2-(Chloromethyl)-5-cyclopropyl-1,3,4-thiadiazole → 5-Chloro-thiophene-2-carboxylic acid {2-[(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide

HRID 416541Notes

Reaction equation

HRID 416541 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]([CH:8]2[CH2:10][CH2:9]2)=[N:6][N:7]=1.[CH:11]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][S:21]([CH2:24][CH2:25][NH:26][C:27]([C:29]2[S:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[O:28])(=[O:23])=[O:22])[CH2:16][CH2:15]1)([CH3:13])[CH3:12]>>[CH:8]1([C:5]2[S:4][C:3]([CH2:2][N:20]([CH:17]3[CH2:18][CH2:19][N:14]([CH:11]([CH3:13])[CH3:12])[CH2:15][CH2:16]3)[S:21]([CH2:24][CH2:25][NH:26][C:27]([C:29]3[S:30][C:31]([Cl:34])=[CH:32][CH:33]=3)=[O:28])(=[O:22])=[O:23])=[N:7][N:6]=2)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 27576792-(Chloromethyl)-5-cyclopropyl-1,3,4-thiadiazoleHCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 666248035-Chloro-thiophene-2-carboxylic acid {2-[(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 15 starting from 89 mg (2 equiv.) 2-chloromethyl-5-cyclopropyl-[1,3,4]thiadiazole 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-cyclopropyl-[1,3,4]thiadiazol-2-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-cyclopropyl-[1,3,4]thiadiazol-2-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-03f586182a494301b1e6a81263464d3d
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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