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

HRID 2192537Notes

Reaction equation

HRID 2192537 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:21]=3[CH:22]=[CH:23][N:24]=[C:25]4[CH2:30][CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])[N:16]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:13][CH2:12][CH:11]([F:14])[CH2:10]1)#[N:2]>Cl.O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:21]=3[CH:22]=[CH:23][N:24]=[C:25]4[CH2:30][CH2:31][C:32]([OH:34])=[O:33])[N:16]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:13][CH2:12][CH:11]([F:14])[CH2:10]1)#[N:2]

Participants

4

Reactant 1

HCID 581499051,1-Dimethylethyl 3-(5-{5-[3-cyano-4-(3-fluoro-1-pyrrolidinyl)phenyl]-1,2,4-oxadiazol-3-yl}-1-isoquinolinyl)propanoate

Product 1

HCID 444767703-(5-{5-[3-Cyano-4-(3-fluoro-1-pyrrolidinyl)phenyl]-1,2,4-oxadiazol-3-yl}-1-isoquinolinyl)propanoic acidYield 16.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 3-(5-{5-[3-cyano-4-(3-fluoro-1-pyrrolidinyl)phenyl]-1,2,4-oxadiazol-3-yl}-1-isoquinolinyl)propanoate (D51; 14 mg, 0.027 mmol) was stirred in 4M HCl in dioxane (1 ml) at room temperature for 7 hrs. The mixture was concentrated in a blow down unit and the residue was 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)) to give the title compound as a white solid (2 mg).

Workup

  1. concentrationThe mixture was concentrated in a blow down unit
  2. customthe residue was purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column
  3. washeluting with solvents A/B (A: Water+0.1% Formic acid, B

Sources & evidence

ORD record
ord-4a1440d82b76463fbcbea8ff4e8ef1e6
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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