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

HRID 2192533Notes

Reaction equation

HRID 2192533 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[CH2:13][CH2:12]1)#[N:2]>Cl.O1CCOCC1.CN1CCCC1=O>[C:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[CH2:13][CH2:12]1)#[N:2]

Participants

5

Reactant 1

HCID 668773731,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate

Product 1

HCID 444766733-[5-(5-{3-Cyano-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acidYield 33.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate (D48; 36 mg, 0.072 mmol) was dissolved in 4N HCl in 1,4-dioxane (4 ml) and the mixture was allowed to stand at room temperature for 4.5 h. The solvent was evaporated in vacuo and the residue triturated with dry ether to give a white solid which was dissolved in N-methyl-2-pyrrolidinone (1 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 dried under a stream of nitrogen to give the title compound as a white solid (10.5 mg)

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue triturated with dry ether
  3. customto give a white solid which
  4. custompurified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column
  5. washeluting with solvents A/B (A: Water+0.1% Formic acid, B
  6. customThe solvent was dried under a stream of nitrogen

Sources & evidence

ORD record
ord-95350a07e7b243f4bd751b74783c9c5c
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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