Dichloromethane → (R)-1-(4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445347Notes

Reaction equation

HRID 445347 reaction equation
[F:1][C:2]([F:7])([F:6])[C@@H:3]([NH2:5])[CH3:4].C(Cl)Cl.N1([C:16](N2C=CN=C2)=[O:17])C=CN=C1.[F:23][C:24]([F:42])([F:41])[C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34][CH2:33][NH:32]2)=[CH:27][CH:26]=1>C1COCC1>[F:42][C:24]([F:23])([F:41])[C:25]1[CH:26]=[CH:27][C:28]([C@@H:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34][CH2:33][N:32]2[C:16]([NH:5][C@@H:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[O:17])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 10964447(S)-1,1,1-trifluoropropan-2-amineHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536364(R)-1-(4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1,1,1-trifluoropropan-2-amine (90.9 μl, 884 μmol) in 4:1 CH2Cl2:THF (5 mL) is added di(1H-imidazol-1-yl)methanone (215 mg, 1326 μmol) and the flask was sealed and stirred at room temperature for 1.5 h. (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (307 mg, 1105 μmol) was added and the reaction stirred at 2 h. The reaction was directly purified by reverse phase HPLC to give (R)-1-(4-(trifluoromethyl)phenyl)-N—((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide as a white powder. MS (ESI pos. ion) m/z: 417 (M+1).

Workup

  1. customthe flask was sealed
  2. additionwas added
  3. customThe reaction was directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-59fb578bf90c4d3b95c357639152a83d
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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