Tetrahydrofuran → HCID 68777919, compound

HRID 2263010Notes

Reaction equation

HRID 2263010 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[S:23][N:22]=[C:21]([N:24]4[CH2:29][CH2:28][CH:27]([C:30]([O:32]CC)=[O:31])[CH2:26][CH2:25]4)[N:20]=3)[CH2:15][CH2:14]2)=[O:12])=[N:2]1.[OH-].[Na+].O1CCCC1>C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[S:23][N:22]=[C:21]([N:24]4[CH2:25][CH2:26][CH:27]([C:30]([OH:32])=[O:31])[CH2:28][CH2:29]4)[N:20]=3)[CH2:15][CH2:14]2)=[O:12])=[N:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68778050HCID 68778050, compound

Product 1

HCID 68777919HCID 68777919, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixed solution of ethyl 1-(5-{4-[(1,2-benzisoxazol-3-ylamino)carbonyl]piperazin-1-yl}-1,2,4-thiadiazol-3-yl)piperidine-4-carboxylate (60.0 mg, 0.124 mmol), an aqueous 1 N sodium hydroxide solution (0.992 ml, 0.992 mmol), tetrahydrofuran (3 ml) and ethanol (3 ml) was stirred at 80° C. for 5 hours. The solvent was distilled off under reduced pressure. The residue was adjusted to pH 3 by addition of an aqueous 1 N sodium hydroxide solution. A solid was separated by filtration and washed with water to give 17.0 mg (30.0%) of the desired product.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionThe residue was adjusted to pH 3 by addition of an aqueous 1 N sodium hydroxide solution
  3. customA solid was separated by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-06b71acc71604eddad377f9df0f263f9
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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