N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine → N-(4-Bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

HRID 605084Notes

Reaction equation

HRID 605084 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[S:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)=[O:6].C([C:29]1[C:30]([N:35]=[CH:36][N:37]([CH3:39])C)=[N:31][CH:32]=[CH:33][CH:34]=1)#N.NC1C=C(C=CC=1SC1C=CC(O)=CC=1)C(NC1C=CC(Br)=CC=1)=O>>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][NH:7][C:5](=[O:6])[C:4]2[CH:16]=[CH:17][C:18]([S:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[C:2]([NH:1][C:39]3[C:29]4[CH:34]=[CH:33][CH:32]=[N:31][C:30]=4[N:35]=[CH:36][N:37]=3)[CH:3]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 66808319N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 670402413-Amino-N-(4-bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide2×HCID 670402693-Amino-N-(4-bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide

Product 1

HCID 67040440N-(4-Bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamideYield 26%

Procedure

The product of Example 33A was reacted with the product of Example 29A using the procedure of Example 22C substituting the product of Example 33A for the product of Example 22B and substituting the product of Example 29A for the product of Example 8E to provide the crude title compound which was purified by column chromatography on silica gel using methanol/dichloromethane as eluent to provide the title product (26 mg, 26%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 4.41 (d, J=5.88 Hz, 2 H) 6.76-6.96 (m, 1 H) 6.83 (d, J=8.46 Hz, 2 H) 7.20-7.33 (m, 4 H) 7.51 (d, J=8.46 Hz, 2 H) 7.58-7.80 (m, 2 H) 7.82-7.97 (m, 1 H) 8.52-8.69 (m, 1 H) 8.86-9.18 (m, 3 H) 9.94 (s, 1 H) 10.28 (s, 1 H); MS (ESI+) m/z 558/560 (M+H)+.

Workup

  1. customto provide the crude title compound which
  2. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-26fe5a83dacd4a8b823f07e551fa2485
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…