Potassium Carbonate → HCID 59190882, compound

HRID 418339Notes

Reaction equation

HRID 418339 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:28])[NH:17][C:18]2[CH:27]=[C:26]3[C:21]([CH2:22][CH2:23][NH:24][CH2:25]3)=[CH:20][CH:19]=2)[CH:11]=1)=[O:7].Br[CH2:35][CH:36]([F:38])[F:37].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:37][CH:36]([F:38])[CH2:35][N:24]1[CH2:23][CH2:22][C:21]2[C:26](=[CH:27][C:18]([NH:17][C:16]([C:12]3[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=3)[CH2:9][NH:8][C:6](=[O:7])[C:5]3[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:28])=[CH:19][CH:20]=2)[CH2:25]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1361862-Bromo-1,1-difluoroethaneHCID 25057409Benzamide, 3,4-dimethoxy-N-[[3-[[(1,2,3,4-tetrahydro-7-isoquinolinyl)amino]carbonyl]phenyl]methyl]-

Product 1

HCID 59190882HCID 59190882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved 3,4-dimethoxy-N-[3-(1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide (50.0 mg, 0.12 mmol) in 1 mL of DMF. Added 2-bromo-1,1-difluoro-ethane and (0.02 mL, 0.20 mmol) K2CO3 (50.0 mg, 0.36 mmol). The mixture was stirred at room temperature overnight. LC-MS indicated low conversion to alkylated product. Heated the mixture to 60° C. for 8 h with continued low conversion, thereafter it was heated to 75° C. for 48 h. LC-MS indicated the desired product. Dissolved in 5 mL of DMF and purified via prep HPLC (5%-95% CH3CN/H2O) to give 28.1 mg of N-{3-[2-(2,2-difluoro-ethyl)-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl]-benzyl}-3,4-dimethoxy-benzamide. MS, electrospray 510.4 (M+H).

Workup

  1. temperatureHeated the mixture to 60° C. for 8 h with continued low conversion
  2. temperatureit was heated to 75° C. for 48 h

Sources & evidence

ORD record
ord-f9c8408c3e4b47058f0c90d5bfc02236
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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