Hydrochloric Acid → 1-(3-{3-[4-(1-aminocyclobutyl)phenyl]-2-(2-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl}phenyl)-N,N-dimethylpiperidine-4-carboxamide HCl salt

HRID 1852916Notes

Reaction equation

HRID 1852916 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[N:33]([C:34]3[CH:39]=[CH:38][C:37]([C:40]4([NH:44]C(=O)OC(C)(C)C)[CH2:43][CH2:42][CH2:41]4)=[CH:36][CH:35]=3)[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N:22]5[CH2:27][CH2:26][CH:25]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH2:24][CH2:23]5)[CH:17]=4)=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.CO.[ClH:54]>C(OCC)(=O)C>[ClH:54].[NH2:44][C:40]1([C:37]2[CH:36]=[CH:35][C:34]([N:33]3[C:11]4=[N:12][C:13]([C:16]5[CH:17]=[C:18]([N:22]6[CH2:27][CH2:26][CH:25]([C:28]([N:29]([CH3:31])[CH3:30])=[O:32])[CH2:24][CH2:23]6)[CH:19]=[CH:20][CH:21]=5)=[CH:14][CH:15]=[C:10]4[N:9]=[C:8]3[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=3)=[CH:39][CH:38]=2)[CH2:41][CH2:42][CH2:43]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 71142509tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[4-(dimethylcarbamoyl)piperidin-1-yl]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate

Product 1

HCID 711385481-(3-{3-[4-(1-aminocyclobutyl)phenyl]-2-(2-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl}phenyl)-N,N-dimethylpiperidine-4-carboxamide HCl saltYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

tert-Butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[4-(dimethylcarbamoyl)piperidin-1-yl]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate (3.4 g, 4.9 mmol) was deprotected with methanol (15 mL) and 4M HCl in ethyl acetate (15 mL) for 18 h at rt. The mixture was solidified with ethyl acetate and collected with filtration to give the titled compound (2.9 g, 100%) as a white solid.

Workup

  1. filtrationcollected with filtration

Sources & evidence

ORD record
ord-03fb08cfc94b465eb89b329bca45dd1c
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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