1,1-Dimethylethyl 3-[5-(5-{3-chloro-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate → 3-[5-(5-{3-Chloro-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acid hydrochloride

HRID 2192532Notes

Reaction equation

HRID 2192532 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:20]=3[CH:21]=[CH:22][N:23]=[C:24]4[CH2:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11]>Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:20]=3[CH:21]=[CH:22][N:23]=[C:24]4[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:13])[F:11]

Participants

4

Reactant 1

HCID 581499241,1-Dimethylethyl 3-[5-(5-{3-chloro-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate

Product 1

HCID 668997993-[5-(5-{3-Chloro-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acid hydrochlorideYield 124.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 3-[5-(5-{3-chloro-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate (D47; 55 mg, 0.103 mmol) was dissolved in 4N HCl in 1,4-dioxane (4 ml) and the solution allowed to stand at room temperature for 2 h. A white precipitate was formed which was filtered off, washed with dry ether and dried to give the title compound as a white solid (33 mg)

Workup

  1. customA white precipitate was formed which
  2. filtrationwas filtered off
  3. washwashed with dry ether
  4. customdried

Sources & evidence

ORD record
ord-7a60e1321121478ebf7f83a9ef88b540
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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