Dimethylamine → HCID 12084978, compound

HRID 751428Notes

Reaction equation

HRID 751428 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:19](=[O:26])[CH2:20][C:21](OCC)=[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>[Cl:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:19](=[O:26])[CH2:20][C:21]([N:2]([CH3:3])[CH3:1])=[O:22])=[C:10]([C:15]([O:17][CH3:18])=[O:16])[N:11]2[CH3:14])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 21114499HCID 21114499, compound

Product 1

HCID 12084978HCID 12084978, 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 15 g (44.4 mmol) of ethyl 3-[6-chloro-2-(methoxycarbonyl)-1-methyl-1H-indol-3-yl]-3-oxo-propanoate, obtained in step 2.1., and 0.2 g (1.63 mmol) of 4-(N,N-dimethyl)aminopyridine in 100 ml of toluene. Immediately a condenser, surmounted by a balloon flask, is fitted and the solution is stirred at 100° C. under low pressure for 20 h. The mixture is cooled to ambient temperature and concentrated under reduced pressure and the residue is chromatographed on a silica gel column (eluent: cyclohexane/dichloromethane:50/50, then dichloromethane/ethyl acetate: 100/0 to 0/100). This gives 3.8 g of a yellow solid which is recrystallized from a dichloromethane/ethyl acetate mixture.

Workup

  1. customobtained in step 2.1
  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. customthe residue is chromatographed on a silica gel column (eluent
  7. customThis gives 3.8 g of a yellow solid which is recrystallized from a dichloromethane/ethyl acetate mixture

Sources & evidence

ORD record
ord-12f38167eca440b9a2588040847be0dd
Source dataset
uspto-grants-2008_07
Patent number
US07405306B2

Reaction notes

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