N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine → {4-[4-(3-Bromo-phenylcarbamoyl)-2-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenyl}-carbamic acid tert-butyl ester

HRID 605115Notes

Reaction equation

HRID 605115 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[CH:17][C:16]=2[NH2:31])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([C:35]1[C:36]([N:42]=[CH:43][N:44]([CH3:46])C)=[N:37][C:38]([CH3:41])=[CH:39][CH:40]=1)#N>>[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[CH:17][C:16]=2[NH:31][C:46]2[C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[N:37][C:36]=3[N:42]=[CH:43][N:44]=2)=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 67040779{4-[2-Amino-4-(3-bromo-phenylcarbamoyl)-phenylsulfanyl]-phenyl}-carbamic acid tert-butyl ester2×

Product 1

HCID 67040669{4-[4-(3-Bromo-phenylcarbamoyl)-2-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenyl}-carbamic acid tert-butyl esterYield 21%

Procedure

The product of Example 64A was reacted with the product of Example 9B using the procedure of Example 13D substituting the product of Example 64A for the product of Example 13C 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 compound (27 mg, 21%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.48 (s, 9 H) 2.69 (s, 3 H) 7.00 (d, J=8.09 Hz, 1 H) 7.34 (m, 4 H) 7.54 (m, 3 H) 7.72 (m, 1 H) 7.81 (d, J=8.09 Hz, 1 H) 8.01 (s, 1 H) 8.07 (s, 1 H) 8.60 (s, 1 H) 8.82 (d, J=8.46 Hz, 1 H) 9.60 (s, 1 H) 10.22 (s, 1 H) 10.34 (s, 1 H); MS (ESI+) m/z 657, 659 (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-a1ed13b5fd4e40f0af25570e4251bd99
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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