Triethylamine → HCID 178504681, compound

HRID 78562Notes

Reaction equation

HRID 78562 reaction equation
[NH2:1][C:2]1[C:3]([C:18](O)=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.C(N(CC)CC)C.[NH2:38][C:39]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][C:40]=1[OH:46]>COCCOC.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:18]2[NH:38][C:39]3[C:40]([OH:46])=[CH:41][CH:42]=[CH:43][C:44]=3[N:45]=2)=[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 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 5799372,3-DiaminophenolHCID 51000409HCID 51000409, compound

Product 1

HCID 178504681HCID 178504681, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (120 mg, 0.4091 mmol), diethoxyphosphorylformonitrile (73.40 mg, 0.4500 mmol), triethylamine (124.2 mg, 171.1 μL, 1.227 mmol) and 2,3-diaminophenol (50.79 mg, 0.4091 mmol) in DME (5 mL) was heated in the microwave at 170° C. for 1 hour. The mixture was diluted with EtOAc, washed with water and brine and concentrated in vacuo The residue was then dissolved in DCM and triturated with ether to give the desired product as a yellow solid (115 mg, 74% Yield). 1H NMR (400 MHz, DMSO) 3.6 (3H, s), 6.65 (1H, d), 7.1-7.18 (2H, m), 8.0-8.1 (4H, m), 8.6 (2H, d), 8.9 (1H, s), 9.05 (1H, br s), 9.9 (1H, s), 12.9 (1H, b rs) ppm; MS (ES+) 382

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated in vacuo The residue
  3. dissolutionwas then dissolved in DCM
  4. customtriturated with ether

Sources & evidence

ORD record
ord-88572491691940b79f295afa78004cc3
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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