Water → HCID 68651120, compound

HRID 646755Notes

Reaction equation

HRID 646755 reaction equation
CNC(C1C(N)=NC=C(C2C=CC=C(CN)C=2)N=1)=O.[NH2:20][C:21]1[C:22]([C:43]([NH:45][CH3:46])=[O:44])=[N:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][NH:34][C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:36])[CH:28]=2)=[CH:25][N:26]=1.C(Cl)(=O)C1C=CC=CC=1.O>C(#N)C>[CH3:46][NH:45][C:43]([C:22]1[C:21]([NH2:20])=[N:26][CH:25]=[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][NH:34][C:35](=[O:36])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:28]=2)[N:23]=1)=[O:44]

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 68651368HCID 68651368, compound

Product 1

HCID 68651120HCID 68651120, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Amino-N-methyl-6-(3-{[(phenylcarbonyl)amino]methyl}phenyl)pyrazine-2-carboxamide 3-Amino-6-(3-aminomethyl-phenyl)-pyrazine-2-carboxylic acid methylamide (10.0 mg, 0.04 mmol) was dissolved in acetonitrile (2 mL) followed by the addition of TEA (11.2 μl, 0.08 mmol) and benzoyl chloride (3.50 μl, 0.04 mmol). It was stirred at room temperature overnight. The reaction mixture was poured into water (10 mL), and extracted with ethyl acetate (2×10 mL) then dried over anhydrous sodium sulfate and filteration, concentration and purified by column chromatography (50% Ethylacetae/hexanes) to give 3-amino-6-[3-(benzoylamino-methyl)-phenyl]-pyrazine-2-carboxylic acid methylamide, 8.70 mg (85.0% yield): 1H NMR (400 MHz, CDCl3): δ 8.60 (s, 1H), 8.00 (br, 1H), 7.80 (m, 4H), 7.52 (m, 4H), 7.20 (s, 1H), 6.50 (br, 1H), 4.80 (m, 2H), 3.00 (d, 3H); MS (EI) for C20H19N5O2: 362.41 (MH+).

Workup

  1. extractionextracted with ethyl acetate (2×10 mL)
  2. dry with materialthen dried over anhydrous sodium sulfate and filteration, concentration
  3. custompurified by column chromatography (50% Ethylacetae/hexanes)

Sources & evidence

ORD record
ord-82598c221e1747878f6c56a04806dea5
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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