Chlorosuccinimide → N-(4-(5-chloro-2-(((3,3-diphenylpropyl)(1-methylethyl)carbamoyl)amino)-1,3-thiazol-4-yl)phenyl)methanesulfonamide

HRID 2190342Notes

Reaction equation

HRID 2190342 reaction equation
[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:8][CH2:9][N:10]([CH:30]([CH3:32])[CH3:31])[C:11]([NH:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)[N:18]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:39]N1C(=O)CCC1=O>CN(C=O)C>[Cl:39][C:16]1[S:15][C:14]([NH:13][C:11](=[O:12])[N:10]([CH2:9][CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:30]([CH3:31])[CH3:32])=[N:18][C:17]=1[C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 251744811-(3,3-Diphenylpropyl)-1-isopropyl-3-(4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)urea

Product 1

HCID 25175474N-(4-(5-chloro-2-(((3,3-diphenylpropyl)(1-methylethyl)carbamoyl)amino)-1,3-thiazol-4-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3,3-diphenylpropyl)-1-isopropyl-3-(4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)urea (0.101 g, 0.18 mmol) in DMF (1 mL) at room temperature was added 1-chloropyrrolidine-2,5-dione (0.035 g, 0.26 mmol). The reaction mixture was stirred at room temperature for 2 d. Direct purification by flash column chromatography on silica gel (eluted with 20% to 60% EtOAc in hexanes) gave N-(4-(5-chloro-2-(((3,3-diphenylpropyl)(1-methylethyl)carbamoyl)amino)-1,3-thiazol-4-yl)phenyl)methanesulfonamide 69. Mass spectrum, calculated for C29H31ClN4O3S2 582.2; found 583.1 (M++1).

Workup

  1. customDirect purification by flash column chromatography on silica gel (eluted with 20% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-69688ed3da4c4233b0449b5e4213df31
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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