(5-Methyl-3-phenyl-4-isoxazolyl)methylamine → 2-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-thiazole-5-carboxylic acid (tetra-hydro-pyran-4-yl)-amide

HRID 1923649Notes

Reaction equation

HRID 1923649 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][NH2:14].[O:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]([C:24]2[S:28][C:27](Cl)=[N:26][CH:25]=2)=[O:23])[CH2:17][CH2:16]1>CN(C=O)C>[O:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]([C:24]2[S:28][C:27]([NH:14][CH2:13][C:3]3[C:4]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:5][O:6][C:2]=3[CH3:1])=[N:26][CH:25]=2)=[O:23])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 2776151(5-Methyl-3-phenyl-4-isoxazolyl)methylamineHCID 666437572-Chloro-N-(tetrahydro-2H-pyran-4-yl)thiazole-5-carboxamide

Product 1

HCID 497809292-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-thiazole-5-carboxylic acid (tetra-hydro-pyran-4-yl)-amideYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of (5-methyl-3-phenyl-4-isoxazolyl)methylamine (100 mg, 0.53 mmol) and 2-chloro-thiazole-5-carboxylic acid (tetrahydro-pyran-4-yl)-amide (131 mg, 0.53 mmol) in DMF (3 mL) was heated at 150° C. under microwave irradiation for 1 h. The reaction mixture was cooled and concentrated in vacuo, then purified by chromatography (silica, 0 to 3% methanol in dichloromethane) to give the title compound (12 mg, 6%) as a white solid. MS: m/e=399.1 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography (silica, 0 to 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-04e4c51fa9dd4eaa9ebd8a249d767467
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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