Methanesulfonyl chloride → 1-(4-((1H-Benzo[d]imidazol-2-yl)methyl)benzoyl)pyrrolidin-3-yl Methanesulfonate

HRID 1163086Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A portion of [4-(1H-benzoimidazol-2-ylmethyl)-phenyl]-(3-hydroxy-pyrrolidin-1-yl)-methanone (1.00 g, 3.1 mmol) was dissolved in dichloromethane, treated with diisopropylethylamine (0.60 g, 4.6 mmol), cooled to 0° C., treated dropwise with a solution of methanesulfonyl chloride (0.49 g, 4.3 mmol) in dichloromethane, stirred at 0° C. for 10 min. and concentrated under vacuum to provide a solid residue. Purification of this residue by column chromatography (silica, chloroform:methanol 0→5%) gave the title product as a yellow solid (62%). 1H NMR (400 MHz, CDCl3): 7.58 (m, 2H), 7.56 (m, 4H), 7.22 (m, 2H), 5.27 (d, J=5.4 Hz 1H), 4.35 (s, 2H), 3.93 (s, 1H), 3.80 (s, 1H), 3.63 (m, 4H), 3.09 (m, 3H), 2.31 (m, 2H). [M+H] 400.

Workup

concentrationconcentrated under vacuum
customto provide a solid residue
customPurification of this residue by column chromatography (silica, chloroform:methanol 0→5%)

Sources & evidence

ORD record: ord-c8182bb8f247486b92a678e26de33206
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820825B2

Reaction notes

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