Hydrogen Bromide → HCID 86603173, compound

HRID 1818939Notes

Reaction equation

HRID 1818939 reaction equation
Br.[CH3:2][O:3][C:4](=[O:12])[CH2:5][C:6]1[S:10][C:9]([NH2:11])=[N:8][CH:7]=1.CCN(C(C)C)C(C)C.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:25]=[C:26]([N:30]=[C:31]=[O:32])[CH:27]=[CH:28][CH:29]=1>CN(C=O)C>[CH3:2][O:3][C:4](=[O:12])[CH2:5][C:6]1[S:10][C:9]([NH:11][C:31]([NH:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:22])([F:33])[F:34])[CH:25]=2)=[O:32])=[N:8][CH:7]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 81531DiisopropylethylamineHCID 963498(2-Amino-thiazol-5-yl)-acetic acid methyl ester2×

Product 1

HCID 86603173HCID 86603173, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the HBr salt of (2-amino-thiazol-5-yl)-acetic acid methyl ester (compound 44.1; 20 mmol) in DIEA (40 mmol) and DMF (100 mL) was added 3-trifluoromethylphenyl isocyanate (20 mmol) at room temperature. After overnight stirring, the reaction mixture was concentrated and purified by flash column chromatography on silica gel to provide {2-[3-(3-trifluoromethyl-phenyl)-ureido]-thiazol-5-yl}-acetic acid methyl ester (compound 44.2) in 60% yield. EIMS (m/z): calcd. for C14H12F3N3O3S (M+)+H 360.06. found 360.10.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f772de62016d43baa0256405cc22961f
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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