterization, and antitubercular activity

Compound a

This was synthesized using above scheme. R _f 0.44 (Silica Gel G, n-hexane: EtOAc, 10:2); 

IR (cm ^-1 ) 3067 (Aromatic C-H), 2985 (Aliphatic-CH₂ ), 1678 (Aryl C = C), 1631 (C = O), 1452 (Aromatic ring stretch); 
nmr
(400 MHz, DMSO-d6), dH ppm: 2.469 (1H, s), 3.025-3.006 (4H, q, J = 7.6 Hz), 1.258-1.240 (3H, t, J = 7 Hz), 6.998 (1H, m), 7.126 (1H, m), 7.254 (1H, m), 7.468 (1H, m), 7.536 (1H, m), 7.552 (1H, m), 8.076 (1H, m), 7.969 (1H, s), 7.900 (1H, s), 8.605 (1H, s); m ⁄ z 507.13(M+).

http://www.japtr.org/article.asp?issn=2231-4040;year=2014;volume=5;issue=1;spage=28;epage=32;aulast=Nayak

Phylligenin

 Phylligenin

Phenol,4-[(1R,3aS,4S,6aS)-4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxy-;
Phenol,4-[4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxy-,[1R-(1a,3aa,4b,6aa)]-;
1H,3H-Furo[3,4-c]furan,phenol deriv.;
(-)-Phylligenin;
Phylligenin;
Phyllygenin;
Symplocosigenolmonomethyl ether

(-)-Phylligenin; 
1H,3H-Furo[3,4-: 23397-47-9. 名 称: Phenol,4-[(1R,3aS,4S,6aS)-4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxy

C21H24O6
372.00



IR

(KBr) 3450, 1600, 1585, 1510, 1455, 1260



MASS
EIMS m/z (rel. int.) 372 [M]+ (19), 355 (42), 337 (5), 325 (8), 249 (100), 235 (82), 219 (44), 205 (48), 189 (37), 175 (27), 151 (59), 137 (72)










1H NMR

(250 MHz, CDCl3) δ: 6.81-6.91 (6H, m, Ar-H), 5.64 (1H, s, OH), 4.86 (1H, d, J = 5.2 Hz, H-7), 4.42 (1H, d, J = 7.2 Hz, H-7'), 4.13 (1H, d, J = 9.4 Hz, H-9'a), 3.81 (6H, 2 × OCH3), 3.79 (3H, OCH3), 3.58-4.37 (3H, m, H-9, H-9'), 3.21-3.49 (2H, m, H-8', H-9), 2.85 (1H, m, H-8) 13 C NMR (63 MHz, CDCl3) δ: 149.2 (C-3), 148.3 (C-4), 147.1 (C-3'), 145.7 (C-4'), 133.4 (C-1'), 131.3 (C-1), 119.6 (C-6'), 118.1 (C-6), 114.6 (C-5'), 111.3 (C-5), 109.2 (C-2'), 108.9 (C-2),  88.1 (C-7'), 82.4 (C-7), 71.4 (C-9'), 70.1 (C-9), 56.3 (3-OCH3, 4-OCH3, 3'-OCH3), 54.9 (C-8'), 50.5 (C-8) INSTITUTE OF CHEMISTRY UNIVERSITY OF SINDH JAMSHORO INSTITUTE OF CHEMISTRY,  UNIVERSITY OF SINDH,  JAMSHORO, sindh pakistan

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Chorismic Acid

Chorismic Acid

CAS Registry Number: 617-12-9

CAS Name: (3R-trans)-3-[(1-Carboxyethenyl)oxy]-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid

Additional Names: 3-enolpyruvic ether of trans-3,4-dihydroxycyclohexa-1,5-diene carboxylic acid; a-(5-carboxy-1,2-dihydro-2-hydroxyphenoxy)acrylic acid

Molecular Formula: C10H10O6

Molecular Weight: 226.18

Percent Composition: C 53.10%, H 4.46%, O 42.44%

1H NMR

13 CNMR

Literature References: The first branch point intermediate in the biosynthesis of aromatic amino acids via the shikimate pathway in bacteria, fungi, and higher plants; naturally occurring as the (-)-form. Its existence was predicted, then discovered during development of a mutant of A. aerogenes: M. I. Gibson et al., Nature 195, 1173 (1962); M. I. Gibson, F. Gibson, Biochim. Biophys. Acta 65, 160 (1962). NMR and preliminary structure study: F. Gibson, M. Jackman, Nature 198, 388 (1963). Isoln and metabolism study: M. Gibson, F. Gibson, Biochem. J. 90, 248 (1964). Prepn and characterization of the barium salt: F. Gibson, ibid. 256. Structure, relative and abs config, prepn of the monohydrate: J. M. Edwards, L. M. Jackman, Aust. J. Chem. 18, 1227 (1965). Total synthesis of racemic chorismic acid: D. A. McGowan, G. A. Berchtold, J. Am. Chem. Soc. 104, 1153 (1982); B. Ganem et al., ibid. 6787; improved synthesis: G. A. Berchtold et al., ibid. 105, 6265 (1983); short formal synthesis: G. H. Posner et al., J. Org. Chem. 52, 4836 (1987). Total synthesis of (-)-form: J. L. Pawlak, G. A. Berchtold, ibid. 1765. Potential use in development of herbicides: S. Stinson, Chem. Eng. News 60, 31 (Dec. 6, 1982). Reviews of chorismic acid in biosynthesis of aromatic amino acids: F. Gibson, J. Pittard, Bacteriol. Rev. 32, 465-492 (1968); R. J. Ife et al., J. Chem. Soc. Perkin Trans. 1 1976, 1776-1783; U. Weiss, J. M. Edwards, The Biosynthesis of Organic Compounds (Wiley, New York, 1980) pp 134-143. See also shikimic acid.

Properties: Crystals may be obtained but show marked tendency toward solvent retention, mp 105-108° (dec). [a]D21 -274° (c = 0.16 in water).

Melting point: mp 105-108° (dec)

Optical Rotation: [a]D21 -274° (c = 0.16 in water)

 

Derivative Type: Barium salt trihydrate

Molecular Formula: C10H8BaO6.3H2O

Molecular Weight: 415.54

Percent Composition: C 28.90%, H 3.40%, Ba 33.05%, O 34.65%

Properties: Unstable. uv max (aq soln): 272 nm (e 2700).

Absorption maximum: uv max (aq soln): 272 nm (e 2700)

 

Derivative Type: Monohydrate

Properties: Colorless crystals from ethyl acetate + light petroleum, mp 148-149° (dec); from ether + light petroleum, mp 112° (dec); from ethyl acetate + carbon tetrachloride, mp 115° (dec). [a]255890 -295.5° (c = 0.2 in water). uv max (water): 275 nm (e2630).

Melting point: mp 148-149° (dec); mp 112° (dec); mp 115° (dec)

Optical Rotation: [a]255890 -295.5° (c = 0.2 in water)

Absorption maximum: uv max (water): 275 nm (e 2630)

 

Derivative Type: (±)-Form

Properties: Crystals from ethyl acetate/hexane, mp 139.4-141° (dec).

Melting point: mp 139.4-141° (dec)