2-Pyrazinecarboxylic acid → HCID 136359923, compound

HRID 520442Notes

Reaction equation

HRID 520442 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N: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)[NH:8][C:7]2=[O:22].[N:23]1[CH:28]=[CH:27]N=[CH:25][C:24]=1[C:29]([OH:31])=O.[CH3:32]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CC(N(C)C)=O.O>[O:22]=[C:7]1[C:6]2[C:11](=[C:2]([NH:1][C:29](=[O:31])[C:24]3[CH:25]=[CH:32][CH:27]=[CH:28][N:23]=3)[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[NH:8]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 136127578HCID 136127578, compound

Product 1

HCID 136359923HCID 136359923, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 8-amino-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one 9 (125 mg, 0.41 mmol), pyrazine-2-carboxylic acid 10 (102 mg, 0.82 mmol), HATU (342 mg, 0.90 mmo) and DIPEA (214 μl, 1.2 mmol) in DMAC (5 mL) were heated at 70° C. for 12 h then poured into H2O. The precipitate was collected by filtration, rinsed with H2O then recrystallized from EtOH to give Compound 231 (144 mg, 86% yield) as a white solid. MS (ESI) calc. for C20H12F3N5O2: 411.09. found: 412 [M+H].

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washrinsed with H2O
  3. customthen recrystallized from EtOH

Sources & evidence

ORD record
ord-c75740068de84870a1c5b7700c77b4c4
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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