2-Bromo-N-(5-chloro-2-pyridinyl)acetamide → 5-Chloro-thiophene-2-carboxylic acid {2-[[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide

HRID 416542Notes

Reaction equation

HRID 416542 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][N:7]=1)=[O:4].[CH:13]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][S:23]([CH2:26][CH2:27][NH:28][C:29]([C:31]2[S:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[O:30])(=[O:25])=[O:24])[CH2:18][CH2:17]1)([CH3:15])[CH3:14]>>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3]([CH2:2][N:22]([CH:19]2[CH2:20][CH2:21][N:16]([CH:13]([CH3:15])[CH3:14])[CH2:17][CH2:18]2)[S:23]([CH2:26][CH2:27][NH:28][C:29]([C:31]2[S:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[O:30])(=[O:24])=[O:25])=[O:4])=[N:7][CH:8]=1

Participants

3

Reactant 2

HCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 666246505-Chloro-thiophene-2-carboxylic acid {2-[[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 15 starting from 168 mg (2 equiv.) 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide and 133 mg (0.34 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-[[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-(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-[[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-(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-fbab976374ea4704b1fc8041b342ce60
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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