Triethylamine → Ethyl 2-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinyl)-2-oxoacetate

HRID 2204874

Reaction equation

HRID 2204874 reaction equation
[NH2:1][C:2]1[C:3]([C:20]([NH:22][NH2:23])=[O:21])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.CCN(CC)CC.Cl[C:32](=[O:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34]>C1COCC1>[NH2:1][C:2]1[C:3]([C:20]([NH:22][NH:23][C:32](=[O:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:21])=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:15])=[O:16])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 594716323-Amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbohydrazide

Product 1

HCID 59472330Ethyl 2-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinyl)-2-oxoacetateYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbohydrazide (2 g, 5.963 mmol) and Et3N (1.810 g, 2.493 mL, 17.89 mmol) were dissolved in THF (128.0 mL) and treated dropwise with ethyl 2-chloro-2-oxo-acetate (814.2 mg, 666.3 μL, 5.963 mmol) at 0° C. The reaction mixture was warmed slowly to room temperature and stirred for 1.5 h. The reaction mixture was filtered and grey solid washed with THF. The filtrate was evaporated to dryness azeotroping with acetonitrile. Then residue was then triturated with acetonitrile to give the product as a yellow solid (1.52 g, 58%); 1H NMR (400 MHZ, DMSO) d 1.19 (m, 6H), 1.32 (m, 3H), 3.34 (m, 1H), 4.32 (m, 2H), 7.88 (m, 2H), 8.56 (m, 2H), 9.07 (s, 1H), 10.95 (s, 1H) and 11.05 (s, 1H) ppm; MS (ES+) 436.32

Workup

  1. filtrationThe reaction mixture was filtered
  2. washgrey solid washed with THF
  3. customThe filtrate was evaporated to dryness
  4. customazeotroping with acetonitrile
  5. customThen residue was then triturated with acetonitrile

Sources & evidence

ORD record
ord-1b5134440e5448998c7d43450c83ad60
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Linked notes

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