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

HRID 714477Notes

Reaction equation

HRID 714477 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([SH:22])[N:3]=1.Cl.Cl[CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([C:32]([NH:34][CH3:35])=[O:33])[CH:27]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([S:22][CH2:25][C:26]2[CH:31]=[CH:30][N:29]=[C:28]([C:32]([NH:34][CH3:35])=[O:33])[CH:27]=2)[C:5]([C:20]#[N:21])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=2)[C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 666315804-(chloromethyl)-N-methylpyridine-2-carboxamide hydrochlorideHCID 178510483HCID 178510483, compound

Product 1

HCID 565920944-[({6-Amino-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl}sulfanyl)methyl]-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.16 mmol) of 2-amino-4-[4-(2-hydroxyethoxy)phenyl]-6-sulfanylpyridine-3,5-dicarbonitrile (Example 10A), 38.9 mg (0.18 mmol) of 4-(chloromethyl)-N-methylpyridine-2-carboxamide hydrochloride (Example 41A) and 53.8 mg (0.64 mmol) of sodium bicarbonate were dissolved in 1 ml of DMF and the mixture was stirred at RT overnight. 30 ml of water were added to the reaction mixture, and the precipitate was filtered off. The precipitate was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid).

Workup

  1. filtrationthe precipitate was filtered off
  2. customThe precipitate was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-d2edac7a0fc041529b6ff3642cabaf8f
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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