Water → HCID 59536407, compound

HRID 445257Notes

Reaction equation

HRID 445257 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([CH2:36][C:37](Cl)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>C(Cl)Cl>[C:30]1([CH2:36][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 962WaterHCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536407HCID 59536407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (100 mg, 0.36 mmol, example 9 (step 3) and DIEA (62.8 μL, 0.36 mmol) in DCM (2 mL) was added phenylacetyl chloride (47.7 μL, 0.36 mmol). The resulting mixture was stirred at RT for 16 h. Then, H2O (3 mL) was added and the mixture was extracted with DCM (2×5 mL). The combined organic extracts were concentrated and the residue was dissolved in MeOH (1 mL). The solution mixture was purified by preparative HPLC (10-100% of MeCN (0.1% TFA)/H2O (0.1% TFA) to give the title compound as an off-white thick oil. MS (ESI, positive ion) m/z: 396 (M+H).

Workup

  1. extractionthe mixture was extracted with DCM (2×5 mL)
  2. concentrationThe combined organic extracts were concentrated
  3. dissolutionthe residue was dissolved in MeOH (1 mL)
  4. customThe solution mixture was purified by preparative HPLC (10-100% of MeCN (0.1% TFA)/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-e46eba027b59402ea36eb6ecbdfae1b2
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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