2-Pyrazinecarboxylic acid → HCID 58154679, compound

HRID 2359434Notes

Reaction equation

HRID 2359434 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:43][C:44]1[CH:45]=[C:46]([C:54]2[CH:63]=[CH:62][C:61]3[C:56](=[C:57]([NH2:64])[CH:58]=[CH:59][CH:60]=3)[N:55]=2)[CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=1>CN(C=O)C.O>[F:43][C:44]1[CH:45]=[C:46]([C:54]2[CH:63]=[CH:62][C:61]3[C:56](=[C:57]([NH:64][C:7]([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)=[O:9])[CH:58]=[CH:59][CH:60]=3)[N:55]=2)[CH:47]=[C:48]([C:50]([F:52])([F:53])[F:51])[CH:49]=1

Participants

7

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58154634HCID 58154634, compound

Product 1

HCID 58154679HCID 58154679, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-pyrazine carboxylic acid (0.065 g, 0.51 mmol) was combined with DIPEA (0.140 mL, 0.811 mmol) and HATU (0.200 g, 0.51 mmol) in 5 mL DMF. The mixture was stirred at room temperature for ten minutes, at which time 2-(3-fluoro-5-(trifluoromethyl)phenyl)quinolin-8-amine (0.12 g, 0.391 mmol) was added. The mixture was stirred at room temperature for 18 hours before 10 mL water was added. The resulting precipitate was collected by filtration, and the solids were triturated in methanol to yield N-(2-(3-fluoro-5-(trifluoromethyl)phenyl)quinolin-8-yl)pyrazine-2-carboxamide as a beige solid (0.065 g, 31% yield). MS (ESI) calcd for C21H12F4N4O (m/z): 412.09. found: 413 [M+1].

Workup

  1. additionwas added
  2. additionwas added
  3. filtrationThe resulting precipitate was collected by filtration
  4. customthe solids were triturated in methanol

Sources & evidence

ORD record
ord-3a33903aa84e4341a5e971fcb0f64ffd
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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