Tetrahydrofuran → HCID 11993185, compound

HRID 421842Notes

Reaction equation

[NH2:1][C:2](=[N:23][OH:24])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:22])[CH2:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[N:4]=1.[OH-].[Na+].O1CC[CH2:29][CH2:28]1>C(OCC)(=O)C>[CH3:19][C:18]([CH3:20])([CH3:21])[CH2:17][CH2:16][C:15]([N:12]1[CH2:13][CH2:14][N:9]([C:5]2[N:4]=[C:3]([C:2]3[N:1]=[C:28]([CH3:29])[O:24][N:23]=3)[CH:8]=[CH:7][N:6]=2)[CH2:10][CH2:11]1)=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

1-{4-[Amino(hydroxyimino)methyl]pyrimidin-2-yl}-4-(4,4-dimethylpentanoyl)piperazine (186 mg) obtained in Example 64-1) was dissolved in tetrahydrofuran (3 mL), and oily sodium hydroxide (25 mg) was added thereto and stirred at 60° C. for 20 minutes. Then, ethyl acetate (0.082 ml) was added to it and heated under reflux for 1 hour. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (chloroform/methanol=19/1) to obtain 53.4 mg of the entitled compound as a colorless solid.

Workup

temperatureheated
temperatureunder reflux for 1 hour
customThe reaction liquid
washwashed with water and saturated saline water
dry with materialdried with anhydrous sodium sulfate
customThe solvent was evaporated away
customthe resulting residue was isolated
custompurified through thin-layer silica gel chromatography (chloroform/methanol=19/1)

Sources & evidence

ORD record: ord-314ddf6d0bf14b779fbecb6db79c4809
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101618B2

Reaction notes

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