Cyclopropanecarbonyl chloride → N-(6-((4-Methoxybenzyl)oxy)imidazo[1,2-A]pyridin-2-YL)cyclopropanecarboxamide

HRID 2095835Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH2:18])[N:17]=3)[CH:14]=2)=[CH:5][CH:4]=1.[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1>CN(C)C(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH:18][C:24]([CH:21]4[CH2:23][CH2:22]4)=[O:25])[N:17]=3)[CH:14]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-[(4-methoxybenzyl)oxy]imidazo[1,2-a]pyridin-2-amine (8.5 g, 31.6 mmol) in N,N-dimethylacetamide (80 mL) was added a solution of cyclopropanecarbonyl chloride (3.43 mL, 37.9 mmol) in N,N-dimethylacetamide (20 mL) at 0° C., and the mixture was stirred at 0° C. for 3 hr. The reaction mixture was diluted with water, and the precipitate was collected by filtration and washed with water and ethyl acetate to give the title compound (8.9 g, 83%) as a gray solid.

Workup

filtrationthe precipitate was collected by filtration
washwashed with water and ethyl acetate

Sources & evidence

ORD record: ord-4fe24f0482b44aa6bd97d21643c61c29
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

Loading…