Sodium Hydroxide → HCID 44476771, compound

HRID 2192538Notes

Reaction equation

HRID 2192538 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]=[N: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]=[N:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58149876HCID 58149876, compound

Product 1

HCID 44476771HCID 44476771, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydroxide (50 mg) was added to a suspension of ethyl 4-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]butanoate (D44; 0.36 g) in isopropanol (5 ml) and water (5 ml). The reaction mixture was heated to 80° 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=5. The solid was collected and washed with DMF (5 ml) and acetonitrile (5 ml) to afford the title compound (0.19 g). δH (DMSO-d6, 400 MHz): 1.39 (6H, d), 2.05 (2H, m), 2.40 (2H, m), 3.37 (2H, m), 5.46 (1H, m), 7.88 (1H, dd), 8.57 (5H, m), 8.97 (1H, d), 12.04 (1H, s). MS (ES): C23H21ClN4O4 requires 452. found 453.2 (M+H+).

Workup

  1. temperatureAfter cooling
  2. customisopropanol was evaporated in vacuo
  3. customThe solid was collected
  4. washwashed with DMF (5 ml) and acetonitrile (5 ml)

Sources & evidence

ORD record
ord-8be6992cea19494ba15f30a0c9ec6849
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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