Diisopropylethylamine → N-(4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromen-8-yl)thiazole-4-carboxamide

HRID 876522Notes

Reaction equation

HRID 876522 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[CH:8][C:7]2=[O:22].[S:23]1[CH:27]=[C:26]([C:28](O)=[O:29])[N:25]=[CH:24]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[O:22]=[C:7]1[C:6]2[C:11](=[C:2]([NH:1][C:28]([C:26]3[N:25]=[CH:24][S:23][CH:27]=3)=[O:29])[CH:3]=[CH:4][CH:5]=2)[O:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)=[CH:8]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 3042714-Thiazolecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584772718-amino-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one

Product 1

HCID 58477258N-(4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromen-8-yl)thiazole-4-carboxamideYield 29.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8-amino-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one (178) (70 mg, 0.23 mmol) was taken up in 2 mL of DMF along with thiazole-4-carboxylic acid 3 (30 mg, 0.23 mmol), HATU (175 mg, 0.46 mmol) and DIEA (80 μL, 0.46 mmol). The reaction mixture was stirred at room temperature for 18 h. It was then diluted with 5 mL of H2O. The resulting solids were collected by filtration, washed successively with a solution of dilute NaHCO3/MeOH (1:1), aqueous MeOH, dilute 1 N HCl/MeOH (1:1), aqueous MeOH, and then pure MeOH. After drying under high vacuum, 28 mg of Compound 204 was obtained as an off-white solid. MS (ESI) calcd for C20H11F3N2O3S: 416.04. found: 417 [M+H].

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. washwashed successively with a solution of dilute NaHCO3/MeOH (1:1), aqueous MeOH
  3. additiondilute 1 N HCl/MeOH (1:1), aqueous MeOH
  4. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-74e10d83798d46d88c32a0b763042a01
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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