Triethylamine → HCID 178504681, compound

HRID 2204784Notes

Reaction equation

HRID 2204784 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-8a198d7e41844cebb1f3b7d026546a7c
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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