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

HRID 2192530Notes

Reaction equation

HRID 2192530 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH:20]=[CH:21][N:22]=[C:23]4[CH2:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH:20]=[CH:21][N:22]=[C:23]4[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 581499031,1-Dimethylethyl 3-[5-(5-{3-chloro-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate

Product 1

HCID 444765803-[5-(5-{3-Chloro-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acidYield 77.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl 3-[5-(5-{3-chloro-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate (D45; 22 mg, 0.043 mmol) in 4N HCl in 1,4-dioxane (4 ml) was allowed to stand at room temperature for 2 h. The solvent was evaporated to give a white solid, which was triturated with dry ether to give a white solid (15 mg). The sample was dissolved in NMP (0.5 ml) and purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column, eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid)). The solvent was evaporated in vacuo to give the title compound (5 mg).

Workup

  1. customThe solvent was evaporated
  2. customto give a white solid, which
  3. customwas triturated with dry ether

Sources & evidence

ORD record
ord-2f1ec89febc04a97bb0c5cf5563338f6
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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