Entinostat

Entinostat

Also known as: ms-275, 209783-80-2, SNDX-275, MS 275, MS-27-275, SNDX 275, NSC-706995

Molecular Formula: C21H20N4O3

Molecular Weight: 376.4085 g/mol

pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate

N-(2-aminophenyl)-4-[N-(pyridine-3-yl)-methoxycarbonyl-aminomethyl]- benzamide

CAS  209783-80-2

209784-80-5 (HCl)

Bayer Schering Pharma Aktiengesellschaft

Pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate

SYN........http://newdrugapprovals.org/2015/01/09/entinostat/

http://www.google.co.in/patents/EP0974576A2?cl=en

Example 6

Synthesis of N-(2-aminophenyl)-4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzamide (an example in which after activation with N,N’-carbonyldiimidazole, an acid was added to carry out reaction)

• [0082]
  7.78 g (48 mmole) of N,N’-carbonyldiimidazole were added to a 1,3-dimethyl-2-imidazolidinone (50 g) suspension including 11.45 g (40 mmole) of 4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzoic acid. After stirring at room temperature for 2 hours, 17.30 g (0.16 mole) of 1,2-phenylenediamine were added to the solution. After cooling to 2°C, 9.60 g (0.1 mole) of methanesulfonic acid were added dropwise. After stirring for 2 hours, water was added, and the deposited solid was collected by filtration. Purification was then carried out through silica gel column chromatography to obtain 10.83 g (yield: 72%) of N-(2-aminophenyl)-4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzamide.
  Reaction selectivity based on the result in HPLC
  

  	Retention Time/min.	Area %
  Benzoylimidazole as Active Intermediate	4.3	0.00
  Monoacylated Phenylenediamine	4.7	98.91
  Diacylated Phenylenediamine	11.7	1.09

  Analysis data of the product
  mp. 159-160°C
• 
     1H NMR (270MHz, DMSO-d6) δ ppm: 4.28 (2H, d, J=5.9Hz), 4.86 (2H, s), 5.10 (2H, s), 6.60 (1H, t, J=7.3Hz), 6.78 (1H, d, J=7Hz), 6.97 (1H, t, J=7Hz), 7.17 (1H, d, J=8Hz), 7.3-7.5 (3H, m), 7.78 (1H, d, J=8Hz), 7.93 (2H, d, J=8Hz), 8.53 (1H, d, J=3.7Hz), 8.59 (1H, s), 9.61 (1H, s).
     
• IR (KBr) cm-1: 3295, 1648, 1541, 1508, 1457, 1309, 1183, 742

SYN........http://newdrugapprovals.org/2015/01/09/entinostat/



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