P-Anisidine → HCID 67040693, compound

HRID 605109Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:38]=[CH:37][C:12]([O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][C:15]=2[NH:23][C:24]2[C:25]3[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[N:30][C:26]=3[N:27]=[CH:28][N:29]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=1>>[CH2:1]([O:8][C:9]1[CH:38]=[CH:37][C:12]([O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH:47][C:44]3[CH:45]=[CH:46][C:41]([O:40][CH3:39])=[CH:42][CH:43]=3)=[O:19])=[CH:16][C:15]=2[NH:23][C:24]2[C:25]3[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[N:30][C:26]=3[N:27]=[CH:28][N:29]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7732P-Anisidine

HCID 86615545HCID 86615545, compound

Product 1

HCID 67040693HCID 67040693, compound

Procedure

A solution of the product from Example 43D and 4-Methoxy-phenylamine was reacted to provide 4-(4-Benzyloxy-phenoxy)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-N-(4-methoxy-phenyl)-benzamide using the procedure from Example 43E. The material was then deprotected using the procedure from Example 43F to provide the crude title compound which was purified by HPLC with TFA to provide the title compound as a trifluoroacetic acid salt (27 mg, 52%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6 H) 3.28 (m, 1 H) 3.74 (s, 3 H) 6.77 (m, 2 H) 6.92 (m, 5 H) 7.64 (m, 2 H) 7.87 (d, J=8.82 Hz, 1 H) 7.96 (dd, J=8.64, 2.02 Hz, 1 H) 8.12 (d, J=2.21 Hz, 1 H) 8.89 (s, 1 H) 8.99 (d, J=8.46 Hz, 1 H) 9.46 (s, 1 H) 10.12 (s, 1 H) 11.41 (s, 1 H); MS (ESI+) m/z 522 (M+H)+.

Sources & evidence

ORD record: ord-07a757d300974f8e87f1c2166453a666
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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