Chloroacetamide → HCID 11957760, compound

HRID 416513Notes

Reaction equation

HRID 416513 reaction equation
Cl[CH2:2][C:3]([NH2:5])=[O:4].[CH:6]([N:9]1[CH2:14][CH2:13][CH:12]([NH:15][S:16]([CH2:19][CH2:20][NH:21][C:22]([C:24]2[S:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[O:23])(=[O:18])=[O:17])[CH2:11][CH2:10]1)([CH3:8])[CH3:7]>>[C:3]([CH2:2][N:15]([CH:12]1[CH2:13][CH2:14][N:9]([CH:6]([CH3:8])[CH3:7])[CH2:10][CH2:11]1)[S:16]([CH2:19][CH2:20][NH:21][C:22]([C:24]1[S:25][C:26]([Cl:29])=[CH:27][CH:28]=1)=[O:23])(=[O:17])=[O:18])(=[O:4])[NH2:5]

Participants

3

Reactant 2

HCID 6580ChloroacetamideHCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 11957760HCID 11957760, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[carbamoylmethyl-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 15 starting from 48 mg (2 equiv.) 2-chloro-acetamide and 100 mg (0.25 mmol) 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-chloro-thiophene-2-carboxylic acid {2-[carbamoylmethyl-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide. The title compound was obtained as its trifluoroacetate in form of a colorless amorphous material.

Workup

  1. custom5-Chloro-thiophene-2-carboxylic acid {2-[carbamoylmethyl-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure
  2. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA)

Sources & evidence

ORD record
ord-68cb3c165685488081f84a243af85ec6
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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