Water → N-(4-Fluorophenyl)-3-methyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445246Notes

Reaction equation

HRID 445246 reaction equation
Cl.[CH3:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[NH:4]1.CCN(C(C)C)C(C)C.[F:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]=[C:40]=[O:41])=[CH:35][CH:34]=1.O>C(Cl)Cl>[F:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([N:4]2[CH:3]([CH3:2])[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]2[C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:17][CH:18]=2)=[O:41])=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 709554-Fluorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 68496449HCID 68496449, compound

Product 1

HCID 59536362N-(4-Fluorophenyl)-3-methyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrogen chloride (370 mg, 1.27 mmol) and DIEA (1.1 mL, 6.35 mmol) in DCM (5 mL) was added 4-fluorophenyl isocyanate (143 μL, 1.27 mmol). The mixture was then stirred at RT for 0.5 h. Water (10 mL) was added and the mixture was extracted with DCM (2×15 mL). The combined organic extracts were dried over MgSO4 and concentrated to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 429 (M+H).

Workup

  1. extractionthe mixture was extracted with DCM (2×15 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c9506b10695f4c41a26ed17a61cd0d6e
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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