3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole → 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-6-(2,2,2-trifluoro-ethoxy)-3H-thieno[3,4-d]imidazole-4-carboxylic acid methyl ester

HRID 18593Notes

Reaction equation

HRID 18593 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[C:8]2[C:12]=1[NH:11][C:10]([C:13](=[O:24])[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]1)=[N:9]2)=[O:4].Br[CH2:32][C:33]1[CH:37]=[C:36]([C:38]2[S:39][C:40]([Cl:43])=[CH:41][CH:42]=2)[O:35][N:34]=1>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([O:25][CH2:26][C:27]([F:28])([F:29])[F:30])=[C:8]2[C:12]=1[N:11]([CH2:32][C:33]1[CH:37]=[C:36]([C:38]3[S:39][C:40]([Cl:43])=[CH:41][CH:42]=3)[O:35][N:34]=1)[C:10]([C:13](=[O:24])[NH:14][CH:15]1[CH2:16][CH2:17][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:19][CH2:20]1)=[N:9]2)=[O:4]

Participants

3

Reactant 2

HCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 178499368HCID 178499368, compound

Product 1

HCID 670122883-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-6-(2,2,2-trifluoro-ethoxy)-3H-thieno[3,4-d]imidazole-4-carboxylic acid methyl ester

Procedure

3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-6-(2,2,2-trifluoro-ethoxy)-3H-thieno[3,4-d]imidazole-4-carboxylic acid methyl ester was prepared by a procedure according to example 81 starting from 68.0 mg (0.15 mmol) 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-6-(2,2,2-trifluoro-ethoxy)-3H-thieno[3,4-d]imidazole-4-carboxylic acid methyl ester and 42.2 mg (0.15 mmol) 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole. Purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave the title compound as its formiate in form of a white amorphous solid. Structural assignment was achieved by NOE-spectroscopy.

Workup

  1. custom3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-6-(2,2,2-trifluoro-ethoxy)-3H-thieno[3,4-d]imidazole-4-carboxylic acid methyl ester was prepared by a procedure
  2. customPurification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid)

Sources & evidence

ORD record
ord-2e5a3993b02240c498548cc55dd23f06
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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