Methane → HCID 52937760, compound

HRID 78563

Reaction equation

HRID 78563 reaction equation
[NH2:1][C:2]1[C:3]([C:9](O)=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[C:12]1([NH2:19])[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=1.C(OP(C#N)(OCC)=O)C.C(N(CC)CC)C.C>COCCOC.CCOC(C)=O.O>[NH:18]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:19]=[C:9]1[C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([Br:8])[N:4]=1

Participants

9

Reactant 5

HCID 297MethaneHCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 52937760HCID 52937760, compoundYield 60.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (10 g, 45.87 mmol), benzene-1,2-diamine (5.45 g, 50.46 mmol), diethoxyphosphorylformonitrile (8.23 g, 50.46 mmol) and triethylamine (12.79 mL, 91.74 mmol) in DME (30 mL) was heated in the microwave at 170° C. for 40 minutes. The mixture was allowed to cool and water was added. The resultant dark-coloured precipitate was dissolved in EtOAc and stirred with charcoal for 30 minutes. After filtering through celite, the filtrate was concentrated in vacuo to give the product as a yellow solid (8.04 g, 60% Yield). 1H NMR (400 MHz, DMSO) 7.22-7.32 (2H, m), 7.55 (1H, d), 7.75 (1H, d), 7.8 (1 h, br s), 8.8 (1H, br s), 13.1 (1H, s); MS (ES+) 291

Workup

  1. temperatureto cool
  2. filtrationAfter filtering through celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3098fade2ad445e28fe562e67f568c00
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Linked notes

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