Hydrochloric Acid → 2,6-Difluoro-N-{3-[3-(2-{[4-(methyloxy)-3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}benzamide

HRID 1160014Notes

Reaction equation

HRID 1160014 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][C:37]=1[N:43]1[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]1.Cl>C(O)(C)C>[F:32][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([F:31])[C:25]=1[C:24]([NH:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:9]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:42][C:39]4[CH:40]=[CH:41][C:36]([O:35][CH3:34])=[C:37]([N:43]5[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]5)[CH:38]=4)[N:7]=3)=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH:18]=1)=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)anilineHCID 59513803N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

Product 1

HCID 116646122,6-Difluoro-N-{3-[3-(2-{[4-(methyloxy)-3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}benzamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (which may be prepared according to a procedure similar to Example 11, Step C) and [4-(methyloxy)-3-(4-methyl-1-piperazinyl)phenyl]amine are heated in isopropanol with catalytic conc. HCl at approximately 85° C. to afford the product. ES-LCMS m/z 647 (M+H).

Workup

  1. custommay be prepared
  2. customto afford the product

Sources & evidence

ORD record
ord-88a4c79c11604d979379719db56bc766
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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