Methylamine → HCID 50943810, compound

HRID 400704Notes

Reaction equation

HRID 400704 reaction equation
[CH3:1][NH2:2].[CH3:3][N:4]1[CH2:32][CH2:31][C:7]2[N:8]([CH2:16][CH:17]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C:19]([O:21]CC)=O)[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1>O>[CH3:3][N:4]1[CH2:32][CH2:31][C:7]2[N:8]([CH2:16][CH:17]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C:19]([NH:2][CH3:1])=[O:21])[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 50943808HCID 50943808, compound

Product 1

HCID 50943810HCID 50943810, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Methylamine (1 mL) was added to ethyl 4-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-3-(4-fluorophenyl)butanoate (50 mg, 0.122 mmol) and the reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to RT, diluted with water (5 mL) and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was purified by silica gel chromatography (100-200 mesh) eluting with 0-7% MeOH-DCM as eluent.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by silica gel chromatography (100-200 mesh)
  6. washeluting with 0-7% MeOH-DCM as eluent

Sources & evidence

ORD record
ord-23b0979609f4472fac31a082ca1c4a5b
Source dataset
uspto-grants-2014_06
Patent number
US08741919B2

Reaction notes

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