2-Aminothiazole → N-(thiazol-2-yl)-3-(3-(trifluoromethoxy)phenyl)quinoxaline-5-carboxamide

HRID 2359420Notes

Reaction equation

HRID 2359420 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[N:12][C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([C:20](O)=[O:21])[C:18]=3[N:19]=2)[CH:7]=[CH:8][CH:9]=1.[NH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=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>[S:27]1[CH:28]=[CH:29][N:30]=[C:26]1[NH:25][C:20]([C:17]1[C:18]2[N:19]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:1])([F:23])[F:24])[CH:5]=3)[CH:11]=[N:12][C:13]=2[CH:14]=[CH:15][CH:16]=1)=[O:21]

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581545253-(3-(Trifluoromethoxy)phenyl)quinoxaline-5-carboxylic acid

Product 1

HCID 58154628N-(thiazol-2-yl)-3-(3-(trifluoromethoxy)phenyl)quinoxaline-5-carboxamideYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(3-(trifluoromethoxy)phenyl)quinoxaline-5-carboxylic acid (100 mg, 0.30 mmol), 2-aminothiazole (30 mg, 0.30 mmol), HATU (171 mg, 0.45 mmol) and DIEA (116 mg, 0.9 mmol) in DMF (10 mL) was stirred at room temperature for 2 h. Water (20 mL) was added, and the resulting precipitate was collected by filtration and dried under vacuum to give N-(thiazol-2-yl)-3-(3-(trifluoromethoxy)phenyl)quinoxaline-5-carboxamide as a solid (115.5 mg, 92% yield). MS (ESI) calcd for C19H11F3N4O2S (m/z): 416.06. found: 417 [M+1].

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-762b4417a5234396ae74c11be648e1e4
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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