3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-p-tolyl-benzamide → N-(4-Fluoro-3-methyl-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

HRID 605284Notes

Reaction equation

HRID 605284 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:36])[C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)=[C:12]([NH:25][C:26]3[C:27]4[CH:35]=[CH:34][CH:33]=[N:32][C:28]=4[N:29]=[CH:30][N:31]=3)[CH:11]=2)=[CH:4][C:3]=1[CH3:37].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>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:36])[C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)=[C:12]([NH:25][C:26]3[C:27]4[CH:35]=[CH:34][CH:33]=[N:32][C:28]=4[N:29]=[CH:30][N:31]=3)[CH:11]=2)=[CH:4][C:3]=1[CH3:37]

Participants

3

Reactant 2

HCID 670405303-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-p-tolyl-benzamideHCID 67041022N-(4-Fluoro-3-methyl-phenyl)-4-(4-methoxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide2×

Product 1

HCID 67040239N-(4-Fluoro-3-methyl-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

Procedure

The product from Example 261A was reacted according to the procedure from Example 150 substituting the product from Example 261A 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 (30.4 mg, 82%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 10.22 (s, 1 H), 10.01 (s, 1 H), 9.20 (d, J=3.68 Hz, 1 H), 9.12 (d, J=8.82 Hz, 1 H), 8.92 (s, 1 H), 7.83-8.00 (m, 4 H), 7.64 (dd, J=7.17, 2.39 Hz, 1 H), 7.50-7.60 (m, 1 H), 7.29-7.34 (m, 2 H), 7.12 (t, J=9.19 Hz, 1 H), 7.02 (d, J=8.46 Hz, 1 H), 6.80-6.85 (m, 2 H), 2.23 (d, J=1.84 Hz, 3 H); MS (ESI+) m/z 498.1 (M+H)+, (ESI−) m/z 496.1 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-ea7d2ec2ba5843188a054daa5c4dc571
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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