Water → HCID 59536310, compound

HRID 445268Notes

Reaction equation

HRID 445268 reaction equation
[C:1]1([NH:7][C:8]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:33].O>C1COCC1>[CH3:33][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]1[C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 42634733HCID 42634733, compound

Product 1

HCID 59536310HCID 59536310, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-phenyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (100 mg, 0.252 mmol, example 9 (step 3) in THF (1 mL) was added sodium hydride (12 mg, 0.505 mmol) slowly. The resulting mixture was stirred at RT for 15 min and iodomethane (16 μL, 0.252 mmol) was added. The mixture was stirred at RT for 16 h. Then, H2O (2 mL) was added and the mixture was extracted with EtOAc (2×2 mL). The combined organic extracted were dried over MgSO4 and concentrated. The residue was then dissolved in DMSO (1 mL) and the solution mixture was purified by preparative HPLC (10%-400% of MeCN (0.1% TFA)/H2O (0.1% TFA) to give the title compound as an off-white solid. MS (ESI, positive ion) m/z: 411 (M+H).

Workup

  1. stirringThe mixture was stirred at RT for 16 h
  2. extractionthe mixture was extracted with EtOAc (2×2 mL)
  3. extractionThe combined organic extracted
  4. dry with materialwere dried over MgSO4
  5. concentrationconcentrated
  6. dissolutionThe residue was then dissolved in DMSO (1 mL)
  7. customthe solution mixture was purified by preparative HPLC (10%-400% of MeCN (0.1% TFA)/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-d959545b9b1c4629afb5a32358e03896
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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