(4-Fluorobenzyl)hydrazine → 10-(Benzyloxy)-2-(4-fluorobenzyl)-4,8-dimethyl-7,8-dihydropyrazino-[1',2':1,5]pyrrolo-[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494094Notes

Reaction equation

HRID 494094 reaction equation
[C:1]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[C:12](=[O:13])[C:7]2=[C:6]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1[C:23](OCC)=[O:24])(=O)[CH3:2].[F:28][C:29]1[CH:37]=[CH:36][C:32]([CH2:33][NH:34][NH2:35])=[CH:31][CH:30]=1>C(O)(=O)C.C1(C)C=CC=CC=1>[CH2:16]([O:15][C:6]1[C:5]2[C:23](=[O:24])[N:34]([CH2:33][C:32]3[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=3)[N:35]=[C:1]([CH3:2])[C:4]=2[N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[C:12](=[O:13])[C:7]=12)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 15163346(4-Fluorobenzyl)hydrazineHCID 68866335Ethyl 6-acetyl-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate

Product 1

HCID 6886362910-(Benzyloxy)-2-(4-fluorobenzyl)-4,8-dimethyl-7,8-dihydropyrazino-[1',2':1,5]pyrrolo-[2,3-d]pyridazine-1,9(2H,6H)-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 6-acetyl-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate (65 mg, 0.18 mmol) and 4-fluorobenzyl hydrazine (0.12 g, 0.88 mmol), and acetic acid (3 drops) in toluene (40 mL) was heated in a sealed tube at 120° C. overnight. The reaction mixture was concentrated under vacuum, and the residue was subjected to column chromatography on silica gel eluted with 1-5% methanol in ethyl acetate gradient to provide titled product.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. washeluted with 1-5% methanol in ethyl acetate gradient

Sources & evidence

ORD record
ord-bfa871f64c044224a725d43f597742d0
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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