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

HRID 2383327Notes

Reaction equation

HRID 2383327 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]([CH3:46])=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]([CH2:35][C:36]([OH:38])=[O:37])[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]([CH3:46])=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]([CH2:35][C:36]([OH:38])=[O:37])[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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59591092(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)acetic acid

Product 1

HCID 68773060[6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl]acetic acid trifluoroacetateYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.0 ml, 13.0 mmol) was added dropwise at 25° C. under nitrogen to a solution of (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)acetic acid (Preparation 23; 42 mg, 0.079 mmol) in dichloromethane (3.0 ml) and the mixture was stirred at room temperature for ca. 2 h. The solvent was removed in vacuo and the residue co-evaporated with toluene, dried for 20 min under vacuum then triturated with diethyl ether to give the title compound (20 mg) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dry with materialthe residue co-evaporated with toluene, dried for 20 min under vacuum
  3. customthen triturated with diethyl ether

Sources & evidence

ORD record
ord-a36795cf153e46599f91fbb70a449798
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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