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

HRID 605177Notes

Reaction equation

HRID 605177 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:15]=[C:16]([CH:28]=[CH:29][C:30]=3[S:31][C:32]3[CH:37]=[CH:36][C:35]([O:38]C)=[CH:34][CH:33]=3)[C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26]C)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:40]=1)([CH3:3])[CH3:2].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:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][C:17](=[O:18])[C:16]1[CH:28]=[CH:29][C:30]([S:31][C:32]2[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=2)=[C:14]([NH:13][C:12]2[C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[N:40][C:8]=3[N:9]=[CH:10][N:11]=2)[CH:15]=1

Participants

3

Reactant 2

HCID 670405303-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-p-tolyl-benzamideHCID 670407233-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-N-(2-methoxy-phenyl)-4-(4-methoxy-phenylsulfanyl)-benzamide2×

Product 1

HCID 67040263N-(2-Hydroxy-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzamideYield 55%

Procedure

The product from Example 143 was reacted according to the procedure from Example 150 substituting the product from Example 143 for the product from Example 138 to provide a residue which was purified by trituration with methanol and diethyl ether to provide the title compound (26 mg, 55%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.37 (d, J=6.99 Hz, 6H), 3.21-3.43 (m, 1H), 6.83 (s, 1H), 6.84 (d, J=8.82 Hz, 2H), 6.92 (d, J=8.09 Hz, 1H), 7.02 (d, J=8.09 Hz, 2H), 7.32 (d, J=8.46 Hz, 2H), 7.63 (d, J=8.09 Hz, 1H), 7.93 (dd, J=8.46, 1.84 Hz, 1H), 7.99 (s, 1H), 8.94 (s, 1H), 9.08 (d, J=8.46 Hz, 1H), 9.51 (s, 1H), 9.74 (s, 1H), 10.02 (s, 1H); MS (APCI) m/z 524 (M+H)+.

Workup

  1. customto provide a residue which
  2. customwas purified by trituration with methanol and diethyl ether

Sources & evidence

ORD record
ord-06c141dae09641c6a5894f115c67bf60
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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