Dimethylformamide → ethyl 2-(3-cyano-2-cyclohexyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

HRID 1189533Notes

Reaction equation

HRID 1189533 reaction equation
[CH:1]1([C:7]2[N:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([CH3:18])=[C:9]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[S:26]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)(=[O:28])=[O:27])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClS([N:38]=[C:39]=O)(=O)=O.CN(C)C=O>>[C:39]([C:8]1[C:9]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[S:26]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)(=[O:27])=[O:28])=[C:10]([CH3:18])[N:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]=1[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)#[N:38]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 53247598ethyl 2-(5-cyclohexyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

Product 1

HCID 53247599ethyl 2-(3-cyano-2-cyclohexyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetateYield 72%

Procedure

General procedure II was followed using ethyl 2-(5-cyclohexyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (642 mg, 1.36 mmol), chlorosulfonyl isocyanate (0.147 mL, 1.70 mmol) and N,N-dimethylformamide (0.105 mL, 1.36 mmol) to afford ethyl 2-(3-cyano-2-cyclohexyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (485 mg, 0.975 mmol, 72% yield) as a white sticky foam.

Sources & evidence

ORD record
ord-3bb15c13cc16474d9191e807b6e82392
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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