Water → 4-({[6-amino-3,5-dicyano-4-(4-fluorophenyl)pyridin-2-yl]oxy}methyl)-N-methylpyridine-2-carboxamide

HRID 714475Notes

Reaction equation

CC(C)([O-])C.[K+].O.Cl.[OH:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH:19][CH3:20])=[O:18])[CH:12]=1.[NH2:21][C:22]1[C:27]([C:28]#[N:29])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:25]([C:37]#[N:38])=[C:24](SC2C=CC=CC=2)[N:23]=1.O>COCCOC>[NH2:21][C:22]1[N:23]=[C:24]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH:19][CH3:20])=[O:18])[CH:12]=2)[C:25]([C:37]#[N:38])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:27]=1[C:28]#[N:29]

Participants

Conditions

Temperature: 60 °C

Procedure

1.62 g (14.44 mmol) of potassium tert-butoxide were suspended in 10 ml of 1,2-dimethoxyethane. After addition of 1.44 g (8.66 mmol) of 4-(hydroxymethyl)-N-methylpyridine-2-carboxamide hydrochloride monohydrate (Example 40A) and 1.00 g (2.89 mmol) of 2-amino-4-[4-fluorophenyl]-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile (Example 38A), the mixture was stirred at 60° C. for 2 h and at RT overnight. 30 ml of water were added to the reaction mixture. The precipitate was filtered off and washed with water.

Workup

filtrationThe precipitate was filtered off
washwashed with water

Sources & evidence

ORD record: ord-65e7bb050b2d4d8da5ff9215051d3197
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187428B2

Reaction notes

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