Sodium borohydride → HCID 25270557, compound

HRID 1516405Notes

Reaction equation

HRID 1516405 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:36])(=[N:29][CH2:30][C:31](OCC)=[O:32])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.[BH4-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:36])(=[N:29][CH2:30][CH2:31][OH:32])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86652062HCID 86652062, compound

Product 1

HCID 25270557HCID 25270557, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring solution of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-methyl-N-(ethoxycarbonyl methyl)sulfoximide (1.3 g, 0.00237 mol) in DMSO (4 mL) was added Sodium borohydride (360 mg, 0.00948 mol) at 60° C. in several lots. Reaction mixture was stirred at same temperature for 5 hr. Subsequent work up and column purification (100-200 mesh silica gel, 2% methanol in chloroform) gave 400 mg of titled product in 80% yield.

Workup

  1. customReaction mixture
  2. customSubsequent work up and column purification (100-200 mesh silica gel, 2% methanol in chloroform)

Sources & evidence

ORD record
ord-e8c79eb1f5bf400fb9e00cdaa6decd47
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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