3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-(3-trifluoromethyl-phenyl)-benzamide → N-(2-Bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

HRID 605081Notes

Reaction equation

HRID 605081 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][CH:12]=[CH:11][C:10]=1[Br:15])=[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.C(C1C=CC2C(NC3C=C(C=CC=3SC3C=CC(OC)=CC=3)C(NC3C=CC=C(C(F)(F)F)C=3)=O)=NC=NC=2N=1)(C)C.NC1C=C(C=CC=1SC1C=CC(O)=CC=1)C(NC1C=CC(Br)=CC=1)=O>>[Br:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:5](=[O:6])[C:4]1[CH:16]=[CH:17][C:18]([S:19][C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)=[C:2]([NH:1][C:39]2[C:29]3[CH:34]=[CH:33][CH:32]=[N:31][C:30]=3[N:35]=[CH:36][N:37]=2)[CH:3]=1

Participants

5

Reactant 4

HCID 247576143-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-(3-trifluoromethyl-phenyl)-benzamideHCID 66808319N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 670402693-Amino-N-(4-bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-benzamideHCID 670403463-Amino-N-(2-bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide

Product 1

HCID 67040661N-(2-Bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamideYield 60%

Procedure

The product of Example 31A was reacted with the product of Example 29A using the procedure of Example 22C substituting the product of Example 3 1A 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 (58 mg, 60%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 4.48 (d, J=5.88 Hz, 2 H) 6.84 (d, J=8.46 Hz, 2 H) 6.87-7.02 (m, 1 H) 7.13-7.44 (m, 5 H) 7.58-7.64 (m, 1 H) 7.64-7.84 (m, 2 H) 7.93 (s, 1 H) 8.62 (d, J=1.84 Hz, 1 H) 8.82-9.20 (m, 3 H) 9.94 (s, 1 H) 10.30 (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-2364f559f6824ae08fb5158aeda9a812
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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