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

HRID 1159902Notes

Reaction equation

HRID 1159902 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.Br[C:32]1[C:33](CC(C2SC=CC=2)=O)=[C:34]([CH:38]=[CH:39][C:40]=1F)[C:35](Cl)=[O:36]>>[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:35](=[O:36])[C:34]6[CH:33]=[CH:32][CH:40]=[CH:39][CH:38]=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 595114034-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-fluorophenyl)-2-pyrimidinamineHCID 86618778HCID 86618778, compound

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 in a manner analogous to Example 66, using 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-fluorophenyl)-2-pyrimidinamine and 3-bromofluoro-2-thiophenecarbonylmethylbenzoyl chloride. HRMS: calc. C28H19N6OSFBr calcd for C31H22F2N6O: 532.1823, found: 533.1921 (M+H)+ 585.0508 found 585.0515+).

Sources & evidence

ORD record
ord-6d45f1dd7de949e6bc9f02f964fde9c7
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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