Methanol → HCID 42634733, compound

HRID 445256Notes

Reaction equation

HRID 445256 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:30]1([N:36]=[C:37]=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CO>C(Cl)Cl>[C:30]1([NH:36][C:37]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=2)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 42634733HCID 42634733, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (500 mg, 1.80 mmol) and DIEA (0.314 mL, 1.80 mmol) in DCM (9 mL) was added phenyl isocyanate (0.196 mL, 1.80 mmol). The resulting mixture was stirred at RT for 3 h. Then, MeOH (50 mL) was added and the mixture was concentrated. The residue was purified by silica gel flash column chromatography (0%-50% EtOAc/hexane) to give the title compound as a light yellow solid. The solid was then washed with MeOH (3×20 mL) to give 440 mg of the title compound as a white solid. MS (ESI, positive ion) m/z: 397 (M+H).

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by silica gel flash column chromatography (0%-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-2edc8794e46f4a889575089e9accf077
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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