Methyl 3-(chlorosulfonyl)propanoate → 3-({2-[3-(2-Cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-sulfamoyl)-propionic acid methyl ester

HRID 559922Notes

Reaction equation

HRID 559922 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[C:19]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])=[O:10])[S:6][CH:7]=1.[CH3:26][O:27][C:28](=[O:35])[CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32]>>[CH3:26][O:27][C:28](=[O:35])[CH2:29][CH2:30][S:31](=[O:33])(=[O:32])[NH:1][CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[C:19]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])=[O:10])[S:6][CH:7]=1

Participants

3

Reactant 2

HCID 4962888Methyl 3-(chlorosulfonyl)propanoateHCID 597328161-(4-Aminomethyl-thiazol-2-yl)-3-(2-cyclopentanecarbonyl-4-methylphenyl)-urea

Product 1

HCID 597328333-({2-[3-(2-Cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-sulfamoyl)-propionic acid methyl esterYield 91.2%

Procedure

3-({2-[3-(2-Cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-sulfamoyl)-propionic acid methyl ester (116 mg, 91%) was prepared from 1-(4-aminomethyl-thiazol-2-yl)-3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-urea (90 mg, 0.25 mmol) and 3-chlorosulfonyl-propionic acid methyl ester (47 mg, 0.25 mmol) following the general procedure T.

Sources & evidence

ORD record
ord-fe2e911598984711ba9b9af7a8e67d2f
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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