Methanesulfonyl chloride → HCID 71711232, compound

HRID 2403202Notes

Reaction equation

HRID 2403202 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:16]([C:18]2([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH2:20][CH2:19]2)=[O:17])[C@H:13]([C:27]([NH:29][C:30]2([C:33]#[N:34])[CH2:32][CH2:31]2)=[O:28])[CH2:12]1)(=[O:10])=[O:9].[CH3:35][S:36](Cl)(=[O:38])=[O:37].C(N(C(C)C)C(C)C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:16]([C:18]2([N:21]3[CH2:22][CH2:23][N:24]([S:36]([CH3:35])(=[O:38])=[O:37])[CH2:25][CH2:26]3)[CH2:19][CH2:20]2)=[O:17])[C@H:13]([C:27]([NH:29][C:30]2([C:33]#[N:34])[CH2:31][CH2:32]2)=[O:28])[CH2:12]1)(=[O:10])=[O:9]

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 81531DiisopropylethylamineHCID 71711171HCID 71711171, compound

Product 1

HCID 71711232HCID 71711232, compoundYield 95.4%

Procedure

To a solution of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(piperazin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide (35.4 mg, 70 μmol) in methylenehloride (0.7 mL) was added under stirring ethyldiisopropyl amine (18.3 μL, 105 μmol) and methanesulfonyl chloride (6.00 μL, 77.0 μmol). The reaction was stirred at room temperature for 5 hours and additional ethyldiisopropyl amine (18.3 μL, 105 μmol) and methanesulfonyl chloride (6.00 μL, 77.0 μmol) was added. The reaction was stirred at room temperature over night. The reaction was purified by column chromatography on silica gel using ethyl acetate as solvent to yield the title compound as a yellow solid (39 mg, 95%). MS ISP (m/e): 584.1/586.1 (100/44) [(M+H)]+.

Workup

  1. stirringThe reaction was stirred at room temperature over night
  2. customThe reaction was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-32458d633d3048eca366adaf028624b7
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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