Methylamine → HCID 12073478, compound

HRID 749494Notes

Reaction equation

HRID 749494 reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:17]([C:18]([O:20]CC)=O)=[N:16][N:15]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[C:14](=[O:29])[C:9]=3[N:10]([CH3:13])[C:11]=2[CH:12]=1>ClCCl.CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:17]([C:18]([NH:2][CH3:1])=[O:20])=[N:16][N:15]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[C:14](=[O:29])[C:9]=3[N:10]([CH3:13])[C:11]=2[CH:12]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 21948037HCID 21948037, compound

Product 1

HCID 12073478HCID 12073478, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stream of gaseous methylamine is introduced into a solution of 0.28 g (0.76 mmol) of ethyl 7-fluoro-5-methyl-4-oxo-3-(pyridin-3-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate (obtained in stage 4.1.) in 30 ml of dichloromethane and 70 ml of methanol. Stirring is maintained for 4 h. The reaction medium is concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel (eluent: dichloromethane/methanol: 100/0 to 90/10). The solid obtained is recrystallized from a mixture of dichloromethane and ethyl acetate.

Workup

  1. temperatureis maintained for 4 h
  2. concentrationThe reaction medium is concentrated under reduced pressure
  3. customThe residue is purified by chromatography on a column of silica gel (eluent: dichloromethane/methanol: 100/0 to 90/10)
  4. customThe solid obtained
  5. customis recrystallized from a mixture of dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-d6e4969d645543e0933a74b36b4479af
Source dataset
uspto-grants-2008_07
Patent number
US07402682B2

Reaction notes

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