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

HRID 2383329Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:10]1[CH:11]=[C:12]([C:20]2[O:24][N:23]=[C:22]([C:25]3[C:26]([CH3:48])=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]([CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])[N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)[N:21]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH:17]([CH3:19])[CH3:18])#[N:9]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:10]1[CH:11]=[C:12]([C:20]2[O:24][N:23]=[C:22]([C:25]3[C:26]([CH3:48])=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]([CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])[NH:30][CH2:29][CH2:28]4)[N:21]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH:17]([CH3:19])[CH3:18])#[N:9]

Participants

Conditions

Temperature: 25 °C

Procedure

Trifluoroacetic acid (1.0 ml, 13.0 mmol) was added dropwise at 25° C. under nitrogen to a solution of 4-(6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)butanoic acid (Preparation 32; 102 mg, 0.182 mmol) in dichloromethane (4.0 ml) and the resulting mixture was stirred at 25° C. for 1 h. The solvent was removed, and the residue co-evaporated with toluene followed by trituration with diethyl ether to give the title compound (76 mg) as a white solid.

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-43875f3202054fb6a211ba3436cfef40
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263620B2

Reaction notes

Loading…