Aniline → VE-821

HRID 522526Notes

Reaction equation

HRID 522526 reaction equation
[NH2:1][C:2]1[C:3]([C:18]([OH:20])=O)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.C(OP(C#N)(OCC)=O)C.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C>COCCOC.O>[NH2:1][C:2]1[C:3]([C:18]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:20])=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 51000409HCID 51000409, compound

Product 1

HCID 51000408VE-821Yield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.114 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 μL, 5.114 mmol), aniline (476.2 mg, 465.9 μL, 5.114 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) was stirred in DME (18.75 mL) at 120° C. for 18 hours. After this time water was added and the resultant solid collected by filtration and triturated with acetone to give the desired product (1.88 g, 71% Yield). 1H NMR (400.0 MHz, DMSO) δ 10.47 (s, 1H), 9.04 (s, 1H), 8.51 (d, J=8.4 Hz, 2H), 8.01 (d, J=8.4 Hz, 2H), 7.89 (s, 2H), 7.82 (d, J=7.9 Hz, 2H), 7.41 (t, J=7.8 Hz, 2H), 7.18 (t, J=7.3 Hz, 1H) and 3.28 (s, 3H) ppm; MS (ES+) 369.0.

Workup

  1. filtrationthe resultant solid collected by filtration
  2. customtriturated with acetone

Sources & evidence

ORD record
ord-3a7e3d18afeb418e83cfc9a6bfd3b8da
Source dataset
uspto-grants-2016_05
Patent number
US09334244B2

Reaction notes

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