1,2,3,4-Tetrahydroisoquinoline → HCID 59170154, compound

HRID 1446324Notes

Reaction equation

HRID 1446324 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13](Cl)=[O:14])=[CH:4][CH:3]=1.[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][NH:17]1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([N:17]2[CH2:18][CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16]2)=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 729429065-(P-tolyl)isoxazole-4-carbonyl chloride

Product 1

HCID 59170154HCID 59170154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(4-methylphenyl)isoxazole-4-carbonyl chloride (10 mg, 0.045 mmol) in dichloromethane (1 mL) was added 1,2,3,4-tetrahydroisoquinoline (6.6 mg, 0.050 mmol, 1.1 eq), and the reaction mixture was stirred for 1 h. The solvent was removed, and the residue was purified by preparative reverse-phase HPLC to give the title compound. HRMS (ESI, pos. ion) m/z calcd for C20H18N2O2: 318.1368, found 318.1377.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-1098d1978d854f97bf948b153f05ef82
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

Loading…