Trifluoroacetic acid → 3-(5-methyl-4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinoline

HRID 1270818Notes

Reaction equation

HRID 1270818 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH:24]([C:25]2[NH:26][C:27]([CH3:36])=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:29]=2)[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)=O)(C)(C)C>>[CH3:36][C:27]1[NH:26][C:25]([CH:24]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][NH:15]2)=[N:29][C:28]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23570722HCID 23570722, compound

Product 1

HCID 219141423-(5-methyl-4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinoline

Procedure

To a solution of TFA (5 mL) cooled to about 0° C. was added the compound prepared in Step A above (1.10 g, 2.82 mmol), and the reaction mixture stirred for about 30 minutes. The reaction mixture was then removed from the ice bath and allowed to warm to room temperature. Excess TFA was removed under a stream of N2. The residue was partitioned between saturated NaHCO3 and dichloromethane. The aqueous phase was washed with a second portion of dichloromethane and the organic phases combined. The combined organic phase was dried over Na2SO4, then filtered to yield the title product as a solution in dichloromethane, which was used without further purification or isolation.

Workup

  1. customThe reaction mixture was then removed from the ice bath
  2. customExcess TFA was removed under a stream of N2
  3. customThe residue was partitioned between saturated NaHCO3 and dichloromethane
  4. washThe aqueous phase was washed with a second portion of dichloromethane
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-15f1383959394cefa5c45177b28985ff
Source dataset
uspto-grants-2007_04
Patent number
US07202381B2

Reaction notes

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