3-(Chloromethyl)-5-methyl-1,2-oxazole → HCID 66624553, compound

HRID 416514Notes

Reaction equation

HRID 416514 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[CH:9]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][S:19]([CH2:22][CH2:23][NH:24][C:25]([C:27]2[S:28][C:29]([Cl:32])=[CH:30][CH:31]=2)=[O:26])(=[O:21])=[O:20])[CH2:14][CH2:13]1)([CH3:11])[CH3:10]>>[CH:9]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]([CH2:2][C:3]2[CH:7]=[C:6]([CH3:8])[O:5][N:4]=2)[S:19]([CH2:22][CH2:23][NH:24][C:25]([C:27]2[S:28][C:29]([Cl:32])=[CH:30][CH:31]=2)=[O:26])(=[O:20])=[O:21])[CH2:14][CH2:13]1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazoleHCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 66624553HCID 66624553, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-(5-methyl-isoxazol-3-ylmethyl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 15 starting from 67 mg (1 equiv.) 3-chloromethyl-5-methyl-isoxazole and 200 mg (0.50 mmol) 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide (reaction temperature: 60° C.). Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-(5-methyl-isoxazol-3-ylmethyl)-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-[(1-isopropyl-piperidin-4-yl)-(5-methyl-isoxazol-3-ylmethyl)-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-ccc572995e664c4b9d63cfb25dfac7d0
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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