Methylamine → N-(1-{2,6-dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide

HRID 2201891Notes

Reaction equation

Br[CH2:2][C:3]1[CH:25]=[C:24]([Cl:26])[C:6]([C:7]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[C:12]=3[CH:11]=[CH:10]2)=[O:8])=[C:5]([Cl:27])[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:34][NH2:35]>C(#N)C>[Cl:26][C:24]1[CH:25]=[C:3]([CH2:2][NH:35][CH3:34])[CH:4]=[C:5]([Cl:27])[C:6]=1[C:7]([N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[C:12]=2[CH:11]=[CH:10]1)=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-{1-[4-(bromomethyl)-2,6-dichlorobenzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide (50 mg, 0.107 mmol) in acetonitrile was treated with cesium carbonate (69.74 mg, 0.2140 mmol) and stirred for about 15 minutes. The mixture was cooled to 0° C. followed by the portion wise addition of methyl amine (10.68 mg, 0.16 mmol). The reaction mixture was then stirred at room temperature for about 20 minutes and concentrated under vacuum, followed by addition of ice cold water to give N-(1-{2,6-dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide (27.5 mg) as white solid.

Workup

stirringThe reaction mixture was then stirred at room temperature for about 20 minutes
concentrationconcentrated under vacuum
additionfollowed by addition of ice cold water

Sources & evidence

ORD record: ord-10a0999e5cb641fe80c707cd445990e8
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09364466B2

Reaction notes

Loading…