Trifluoroacetic acid → 6-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydroisoquinoline trifluoroacetate

HRID 2059952Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:18]([CH3:34])=[C:19]4[C:24](=[CH:25][CH:26]=3)[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>ClCCl>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:18]([CH3:34])=[C:19]4[C:24](=[CH:25][CH:26]=3)[CH2:23][NH:22][CH2:21][CH2:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1,1-dimethylethyl 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 19; 210 mg; 0.434 mmol) in dichloromethane (3 ml) at 0° C. was added trifluoroacetic acid (3 ml) dropwise. The resulting mixture was stirred at 0° C. for 1 h, giving a pale yellow solution. Removal of the solvent and co-evaporation with toluene gave a white solid, which was triturated with diethyl ether to give the title compound as a white solid (206 mg).

Workup

customgiving a pale yellow solution
customRemoval of the solvent and co-evaporation with toluene
customgave a white solid, which
customwas triturated with diethyl ether

Sources & evidence

ORD record: ord-958d35858bec4c8f8f4bf5574d021bbb
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278324B2

Reaction notes

Loading…