3-Aminopyridine → HCID 67040304, compound

HRID 605101Notes

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][CH:42]=[C:41]([NH2:45])[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:41]3[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=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 100093-Aminopyridine

HCID 86615545HCID 86615545, compound

Product 1

HCID 67040304HCID 67040304, compound

Procedure

A solution of the product from Example 43D and Pyridin-3-ylamine was reacted to provide 4-(4-Benzyloxy-phenoxy)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-N-pyridin-3-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 (23 mg, 47%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.35 (d, J=6.99 Hz, 6 H) 3.29 (m, 1 H) 6.78 (m, 2 H) 6.95 (m, 3 H) 7.54 (dd, J=8.27, 4.96 Hz, 1 H) 7.90 (d, J=8.82 Hz, 1 H) 8.02 (dd, J=8.82, 2.21 Hz, 1 H) 8.16 (d, J=2.21 Hz, 1 H) 8.29 (m, 1 H) 8.39 (dd, J=4.78, 1.47 Hz, 1 H) 8.94 (s, 1 H) 9.04 (m, 2 H) 9.48 (s, 1 H) 10.59 (s, 1 H) 11.59 (s, 1 H); MS (ESI+) m/z 493 (M+H)+.

Sources & evidence

ORD record: ord-ffce4589daa24f59b2f41441a09ef49e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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