Trifluoroacetic acid → HCID 11179414, compound

HRID 2374446Notes

Reaction equation

HRID 2374446 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]3[O:23][N:22]=[C:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[C:26]([C:36]([F:39])([F:38])[F:37])[CH:25]=4)[N:20]=3)[CH:15]=2)[CH2:10]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:39][C:36]([F:37])([F:38])[C:26]1[CH:25]=[C:24]([C:21]2[N:20]=[C:19]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[CH2:10][N:9]([CH2:8][CH2:7][C:6]([OH:40])=[O:5])[CH2:18][CH2:17]4)[O:23][N:22]=2)[CH:29]=[CH:28][C:27]=1[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69171997HCID 69171997, compound

Product 1

HCID 11179414HCID 11179414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 3-{6-[3-(2-trifluoromethyl-biphenyl-4-yl)-[1,2,4]oxadiazol-5-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propionic acid tert-butyl ester in CH2Cl2 (1 mL) is added TFA(1 mL). The mixture is stirred at room temperature for an hour. All the solvents are evaporated. The mixture is purified by reverse phase preparative LC/MS to give 3-{6-[3-(2-Trifluoromethyl-biphenyl-4-yl)-[1,2,4]oxadiazol-5-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propionic acid: 1H NMR (DMSO, 400 MHz) δ 8.52 (s, 1H), 8.38 (d, 1H), 8.15 (s, 1H), 8.10 (d, 1H), 7.68 (d, 1H), 7.50 (m, 4H), 7.38 (m, 2H), 3.20-3.50 (m, 8H), 2.92 (t, 2H), MS (ES+): (494.10, M+1)+.

Workup

  1. customAll the solvents are evaporated
  2. customThe mixture is purified by reverse phase preparative LC/MS

Sources & evidence

ORD record
ord-ce5d7b4d1a0c48e29a9ace9426d162ab
Source dataset
uspto-grants-2008_12
Patent number
US07462629B2

Reaction notes

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