Acetic Acid → 4'-Trifluoromethylbiphenyl-2-carboxylic acid-[2-(2-pyridin-2-yl-ethyl)-1,2,3,4-tetrahydroisoquinolin-6-yl]-amide

HRID 1954431Notes

Reaction equation

HRID 1954431 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)=[CH2:31].C(O)(=O)C>CO>[N:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:30][CH2:31][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:6]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75212-VinylpyridineHCID 110147584'-Trifluoromethyl-biphenyl-2-carboxylic acid (1,2,3,4tetrahydroisoquinolin-6-yl)-amide

Product 1

HCID 232962034'-Trifluoromethylbiphenyl-2-carboxylic acid-[2-(2-pyridin-2-yl-ethyl)-1,2,3,4-tetrahydroisoquinolin-6-yl]-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound (II) (300 mg, 0.76 mmole), 2-vinylpyridine (95 mg, 0.91 mmole) and glacial acetic acid (24 mg, 0.40 mmole) were combined in 15 mL of methanol and heated to reflux for 24 hrs. The solvent was removed under vacuum and the residue was purified using silica gel chromatography with a gradient of 0 to 3% methanol in ethyl acetate as the eluent.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hrs
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified

Sources & evidence

ORD record
ord-9286317a76da4a1187500e3327d4f032
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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