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3-Amino-2-pyrazinecarboxylic acid → 3-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide

HRID 908379
Notes
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Reaction equation

HRID 908379 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5](C2C=NN(C3CCN(C(OC(C)(C)C)=O)CC3)C=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=2[N:12]=1.NC1C(C(O)=[O:44])=NC=CN=1.NC1C=CC(F)=CC=1O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[NH2:1][C:2]1[C:7]([C:8]([NH:12][C:11]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:10]=2[OH:9])=[O:44])=[N:6][CH:5]=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 726563-Amino-2-pyrazinecarboxylic acidHCID 1857632-Amino-5-fluorophenolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67387653Tert-butyl 4-[4-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 136374732
3-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The tert-butyl 4-[4-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]pyrazol-1-yl]piperidine-1-carboxylate used as starting material was prepared as follows: 3-aminopyrazine-2-carboxylic acid (5 g) and 2-amino-5-fluoro-phenol (5.94 g) were dissolved in DMF (30 ml). Triethylamine (5.81 g) and HATU (19.13 g) were added to the solution. The resulting mixture was stirred at room temperature for 24 hours, diluted with ethyl acetate (100 ml) and washed with brine (3×20 ml). The organic layer was dried over sodium sulfate. The precipitate was collected, recrystallized in ethanol and further purified by chromatography on silica gel (hexane/ethyl acetate/Methanol) to give 3-amino-N-(4-fluoro-2-hydroxy-phenyl)pyrazine-2-carboxamide (6 g). NMR Spectrum: (400 MHz, DMSOd6) 10.8 (s, 1H), 10.2 (s, 1H), 8.30 (m, 2H), 7.80 (s, 1H), 7.50 (br, 2H), 6.60 (m, 2H). Mass spectrum: M+H+ 249.

Workup

  1. customwas prepared
  2. washwashed with brine (3×20 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe precipitate was collected
  5. customrecrystallized in ethanol
  6. customfurther purified by chromatography on silica gel (hexane/ethyl acetate/Methanol)

Sources & evidence

ORD record
ord-9394b6aa5817401182d05fa1caa06630
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08017611B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes