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

HRID 1189542Notes

Reaction equation

[CH:1]1([C:4]2[N:8]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:7]([CH3:15])=[C:6]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)(=[O:25])=[O:24])[CH:5]=2)[CH2:3][CH2:2]1.ClS([N:35]=[C:36]=O)(=O)=O.CN(C)C=O>>[C:36]([C:5]1[C:6]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([N:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)(=[O:24])=[O:25])=[C:7]([CH3:15])[N:8]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]=1[CH:1]1[CH2:3][CH2:2]1)#[N:35]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 70918Chlorosulfonyl isocyanate

HCID 58310978ethyl 2-(5-cyclopropyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

Product 1

HCID 53247601ethyl 2-(3-cyano-2-cyclopropyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetateYield 5%

Procedure

General procedure II was followed using ethyl 2-(5-cyclopropyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (1.09 g, 2.53 mmol), chlorosulfonyl isocyanate (0.275 mL, 3.16 mmol) and N,N-dimethylformamide (0.196 mL, 2.53 mmol) to afford ethyl 2-(3-cyano-2-cyclopropyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (58.0 mg, 0.127 mmol, 5% yield) as a viscous oil. 1D-NOESY experiment was performed to confirm the drawn regioisomer (irradiation of methyl group and 1-2% interaction with both methylene groups).

Sources & evidence

ORD record: ord-7b320af977124a22adbe9b1f7ae6d837
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674115B2

Reaction notes

Loading…