Formic Acid → HCID 71711234, compound

HRID 2403204Notes

Reaction equation

HRID 2403204 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].[CH:35](O)=[O:36].C(N1C=CN=C1)(N1C=CN=C1)=O>>[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]([CH:35]=[O:36])[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 284Formic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 71711171HCID 71711171, compound

Product 1

HCID 71711234HCID 71711234, compoundYield 67%

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) and formic acid (5.37 μL, 140 μmol) in methylenehloride (0.7 mL) was added carbonyldiimidazole (23.4 mg, 140 μmol). 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 (25 mg, 67%). MS ISP (m/e): 534.2/536.3 (100/29) [(M+H)]+.

Workup

  1. customThe reaction was purified by column chromatography on silica gel using a gradient from methylenechloride
  2. additionto a mixture of methylenechloride/methanol (v:v 19:1) as solvent

Sources & evidence

ORD record
ord-80cb399e6aec47d3bbdf8f4e7ef8e498
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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