Methanol → HCID 66877619, compound

HRID 2192512Notes

Reaction equation

HRID 2192512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N:21]=[C:22]4[N:27]3[CH2:32][CH2:31][CH:30]([C:33]([O:35]CC)=[O:34])[CH2:29][CH2:28]3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].O1CCCC1.CO.[OH-].[Li+:46]>O>[Li+:46].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N:21]=[C:22]4[N:27]3[CH2:32][CH2:31][CH:30]([C:33]([O-:35])=[O:34])[CH2:29][CH2:28]3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58149897HCID 58149897, compound

Product 1

HCID 66877619HCID 66877619, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 1-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]-4-piperidinecarboxylate (D14; 35 mg, 0.067 mmol), tetrahydrofuran (THF) (2.0 ml), methanol (2.0 ml), water (1 ml) and lithium hydroxide (1.61 mg, 0.067 mmol) was left to stir at 80° C. for 3 h. The solvent was removed in vacuo and the residue was triturated with diethyl ether. The mixture was filtered to give the title compound as a pale peach coloured solid (20 mg).

Workup

  1. waitwas left
  2. customThe solvent was removed in vacuo
  3. customthe residue was triturated with diethyl ether
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-4d884fc310b94e0ca257da9371075de8
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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