Sodium Hydroxide → HCID 44476772, compound

HRID 2192539Notes

Reaction equation

HRID 2192539 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([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][CH2:31][C:32]([O:34]CC)=[O:33])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]>C(O)(C)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([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][CH2:31][C:32]([OH:34])=[O:33])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58149913HCID 58149913, compound

Product 1

HCID 44476772HCID 44476772, compoundYield 15.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydroxide (16 mg) was added to a suspension of ethyl 4-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]butanoate (D41; 0.1 g) in isopropanol (10 ml) and water (10 ml). The reaction mixture was heated to 70° C. for 2 hours. After cooling, isopropanol was evaporated in vacuo and the remaining aqueous solution was acidified with aq. HCl (0.5 N) to pH=1. The aqueous solution was extracted with DCM (2×20 ml). The organic fractions were combined and dried over anhydrous sodium sulphate. The dried solution was filtered and the filtrate was concentrated. The residue was washed with THF (3×10 ml) to afford the title compound (15 mg). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 2.04 (2H, m), 2.40 (2H, m), 3.34 (2H, m), 4.89 (1H, m), 7.47 (1H, d), 7.88 (1H, dd), 8.17 (1H, dd), 8.24 (1H, d), 8.57 (4H, m), 12.11 (1H, s).

Workup

  1. temperatureAfter cooling
  2. customisopropanol was evaporated in vacuo
  3. extractionThe aqueous solution was extracted with DCM (2×20 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationThe dried solution was filtered
  6. concentrationthe filtrate was concentrated
  7. washThe residue was washed with THF (3×10 ml)

Sources & evidence

ORD record
ord-57f6a5ad9515437786d7ce4dbadcbddd
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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