Benzyl isocyanate → 3-amino-N-methyl-6-[3-({[(phenylmethyl)amino]carbonyl}amino)phenyl]pyrazine-2-carboxamide

HRID 646690Notes

Reaction equation

HRID 646690 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=2)=[CH:6][N:7]=1.[CH2:19]([N:26]=[C:27]=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[NH2:1][C:2]1[C:3]([C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:27]([NH:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:28])[CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 100374223-amino-6-(3-aminophenyl)-N-methylpyrazine-2-carboxamide

Product 1

HCID 686505323-amino-N-methyl-6-[3-({[(phenylmethyl)amino]carbonyl}amino)phenyl]pyrazine-2-carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-6-(3-aminophenyl)-N-methylpyrazine-2-carboxamide (0.25 g, 1.03 mmol) in dry tetrahydrofuran (2 mL) was added benzyl isocyanate (0.15 g, 1.12 mmol). The mixture was allowed to stir overnight. The solid product was filtered from the reaction mixture and triturated with hexane/ethyl acetate (9:1). The solid was collected by filtration and dried to afford 3-amino-N-methyl-6-[3-({[(phenylmethyl)amino]carbonyl}amino)phenyl]pyrazine-2-carboxamide (0.26 g, 70% yield) as light yellow solid. 1H NMR (400 MHz, d6-DMSO): 8.80 (m, 1H), 8.64 (s, 1H), 8.02 (s, 1H), 7.68 (d, 1H), 7.58 (d, 1H), 7.30 (m, 8H), 4.30 (d, 2H), 2.80 (d, 3H); MS (EI) for C20H20N6O2: 377 (MH+).

Workup

  1. filtrationThe solid product was filtered from the reaction mixture
  2. customtriturated with hexane/ethyl acetate (9:1)
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-4df6275a81374b0e81473cf4e392ca3d
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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