Methoxyacetic Acid → N-[5-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-4-methyl-thiazol-2-yl]-2-methoxy-acetamide

HRID 1092989Notes

Reaction equation

HRID 1092989 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]([NH2:16])=[N:13][C:12]=2[CH3:17])=[CH:7][C:6]=1[C:18]([F:21])([F:20])[F:19])(=[O:4])=[O:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:46][O:47][CH2:48][C:49](O)=[O:50].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]([NH:16][C:49](=[O:50])[CH2:48][O:47][CH3:46])=[N:13][C:12]=2[CH3:17])=[CH:7][C:6]=1[C:18]([F:21])([F:20])[F:19])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 12251Methoxyacetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 574737494-Methyl-5-(4-(methylsulfonyl)-3-(trifluoromethyl)phenyl)thiazol-2-amine

Product 1

HCID 86598425N-[5-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-4-methyl-thiazol-2-yl]-2-methoxy-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-4-methyl-thiazol-2-ylamine (158a) (0.1 g, 0.3 mmol) is added to a solution of HATU (0.226 g, 0.6 mmol), methoxyacetic acid (0.046 ml, 0.6 mmol) and DIPEA (0.1 ml, 0.6 mmol) in DMF (7.5 ml). The reaction mixture was left to stir for 3 days at room temperature. The reaction mixture is filtered through basic alumina. The solvent is removed in vacuo and the product is purified by chromatography on silica eluting with ethyl acetate-hexane (3:1) to give the titled compound.

Workup

  1. waitThe reaction mixture was left
  2. filtrationThe reaction mixture is filtered through basic alumina
  3. customThe solvent is removed in vacuo
  4. customthe product is purified by chromatography on silica eluting with ethyl acetate-hexane (3:1)

Sources & evidence

ORD record
ord-613fbf8b1cef4e34a5da7e9ce1a2d44e
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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