Ammonia → {1-[4-(7-Carbamoyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 872313Notes

Reaction equation

HRID 872313 reaction equation
CO[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:13]=[C:7]2[CH:6]=1)=[O:4].[NH3:38]>CO>[C:28]([O:27][C:25](=[O:26])[NH:24][C:20]1([C:17]2[CH:18]=[CH:19][C:14]([C:12]3[N:13]=[C:7]4[CH:6]=[C:5]([C:3](=[O:4])[NH2:38])[CH:10]=[CH:9][N:8]4[C:11]=3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:15][CH:16]=2)[CH2:21][CH2:22][CH2:23]1)([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 666656142-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester

Product 1

HCID 66665681{1-[4-(7-Carbamoyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (150 mg) and a solution of ammonia in methanol (7M, 2.15 mL) was heated at 130° C. for 90 minutes under microwave irradiation. On cooling, the reaction mixture was concentrated in vacuo. Purification was achieved by chromatography on silica gel to give the title compound.

Workup

  1. temperatureOn cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customPurification

Sources & evidence

ORD record
ord-5f49b9f948ce4e9f877df13b98dbab0f
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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