4-Aminopyridine → HCID 67040722, compound

HRID 605102Notes

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.[N:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=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:45][C:42]3[CH:43]=[CH:44][N:39]=[CH:40][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 17274-Aminopyridine

HCID 86615545HCID 86615545, compound

Product 1

HCID 67040722HCID 67040722, compound

Procedure

A solution of the product from Example 43D and Pyridin-4-ylamine was reacted to provide 4-(4-Benzyloxy-phenoxy)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-N-pyridin-4-yl-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, 61%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.62 Hz, 6 H) 3.27 (m, 1 H) 6.78 (m, 2 H) 6.94 (m, 3 H) 7.81 (d, J=8.46 Hz, 1 H) 8.01 (dd, J=8.64, 2.02 Hz, 1 H) 8.22 (m, 3 H) 8.72 (d, J=6.99 Hz, 2 H) 8.83 (s, 1 H) 8.96 (d, J=8.46 Hz, 1 H) 9.50 (s, 1 H) 11.10 (s, 1 H) 11.35 (s, 1 H); MS (ESI+) m/z 493 (M+H)+.

Sources & evidence

ORD record: ord-6f000991377741848d40de8fdb3b9a98
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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