4-(4-Methoxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-benzamide → 4-(4-Hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-benzamide

HRID 605282Notes

Reaction equation

HRID 605282 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:28]=[CH:27][C:13]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[O:15])=[CH:12][C:11]=2[NH:29][C:30]2[C:31]3[CH:39]=[CH:38][CH:37]=[N:36][C:32]=3[N:33]=[CH:34][N:35]=2)=[CH:5][CH:4]=1.C(C1C=CC2C(NC3C=C(C=CC=3SC3C=CC(OC)=CC=3)C(NC3C=CC(C)=CC=3)=O)=NC=NC=2N=1)(C)C>>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:28]=[CH:27][C:13]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[CH:18]=3)=[O:15])=[CH:12][C:11]=2[NH:29][C:30]2[C:31]3[CH:39]=[CH:38][CH:37]=[N:36][C:32]=3[N:33]=[CH:34][N:35]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 670404324-(4-Methoxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-benzamide2×HCID 670405303-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-p-tolyl-benzamide

Product 1

HCID 670402754-(4-Hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-benzamide

Procedure

The product from Example 260C was reacted according to the procedure from Example 150 substituting the product from Example 260C for the product from Example 138 to provide a residue which was purified by trituration from methanol to provide the title compound as an off white solid (33.3 mg, 90%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 11.74 (s, 1 H), 10.54 (s, 1 H), 10.01 (s, 1 H), 9.19 (s, 1 H), 9.11 (d, J=7.35 Hz, 1 H), 8.90 (s, 1 H), 8.19 (s, 1 H), 7.86-8.08 (m, 4 H), 7.60 (t, J=7.91 Hz, 1 H), 7.46 (d, J=7.72 Hz, 1 H), 7.24-7.38 (m, 2 H), 7.03 (d, J=8.46 Hz, 1 H), 6.73-6.91 (m, 2 H); MS (ESI+) m/z 534.1 (M+H)+, (ESI−) m/z 532.2 (M−H)−.

Workup

  1. customto provide a residue which
  2. customwas purified by trituration from methanol

Sources & evidence

ORD record
ord-031b0dbd1308463a8b7e651713306c78
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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