Water → HCID 66631685, compound

HRID 714476Notes

Reaction equation

HRID 714476 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([OH:18])=[O:17])[CH:13]=[CH:14][CH:15]=2)[C:5]([C:19]#[N:20])=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[C:27]#[N:28].[NH2:29][CH2:30][C@@H:31]([OH:34])[CH2:32][OH:33].O>C1COCC1>[C:19]([C:5]1[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([OH:18])=[O:17])[CH:13]=[CH:14][CH:15]=2)=[N:7][C:2]([NH:29][CH2:30][C@@H:31]([OH:34])[CH2:32][OH:33])=[C:3]([C:27]#[N:28])[C:4]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)#[N:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6994409(2R)-3-aminopropane-1,2-diolHCID 86691917HCID 86691917, compound

Product 1

HCID 66631685HCID 66631685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

61.5 mg (0.15 mmol) of 3-{[(6-chloro-3,5-dicyano-4-phenylpyridin-2-yl)sulfanyl]methyl}benzenecarboxylic acid (Example 72A) were initially charged in 1.6 ml of THF. After addition of 27.6 mg (0.30 mmol) of (2R)-3-aminopropane-1,2-diol, the mixture was stirred at RT overnight. 2 ml of water were added, and the reaction mixture was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid).

Workup

  1. customthe reaction mixture was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-73a0b364301f4012b6510eaad92e63ac
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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