1-methyl-1H-Imidazole-5-carbonyl chloride → N-(3-{3-[2-(1,2,3,4-tetrahydro-7-isoquinolinylamino)-4-pyrimidinyl]-pyrazolo[1,5-a]pyridin-2-yl}phenyl)benzamide

HRID 1159907Notes

Reaction equation

HRID 1159907 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26](F)[CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CN1[C:36]([C:37](Cl)=[O:38])=[CH:35]N=C1>>[CH2:15]1[C:26]2[C:27](=[CH:28][CH:29]=[C:24]([NH:23][C:19]3[N:18]=[C:17]([C:16]4[C:8]([C:4]5[CH:3]=[C:2]([NH:1][C:37](=[O:38])[C:36]6[CH:35]=[CH:6][CH:7]=[CH:2][CH:3]=6)[CH:7]=[CH:6][CH:5]=5)=[N:9][N:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=45)[CH:22]=[CH:21][N:20]=3)[CH:25]=2)[CH2:12][CH2:11][NH:10]1

Participants

3

Reactant 2

HCID 27765541-methyl-1H-Imidazole-5-carbonyl chlorideHCID 595114034-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-fluorophenyl)-2-pyrimidinamine

Product 1

HCID 59513880N-(3-{3-[2-(1,2,3,4-tetrahydro-7-isoquinolinylamino)-4-pyrimidinyl]-pyrazolo[1,5-a]pyridin-2-yl}phenyl)benzamide

Procedure

The title compound was prepared from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-fluorophenyl)-2-pyrimidinamine and 1-methyl-1H-imidazole-5-carbonyl chloride in a manner analogous to Example 66. 1H NMR (400 MHz, DMSO-d6): δ 10.14 (s, 1H), 9.80 (s, 1H), 8.84 (d, 1H), 8.50 (d, 1H), 8.30 (d, 1H), 8.04 (s, 1H), 7.87-7.76 (m, 4H), 7.52-7.41 (m, 3H), 7.29-7.22 (m, 2H), 7.13 (m, 1H), 6.72 (m, 1H), 6.57 (d, 1H), 3.83 (s, 3H); HRMS: calc. C28H22N8OF (M+H)+ 505.1901 found 505.1903.

Sources & evidence

ORD record
ord-e213eab69f604df0920df9e197d6deaa
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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