Sodium Hydroxide → HCID 68506057, compound

HRID 1711772Notes

Reaction equation

HRID 1711772 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]4[N:20]([C:22]([C@@H:25]5[CH2:27][C@H:26]5[C:28]([O:30]CC)=[O:29])=[N:23][N:24]=4)[CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]4[N:20]([C:22]([C@@H:25]5[CH2:27][C@H:26]5[C:28]([OH:30])=[O:29])=[N:23][N:24]=4)[CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86621219HCID 86621219, compound

Product 1

HCID 68506057HCID 68506057, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (1R,2R)-ethyl 2-(6-(6-(4-fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)cyclopropanecarboxylate (0.15 g, 0.35 mmol; Example #K.1.1.17) in 1,4-dioxane (10 mL) was treated with 1N NaOH solution (6 mL, 6 mmol). The reaction mixture was stirred at about 60° C. for about 3 h. The organic solvent was removed under reduced pressure. The aqueous layer was acidified to about pH 6 using 1N HCl. The precipitate was filtered, dried in a heated vacuum oven at about 60° C., to give the title compound (0.140 g, 99%) LC/MS (Table 1, Method a) Rt, =1.72 min; MS m/z: 404.1 (M+H)+.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. filtrationThe precipitate was filtered
  3. customdried in a heated vacuum oven at about 60° C.

Sources & evidence

ORD record
ord-cf91fb770c7f44949cc50a2b5b3c0bbd
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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