Triethylamine → HCID 59536267, compound

HRID 445375Notes

Reaction equation

HRID 445375 reaction equation
[I-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][CH2:19][O:20][CH3:21])[C:10](N2C=C[N+](C)=C2)=[O:11])=[CH:5][CH:4]=1.[F:22][C:23]([F:41])([F:40])[C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][CH2:32][NH:31]2)=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl>[F:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:18][CH2:19][O:20][CH3:21])[C:10]([N:31]2[CH2:32][CH2:33][C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:30]2[C:27]2[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:40])[F:41])=[CH:29][CH:28]=2)=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinolineHCID 86646595HCID 86646595, compound

Product 1

HCID 59536267HCID 59536267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a 50 mL round-bottomed flask was added 1-((4-fluorophenyl)(2-methoxy-ethyl)carbamoyl)-3-methyl-1H-imidazol-3-ium iodide (70 mg, 173 μmol, from step 3), (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (24 mg, 87 μmol), CH2Cl2 (1 mL), triethylamine (12 μL, 87 μmol). The reaction mixture was stirred at 40° C. for 28 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 30% EtOAc/hexanes to give (R)—N-(4-fluorophenyl)-N-(2-methoxyethyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide. MS (ESI pos. ion) m/z: 473 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-6c5cb11aa1894e8cb04c51a2ef9ca347
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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