Hydrochloric Acid → HCID 21183744, compound

HRID 1384828Notes

Reaction equation

HRID 1384828 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11](=[O:26])[N:12]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].Cl[CH2:30][O:31][CH3:32].Cl>CN(C)C=O.O1CCCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:30][O:31][CH3:32])[C:6]3[C:11](=[O:26])[N:12]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 135810259HCID 135810259, compound

Product 1

HCID 21183744HCID 21183744, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3.9 g (11 mmol) of ethyl 8-fluoro-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate in 200 ml of dimethylformamide is added to a suspension of 0.66 g (16 mmol) of sodium hydride in 100 ml of dimethylformamide. The mixture is stirred for 1.5 h at room temperature and a solution of 1.15 ml (14.3 mmol) of chloromethoxymethane in 10 ml of tetrahydrofuran is added. The mixture is stirred for 2 h, a solution of dilute hydrochloric acid is added and the precipitate is collected by filtration and dried under reduced pressure. 4.1 g (10.4 mmol) of solid are isolated, which solid is used as is in the following stage.

Workup

  1. stirringThe mixture is stirred for 2 h
  2. filtrationthe precipitate is collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-68417b067fb24e0b93f4a857c53bed93
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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