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

HRID 2383326Notes

Reaction equation

HRID 2383326 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:45])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH:30]([CH2:34][C:35]([OH:37])=[O:36])[N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:45])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH:30]([CH2:34][C:35]([OH:37])=[O:36])[NH:29][CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59591087(6-(5-{3-Chloro-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 68733202[6-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl]acetic acid trifluoroacetateYield 58.7%

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-chloro-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 22; 75 mg, 0.138 mmol) in dichloromethane (3 ml) and the mixture was stirred at room temperature for 1 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 a pale brown solid (45 mg). Purification by MDAP gave the title compound (8.2 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-596e3f40a0754f22a573d78884a39f50
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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