3-Aminopyridine → 4-oxo-N-(pyridin-3-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamide

HRID 876538Notes

Reaction equation

HRID 876538 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12](O)=[O:13])[CH:8]=[CH:9][CH:10]=2)[O:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[CH:3]1.[NH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=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:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12]([NH:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[O:13])[CH:8]=[CH:9][CH:10]=2)[O:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:16]=2)=[CH:3]1

Participants

6

Reactant 4

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584772184-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxylic acid

Product 1

HCID 584772124-oxo-N-(pyridin-3-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamideYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxylic acid 35 (0.5 g, 1.5 mmol), 3-aminopyridine 36 (0.28 g, 3 mmol), HATU (1.14 g, 3 mmol) and DIPEA (0.78 g, 6 mmol) in DMF (4 mL) was stirred at room temperature for 12 h. The reaction mixture was filtered and the solid was washed with H2O and dried under vacuum to give Compound 224 as a yellow solid (0.13 g, 23% yield). MS (ESI) calcd for C22H13F3N2O3: 410.09. found: 411 [M+H].

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with H2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d39bce9636a04980bfbaa002d3e27fe8
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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