Water → 4-{[(6-Amino-3,5-dicyano-4-phenylpyridin-2-yl)sulfanyl]methyl}-N-methylpyridine-2-carboxamide

HRID 714470Notes

Reaction equation

HRID 714470 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([SH:18])[N:3]=1.Cl.Cl[CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([C:28]([NH:30][CH3:31])=[O:29])[CH:23]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([S:18][CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([C:28]([NH:30][CH3:31])=[O:29])[CH:23]=2)[C:5]([C:16]#[N:17])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 666315804-(chloromethyl)-N-methylpyridine-2-carboxamide hydrochlorideHCID 178510474HCID 178510474, compound

Product 1

HCID 565920084-{[(6-Amino-3,5-dicyano-4-phenylpyridin-2-yl)sulfanyl]methyl}-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.00 g (3.96 mmol) of 2-amino-4-phenyl-6-sulfanylpyridine-3,5-dicarbonitrile (Example 30A), 0.96 g (4.36 mmol) of 4-(chloromethyl)-N-methylpyridine-2-carboxamide hydrochloride (Example 41A) and 1.33 g (15.84 mmol) of sodium bicarbonate were dissolved in 20 ml of DMF and the mixture was stirred at RT for 2 h. 500 ml of water were added to the reaction mixture. The precipitate was filtered off and washed with water.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water

Sources & evidence

ORD record
ord-43e259f8ac124f5fad3246c20a1c7c6b
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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