Ammonia methanol → 7-[2-(6-Cyanopyridin-3-yl)ethyl]-4-(2-fluoro-4-methoxyphenyl)quinoline-2-carboxamide

HRID 922812Notes

Reaction equation

[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=4[F:33])=[CH:16][C:17]([C:21]([O:23]C)=O)=[N:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[NH3:34].CO>CO>[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=4[F:33])=[CH:16][C:17]([C:21]([NH2:34])=[O:23])=[N:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred solution of methyl 7-[2-(6-cyanopyridin-3-yl)ethyl]-4-(2-fluoro-4-methoxyphenyl)quinoline-2-carboxylate (160 mg, 0.362 mmol) and MeOH (1450 μl) was treated with 5 ml 7N NH3/MeOH and then heated to 60° C. in a sealed tube for 30 minutes. The reaction was allowed to cool to ambient temperature and then was concentrated. The solid was trituated with EtOH, collected, washed with 5 ml Et2O and then dried in vacuo to afford 7-[2-(6-cyanopyridin-3-yl)ethyl]-4-(2-fluoro-4-methoxyphenyl)quinoline-2-carboxamide (105 mg, 0.246 mmol, 67.9% yield) as a colorless solid.

Workup

temperatureto cool to ambient temperature
concentrationwas concentrated
customcollected
washwashed with 5 ml Et2O
customdried in vacuo

Sources & evidence

ORD record: ord-0d93acef2ed541709a4fe39b51bf996c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278960B2

Reaction notes

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