Ammonia → 4-[5-[(Cyclopropylamino)carbonyl]-2-methylphenyl]-4,5-dihydro-5-oxo-6-[(phenylmethyl)amino]-2-pyrazinecarboxamide

HRID 337027Notes

Reaction equation

HRID 337027 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:6](=[O:22])[N:7]([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:12]([NH:14][CH:15]2[CH2:17][CH2:16]2)=[O:13])[CH:8]=1)#[N:2].N.[OH:32]O.O>CO>[CH:15]1([NH:14][C:12]([C:11]2[CH:18]=[CH:19][C:20]([CH3:21])=[C:9]([N:7]3[C:6](=[O:22])[C:5]([NH:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[N:4][C:3]([C:1]([NH2:2])=[O:32])=[CH:8]3)[CH:10]=2)=[O:13])[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 962WaterHCID 666864873-[5-Cyano-2-oxo-3-[(phenylmethyl)amino]-1(2H)-pyrazinyl]-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 666864354-[5-[(Cyclopropylamino)carbonyl]-2-methylphenyl]-4,5-dihydro-5-oxo-6-[(phenylmethyl)amino]-2-pyrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-[5-cyano-2-oxo-3-[(phenylmethyl)amino]-1(2H)-pyrazinyl]-N-cyclopropyl-4-methyl-benzamide (Example 104, 100 mg) in methanol (1 mL) was added conc. ammonia solution (1 mL) followed by 30% hydrogen peroxide solution (1 mL). After 12 h, water was added and the mixture was extracted with dichloromethane. The pooled organics were washed with brine, dried (MgSO4), filtered and the solvent removed. Purification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent) afforded the title compound (31 mg).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe pooled organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed
  6. customPurification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent)

Sources & evidence

ORD record
ord-ca80611a47d34cfc92e9be899bc2bdc7
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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