Methanol → HCID 69211308, compound

HRID 2252078Notes

Reaction equation

HRID 2252078 reaction equation
[BH4-].[Na+].[CH:3]([S:6]([N:9]1[C:13]2[CH:14]=[C:15]([C:18]3[N:22]([CH:23]4[CH2:28][CH2:27]C(=O)[CH2:25][CH2:24]4)[CH:21]=[N:20][C:19]=3C3C=CC=CC=3)[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH2:36])(=[O:8])=[O:7])([CH3:5])[CH3:4].[CH3:37][OH:38]>O1CCCC1.O>[CH:3]([S:6]([N:9]1[C:13]2[CH:14]=[C:15]([C:18]3[N:22]([CH:23]4[CH2:24][CH2:25][CH:37]([OH:38])[CH2:27][CH2:28]4)[C:21]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:20][CH:19]=3)[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH2:36])(=[O:7])=[O:8])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 887Methanol2×HCID 4311764Sodium borohydrideHCID 17981638HCID 17981638, compound

Product 1

HCID 69211308HCID 69211308, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of sodium borohydride (0.28 g) in methanol (5 mL) to a solution of 1-isopropylsulfonyl-2-amino-6-(1-(cyclohexan-1-on-4-yl)-4(phenyl)-imidazol-5-yl)-benzimidazole (0.35 g, 0.7 mmol) in 10 mL tetrahydrofuran and 10 mL methanol. Stir the reaction mixture for 30 minutes at room temperature, dilute with water (50 mL), and extract with ethyl acetate (2×15 mL). Wash the combined organic extracts with saturated aqueous sodium chloride, dry over sodium sulfate, and concentrate under reduced pressure to provide 0.345 g (98%) of the title compound. MS(ES+): m/z=480.2 (M+H)+

Workup

  1. extractionextract with ethyl acetate (2×15 mL)
  2. washWash the combined organic extracts with saturated aqueous sodium chloride
  3. dry with materialdry over sodium sulfate
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-28db2690e4974564ae4090df8dd71aa5
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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