Acetone → HCID 59302985, compound

HRID 1692134Notes

Reaction equation

HRID 1692134 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 MI) 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-83f5634c12954faeb158c77944b5cd25
Source dataset
uspto-grants-2012_04
Patent number
US08153818B2

Reaction notes

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