Dimethylamine → HCID 12084977, compound

HRID 2252714Notes

Reaction equation

HRID 2252714 reaction equation
[CH3:1][NH:2][CH3:3].[F:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:19](=[O:25])[CH2:20][C:21](OC)=[O:22])=[C:10]([C:15]([O:17][CH3:18])=[O:16])[N:11]2[CH3:14])=[CH:7][CH:6]=1>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:3])[C:21](=[O:22])[CH2:20][C:19]([C:9]1[C:8]2[C:12](=[CH:13][C:5]([F:4])=[CH:6][CH:7]=2)[N:11]([CH3:14])[C:10]=1[C:15]([O:17][CH3:18])=[O:16])=[O:25]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 12084976HCID 12084976, compound

Product 1

HCID 12084977HCID 12084977, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A stream of gaseous dimethylamine is passed into a mixture of 13 g (44.4 mmol) of methyl 3-[6-fluoro-2-(methoxycarbonyl)-1-methyl-1H-indol-3-yl]-3-oxo-propanoate, obtained in step 1.2., and 0.2 g (1.63 mmol) of 4-(N,N-dimethyl)aminopyridine in 80 ml of toluene. Immediately a condenser, surmounted by a balloon flask, is fitted and the solution is stirred at 100° C. for 20 h. The mixture is cooled to ambient temperature and concentrated under reduced pressure. 200 ml of dichloromethane, water and hydrochloric acid (1N) are added. The organic phase is separated off, washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a silica gel column (eluent: cyclohexane/dichloromethane: 50/50, then dichloromethane/ethyl acetate 100/0 to 0/100).

Workup

  1. customobtained in step 1.2
  2. customImmediately a condenser, surmounted by a balloon flask
  3. customis fitted
  4. temperatureThe mixture is cooled to ambient temperature
  5. concentrationconcentrated under reduced pressure
  6. addition200 ml of dichloromethane, water and hydrochloric acid (1N) are added
  7. customThe organic phase is separated off
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue is purified by chromatography on a silica gel column (eluent

Sources & evidence

ORD record
ord-9cde4270d80c4059a4be5914f563d0d1
Source dataset
uspto-grants-2008_01
Patent number
US07323467B2

Reaction notes

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