Water → HCID 68869754, compound

HRID 1817862Notes

Reaction equation

HRID 1817862 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH2:14]O)=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:3][CH2:2]1.CS([Cl:25])(=O)=O.C(N(CC)CC)C.O>ClCCl>[Cl:25][CH2:14][C:12]1[CH:11]=[CH:10][C:9]2[N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:6]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:7][C:8]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68874198HCID 68874198, compound

Product 1

HCID 68869754HCID 68869754, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]methanol (Step D, 200 mg, 0.73 mmol) in dichloromethane (3 mL) were added methanesulfonyl chloride (114 μL, 1.5 mmol) and triethylamine (226 μL, 1.6 mmol) at 0° C. The mixture was stirred at 0° C. for 1 h and at room temperature for 2 h. Water (2 mL) was added and the mixture was extracted with ethyl acetate (10 mM×2). The organic extracts were dried over sodium sulfate and concentrated to afford the title compound as pale red oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (10 mM×2)
  2. dry with materialThe organic extracts were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e354909cc867448a9677c327c8eec6ba
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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