Methanol → HCID 66940892, compound

HRID 2192510Notes

Reaction equation

HRID 2192510 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[CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].O1CCCC1.CO.[OH-].[Li+:42]>O>[Li+:42].[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[CH2:27][CH2:28][C:29]([O-:31])=[O:30])[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 58149933HCID 58149933, compound

Product 1

HCID 66940892HCID 66940892, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A round bottom flask was charged with ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate (D8; 80 mg, 0.172 mmol), tetrahydrofuran (THF) (4.00 ml), methanol (4.00 ml), water (2 ml) and lithium hydroxide (4.11 mg, 0.172 mmol). The mixture was warmed to 80° C. for 2 h after which time the solvent was removed in vacuo and the resultant red solid triturated with diethyl ether. The resulting slurry was filtered and the solid dried in vacuo to give the title compound as a brick coloured solid (60 mg).

Workup

  1. customwas removed in vacuo
  2. customthe resultant red solid triturated with diethyl ether
  3. filtrationThe resulting slurry was filtered
  4. customthe solid dried in vacuo

Sources & evidence

ORD record
ord-a71655675d4848f09a38afb959fa0f44
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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