Triethylamine → HCID 86630624, compound

HRID 643712Notes

Reaction equation

HRID 643712 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[CH3:34][S:35]([O:19][CH2:18][C:17]([S:14]([C:12]1[CH:11]=[CH:10][C:9]2[N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:6]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:7][C:8]=2[CH:13]=1)(=[O:16])=[O:15])([CH3:20])[CH3:21])(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 56669765HCID 56669765, compound

Product 1

HCID 86630624HCID 86630624, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropan-1-ol (Step H, 356 mg, 0.94 mmol) in dichloromethane (8 mL) were added triethylamine (157 μL, 1.13 mmol) and methanesulfonyl chloride (87 μL, 1.13 mmol) at 0° C. The mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with water (10 mL) and extracted with dichloromethane (30 mL×3). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford the crude title compound (411 mg) as yellow oil.

Workup

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with dichloromethane (30 mL×3)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adbfd09a574c46b29ca34de0b65f6351
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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