N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine → N-(3-Bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

HRID 605075Notes

Reaction equation

HRID 605075 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[S:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1)=[O:6].C([C:28]1[C:29]([N:35]=[CH:36][N:37]([CH3:39])C)=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=1)#N.NC1C=C(C=CC=1SC1C=CC(O)=CC=1)C(NC1C=CC(Br)=CC=1)=O>>[Br:14][C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:15]=[CH:16][C:17]([S:18][C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[C:2]([NH:1][C:39]3[C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[N:30][C:29]=4[N:35]=[CH:36][N:37]=3)[CH:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 670402693-Amino-N-(4-bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-benzamideHCID 670409183-Amino-N-(3-bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide2×

Product 1

HCID 67040299N-(3-Bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzamideYield 47%

Procedure

The product of Example 26A was reacted with the product of Example 9B using the procedure of Example 22C substituting the product of Example 26A for the product of Example 22B and substituting the product of Example 9B 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 (22 mg, 47%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.68 (s, 3 H) 6.81-6.89 (m, 2 H) 6.89-7.01 (m, 1 H) 7.22-7.38 (m, 4 H) 7.49-7.64 (m, 1 H) 7.67-7.89 (m, 2 H) 7.92-8.03 (m, 1 H) 8.04-8.17 (m, 1 H) 8.58 (s, 1 H) 8.70-8.91 (m, 1 H) 9.96 (s, 1 H) 10.20 (s, 1 H) 10.31 (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-7b1883574e2b45c3a5ab852ed3589fce
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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