3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole → 5-Chloro-thiophene-2-carboxylic acid {2-[[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide

HRID 416540Notes

Reaction equation

HRID 416540 reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[S:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[O:5][N:4]=1.[CH:14]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][S:24]([CH2:27][CH2:28][NH:29][C:30]([C:32]2[S:33][C:34]([Cl:37])=[CH:35][CH:36]=2)=[O:31])(=[O:26])=[O:25])[CH2:19][CH2:18]1)([CH3:16])[CH3:15]>>[Cl:13][C:10]1[S:9][C:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][N:23]([CH:20]3[CH2:21][CH2:22][N:17]([CH:14]([CH3:16])[CH3:15])[CH2:18][CH2:19]3)[S:24]([CH2:27][CH2:28][NH:29][C:30]([C:32]3[S:33][C:34]([Cl:37])=[CH:35][CH:36]=3)=[O:31])(=[O:25])=[O:26])[CH:7]=2)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 666249695-Chloro-thiophene-2-carboxylic acid {2-[[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 15 starting from 141 mg (2 equiv.) 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole 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-[[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-(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-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-(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-3b443c1147da4778a8ad710553eb52b7
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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