3-Aminobenzamide → HCID 67040272, compound

HRID 605100Notes

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.[NH2:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=1)[C:43]([NH2:45])=[O:44]>>[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:39][C:40]3[CH:48]=[CH:47][CH:46]=[C:42]([C:43](=[O:44])[NH2:45])[CH:41]=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 16453-Aminobenzamide

HCID 86615545HCID 86615545, compound

Product 1

HCID 67040272HCID 67040272, compound

Procedure

A solution of the product from Example 43D and 3-Amino-benzamide was reacted to provide 4-(4-Benzyloxy-phenoxy)-N-(3-carbamoyl-phenyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-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 (30 mg, 56%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.35 (d, J=6.62 Hz, 6 H) 3.28 (m, 1 H) 6.78 (m, 2 H) 6.94 (m, 3 H) 7.40 (m, 2 H) 7.60 (d, J=7.72 Hz, 1 H) 7.91 (m, 3 H) 8.02 (dd, J=8.82, 2.21 Hz, 1 H) 8.17 (d, J=2.21 Hz, 1 H) 8.22 (m, 1 H) 8.91 (s, 1 H) 9.00 (d, J=8.46 Hz, 1 H) 9.48 (s, 1 H) 10.37 (s, 1 H) 11.50 (s, 1 H); MS (ESI+) m/z 535 (M+H)+.

Sources & evidence

ORD record: ord-9ae826ca6b334d8284a986d160ec88f1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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