Triethylamine → HCID 58970771, compound

HRID 1163075Notes

Reaction equation

HRID 1163075 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:26]=[CH:25][C:16]([C:17]([N:19]4[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]4)=[O:18])=[CH:15][CH:14]=3)[C:10]3[CH:27]=[CH:28][CH:29]=[CH:30][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:26]=[CH:25][C:16]([C:17]([N:19]4[CH2:23][CH2:22][CH:21]([O:24][S:39]([CH3:38])(=[O:41])=[O:40])[CH2:20]4)=[O:18])=[CH:15][CH:14]=3)[C:10]3[CH:27]=[CH:28][CH:29]=[CH:30][C:9]=3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58970777HCID 58970777, compound

Product 1

HCID 58970771HCID 58970771, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{4-[(2-phenyl-1H-benzimidazol-1-yl)methyl]benzoyl}pyrrolidin-3-ol (0.85 g, 3 mmol) in DCM at 0° C. is treated with and triethylamine (0.91 mL, 6.6 mmol) followed by methylsulfonyl chloride (0.25 mL, 3.3 mmol), stirred at room temperature overnight and concentrated to give methanesulfonic acid 1-[4-(2-phenyl-benzoimidazol-1-ylmethyl)-benzoyl]-pyrrolidin-3-yl ester as a white powder (1.4 g) identified by HPLC and MS [476.3 m/e (M+H)].

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-73fe5f3ebab34cd5b433866ee88cefce
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

Loading…