Acetyl chloride → HCID 71711172, compound

HRID 2403201Notes

Reaction equation

HRID 2403201 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].[C:35](Cl)(=[O:37])[CH3:36].C(N(C(C)C)C(C)C)C>>[C:35]([N:24]1[CH2:23][CH2:22][N:21]([C:18]2([C:16]([N:14]3[CH2:15][C@H:11]([S:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])(=[O:10])=[O:9])[CH2:12][C@H:13]3[C:27]([NH:29][C:30]3([C:33]#[N:34])[CH2:31][CH2:32]3)=[O:28])=[O:17])[CH2:19][CH2:20]2)[CH2:26][CH2:25]1)(=[O:37])[CH3:36]

Participants

4

Reactant 3

HCID 6367Acetyl chloride2×HCID 81531DiisopropylethylamineHCID 71711171HCID 71711171, compound

Product 1

HCID 71711172HCID 71711172, compoundYield 70%

Procedure

To a solution of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(piperazin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide (38 mg, 75.1 μmol) in methylenehloride (0.75 mL) was added under stirring ethyldiisopropyl amine (19.7 μL, 113 μmol) and acetyl chloride (5.99 μL, 82.6 μmol). The reaction was stirred at room temperature for 5 hours and additional ethyldiisopropyl amine (19.7 μL, 113 μmol) and acetyl chloride (5.99 μL, 82.6 μmol) was added. The reaction was stirred at room temperature over night. The reaction was purified by column chromatography on silica gel using a gradient from methylenechloride to a mixture of methylenechloride/methanol (v:v 19:1) as solvent to yield the title compound as a white solid (28.8 mg, 70%). MS ISP (m/e): 548.3/550.4 (100/41) [(M+H)]+.

Workup

  1. stirringThe reaction was stirred at room temperature over night
  2. customThe reaction was purified by column chromatography on silica gel using a gradient from methylenechloride
  3. additionto a mixture of methylenechloride/methanol (v:v 19:1) as solvent

Sources & evidence

ORD record
ord-34a86f40e18447dca1bafb085cf22c60
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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