Ethyl Acetate → 4'-Trifluoromethylbiphenyl-2-carboxylic acid-[2-(thiophen-2-yl-acetyl)-1,2,3,4-tetrahydroisoquinolin-6-yl]-amide

HRID 1954432Notes

Reaction equation

HRID 1954432 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.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36](O)=[O:37].Cl.CN(C)CCCN=C=NCC.C(OCC)(=O)C>C(Cl)Cl>[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36]([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)=[O:37]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159702-Thiopheneacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110147584'-Trifluoromethyl-biphenyl-2-carboxylic acid (1,2,3,4tetrahydroisoquinolin-6-yl)-amide

Product 1

HCID 102082054'-Trifluoromethylbiphenyl-2-carboxylic acid-[2-(thiophen-2-yl-acetyl)-1,2,3,4-tetrahydroisoquinolin-6-yl]-amideYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound (II) (3.1 g, 7.8 mmole), 2-thiopheneacetic acid (1.14 g, 8.0 mmole) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.7 g, 8.8 mmole) were stirred in 50 mL of methylene chloride for 12 hrs. at ambient temperature. The reaction was diluted with methylene chloride, washed with 1N hydrochloric acid, 1N NaOH, water and brine. Purification of the residue obtained on evaporation was accomplished with silica gel chromatography using 50% ethyl acetate in hexanes as the eluent to yield 3.6 g of the title compound as a solid.

Workup

  1. customat ambient temperature
  2. washwashed with 1N hydrochloric acid, 1N NaOH, water and brine
  3. customPurification of the residue
  4. customobtained on evaporation

Sources & evidence

ORD record
ord-269a88ba0c3947dd987cb86753b055f6
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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