Sodium Bicarbonate → 3-(2-Cyclopropylethylamino)-5-chloro-6-methyl-1-(benzyloxycarbonylmethyl)-pyrazinone

HRID 361377Notes

Reaction equation

HRID 361377 reaction equation
Cl.[CH:2]1([CH2:5][CH2:6][NH2:7])[CH2:4][CH2:3]1.[CH2:8]([O:15][C:16]([CH2:18][N:19]1[C:24]([CH3:25])=[C:23]([Cl:26])[N:22]=[C:21](Cl)[C:20]1=[O:28])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[CH:2]1([CH2:5][CH2:6][NH:7][C:21]2[C:20](=[O:28])[N:19]([CH2:18][C:16]([O:15][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:17])[C:24]([CH3:25])=[C:23]([Cl:26])[N:22]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 219160802-Cyclopropylethanamine hydrochloride

Product 1

HCID 542694253-(2-Cyclopropylethylamino)-5-chloro-6-methyl-1-(benzyloxycarbonylmethyl)-pyrazinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-cyclopropylethylamine hydrochloride (73 mg, 0.60 mmol), 1-benzyloxycarbonylmethyl-3,5-dichloro-6-methylpyrazinone (164 mg, 0.50 mmol) and sodium hydrogen carbonate (101 mg, 1.20 mmol) in toluene (1 mL) and water (0.5 mL) was stirred at 80° C. for 3 h. The reaction was then cooled and partitioned between methylene chloride and 10% citric acid solution. The organic layer was dried (Na2SO4) and evaporated in vacuo to give the title compound as a crystalline solid:

Workup

  1. temperatureThe reaction was then cooled
  2. custompartitioned between methylene chloride and 10% citric acid solution
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-99d4b3699ee9434bb6cc22a0691ee632
Source dataset
uspto-grants-1999_02
Patent number
US05866573

Reaction notes

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