Trifluoroacetic acid → HCID 19601674, compound

HRID 610653Notes

Reaction equation

HRID 610653 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([N:20]([CH3:44])[CH2:21][CH2:22][CH2:23][O:24]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:19])[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([N:20]([CH3:44])[CH2:21][CH2:22][CH2:23][OH:24])=[O:19])[N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19601668HCID 19601668, compound

Product 1

HCID 19601674HCID 19601674, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-iodophenyl)-N-methyl-N-(3-triphenylmethoxy-propyl)-3-isoquinolinecarboxamide (107 mg, 0.16 mmol) in CH2Cl2 (10 mL) was added dropwise TFA (1 mL). The mixture was stirred at room temperature for 40 min. Then it was transferred into a separatory funnel and washed with saturated NaHCO3 solution (2×10 mL), water (20 mL), and brine (20 mL), then dried (MgSO4), and filtered. After removing the solvent in vacuo, the residue was purified on column (silica gel, 2% MeOH/CH2Cl2, 0.1% Et3N), thereby affording starting material (5.2 mg) and the titled compound (51.2 mg, 73%). mp 51-52° C. 1H NMR (CDCl3) d 1.78-1.95 (m, 2 H, CH2), 3.12, 3.19 (two s, total 3 H, N--Me), 3.52-3.74 (m, 3 H), 3.82-4.32 (m, 2 H), 7.19-7.31 (m, 1 H, aromatic), 7.35-7.42 (m, 1 H, aromatic), 7.48-7.63 (m, 3 H, aromatic), 7.72-7.81 (m, 2 H, aromatic), 8.17, 8.26 (two s, total 1 H, aromatic). HRMS Cacld. for C20H19IN2O: 446.0491. Found: 446.0501.

Workup

  1. customThen it was transferred into a separatory funnel
  2. washwashed with saturated NaHCO3 solution (2×10 mL), water (20 mL), and brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified on column (silica gel, 2% MeOH/CH2Cl2, 0.1% Et3N)
  7. customaffording

Sources & evidence

ORD record
ord-491d2fb4f1d84c6a87b28257f842c44a
Source dataset
uspto-grants-1999_12
Patent number
US05998624

Reaction notes

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