Hydrochloric Acid → 2-(4-Fluorobenzyl)-10-methoxy-4-(1-hydroxyethyl)-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494130Notes

Reaction equation

HRID 494130 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([O:23][CH3:24])=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[CH2:18][CH2:17][N:16]4[C:10]=3[C:9]([CH:25]=[O:26])=[N:8]2)=[CH:4][CH:3]=1.[CH3:29][Mg]Br.C(OCCCC)CCC.Cl>COCCOC.ClCCl>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([O:23][CH3:24])=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[CH2:18][CH2:17][N:16]4[C:10]=3[C:9]([CH:25]([OH:26])[CH3:29])=[N:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8909Butyl etherHCID 866248002-(4-Fluorobenzyl)-8-methyl-10-methoxy-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-4-carboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 688652402-(4-Fluorobenzyl)-10-methoxy-4-(1-hydroxyethyl)-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2-(4-fluorobenzyl)-8-methyl-10-methoxy-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-4-carboxaldehyde (42 mg, 0.11 mmol) in anhydrous DME (10 mL), a solution of methyl magnesium bromide in butyl ether (0.26 mL, 0.26 mmol; 1 M) was added. After stirring at room temperature for 5 minutes, the reaction mixture was treated with dilute hydrochloric acid, and diluted with dichloromethane. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound as yellow solid. ES MS M+1=401

Workup

  1. extractionThe organic extract
  2. washwas washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6b80db1d61604f87888245a5bbeadb0c
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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