Methanesulfonyl chloride → HCID 57670022, compound

HRID 1894516Notes

Reaction equation

HRID 1894516 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([N:10]2[C@@:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)([CH3:15])[C@@:13]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)([CH3:23])[N:12]=[C:11]2[C:31]2[CH:32]=[N:33][C:34]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:35][C:36]=2[O:37][CH2:38][CH3:39])=[O:9])[CH2:3][CH2:2]1.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>ClCCl>[CH3:44][S:45]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]([N:10]2[C@@:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)([CH3:15])[C@@:13]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)([CH3:23])[N:12]=[C:11]2[C:31]2[CH:32]=[N:33][C:34]([C:40]([CH3:42])([CH3:41])[CH3:43])=[CH:35][C:36]=2[O:37][CH2:38][CH3:39])=[O:9])[CH2:5][CH2:6]1)(=[O:47])=[O:46]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67206259HCID 67206259, compound

Product 1

HCID 57670022HCID 57670022, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carboxylic acid piperidin-4-yl amide (56.5 mg, 0.091 mmole) in dichloromethane (6 mL) was treated with methanesulfonyl chloride (26.0 mg, 0.226 mmole, Aldrich) at 0° C. and allowed to stir for 1 h before diluted with dichloromethane (60 mL), washed with aqueous sodium carbonate (15 mL), water (15 mL) and concentrated. The residue was purified by flash column chromatography (silica gel, eluting with a gradient of 1-10% methanol in dichloromethane) to give the title compound (59.5 mg). HR-MS (ES, m/z) calculated for C35H44Cl2N5O4S [(M+H)+] 700.2486, observed 700.2482.

Workup

  1. washwashed with aqueous sodium carbonate (15 mL), water (15 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography (silica gel
  4. washeluting with a gradient of 1-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5e01269647c344b69596aff71c264022
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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