Acetone → HCID 59302985, compound

HRID 448112Notes

Reaction equation

HRID 448112 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[C:22]2[N:26]([C@H:27]3[CH2:31][CH2:30][NH:29][CH2:28]3)[CH:25]=[N:24][N:23]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:32][C:33]([CH3:35])=O.[BH3-]C#N.[Na+]>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[C:22]2[N:26]([C@H:27]3[CH2:31][CH2:30][N:29]([CH:33]([CH3:35])[CH3:32])[CH2:28]3)[CH:25]=[N:24][N:23]=2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 59302978HCID 59302978, compound

Product 1

HCID 59302985HCID 59302985, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled solution of 4-tert-butyl-N-[4-chloro-2-((S)-4-pyrrolidin-3-yl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide (200 mg, 0.43 mmol) in MeOH (5 Ml) was added acetone (0.048 mL, 0.65 mmol) and then NaCNBH3 (0.054 g, 0.86 mmol). The reaction mixture was stirred at room temperature for 2 h, evaporated to dryness, adsorbed onto silica gel, and purified by automated normal-phase chromatography (50% MeOH in EtOAc) and then preparative HPLC (20→95% CH3CN in H2O with 0.1% TFA). The pure fractions were combined and lyophilized to obtain title compound as a powder: MS (ES) M+H expected 502.0, found 502.1.

Workup

  1. customevaporated to dryness
  2. custompurified by automated normal-phase chromatography (50% MeOH in EtOAc)

Sources & evidence

ORD record
ord-244307cb355844309c3639b1a2f9792d
Source dataset
uspto-grants-2013_07
Patent number
US08481579B2

Reaction notes

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