Potassium Carbonate → HCID 66758476, compound

HRID 917106Notes

Reaction equation

HRID 917106 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:18]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:19][C:6]1=2.C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]2([C:44]#[N:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:33][CH:32]=1>O.C(#N)C.C(OCC)(=O)C>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([NH:37][C:38]2([C:44]#[N:45])[CH2:43][CH2:42][N:41]([CH2:2][CH2:3][CH:4]=[C:5]3[C:11]4[CH:12]=[CH:13][CH:14]=[N:15][C:10]=4[CH2:9][O:8][C:7]4[CH:16]=[CH:17][C:18]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:19][C:6]3=4)[CH2:40][CH2:39]2)=[CH:35][CH:36]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 23136852HCID 23136852, compoundHCID 666859992-[5-(3-Bromo-propylidene)-5,1 1-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol

Product 1

HCID 66758476HCID 66758476, compoundYield 8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

The title compound was prepared by dissolving 2-[5-(3-Bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (106.7 mg, 0.285 mmol) in water (4 ml) and acetonitrile (1 ml). To this was added potassium carbonate (82.7 mg, 0.599 mmol) and 4-(4-Chloro-phenylamino)-piperidine-4-carbonitrile (84.0 mg, 0.356 mmol). The reaction was heated to 50° C. and stirred overnight. The next day the reaction was allowed to cool to room temperature and diluted with ethyl acetate and water. The organic layer was washed twice with water, dried over magnesium sulfate, and concentrated under reduced pressure. The crude residue was purified by reverse phase HPLC to give the title compound (11.5 mg, 8% yield, 88% pure by LC/MS).

Workup

  1. customThe title compound was prepared
  2. temperatureto cool to room temperature
  3. washThe organic layer was washed twice with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-79b9beb5ef7b450a9dcb1578dcef1ee2
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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