Methane → HCID 178508343, compound

HRID 646735Notes

Reaction equation

HRID 646735 reaction equation
[NH2:1][C:2]1[C:3]([C:16]#[N:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=2)=[CH:6][N:7]=1.[C:18]([NH:26][NH2:27])(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C=O)C.C>CCOC(C)=O.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[N:4][C:3]=1[C:16]1[NH:17][C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:26][N:27]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 6228DimethylformamideHCID 11955BenzoylhydrazineHCID 587105723-Amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile

Product 1

HCID 178508343HCID 178508343, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 3-amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile (0.11 g, 0.5 mmol) and benzoic hydrazide (0.15 g, 1 mmol) were heated at 180-200° C. for 30 min. After cooling, the reaction mass was taken up with 5 mL DMF and the obtained solution was diluted with EtOAc and water, clarified with charcoal and filtered on Celite. The organic layer was separated. After drying over sodium sulfate, the ethyl acetate was evaporated under reduced pressure. Purification of the residue by preparative HPLC (Acetonitrile/water) gave desired product (50 mg): 1H NMR (400 MHz; DMSO-d6): 8.3 (s, 1H); 8.1 (m, 2H); 7.6-7.3 (m, 7H); 5.45 (t, 1H); 4.6 (d, 2H); MS (EI) for C23H22N5OF3 HCl: 442 (MH+).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered on Celite
  3. customThe organic layer was separated
  4. dry with materialAfter drying over sodium sulfate
  5. customthe ethyl acetate was evaporated under reduced pressure
  6. customPurification of the residue by preparative HPLC (Acetonitrile/water)

Sources & evidence

ORD record
ord-1d31dba7f196450bbc106bb2d5fa2cc2
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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