Water → HCID 86647602, compound

HRID 1966831Notes

Reaction equation

[OH-].[K+].Cl[CH2:4][C:5]#[N:6].[CH:7]1([NH:13][C:14]2[C:19]([C:20]3[CH2:24][C:23]4([CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]4)[O:22][N:21]=3)=[CH:18][N:17]=[C:16]3[N:31]([CH2:34][CH3:35])[N:32]=[CH:33][C:15]=23)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCCC1>[CH:7]1([NH:13][C:14]2[C:19]([C:20]3[CH2:24][C:23]4([CH2:29][CH2:28][C:27]5([O:30][CH:4]5[C:5]#[N:6])[CH2:26][CH2:25]4)[O:22][N:21]=3)=[CH:18][N:17]=[C:16]3[N:31]([CH2:34][CH3:35])[N:32]=[CH:33][C:15]=23)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

Benzyltriethyl ammonium chloride (23 mg, 0.00001 mole) was added to a mixture of 50% potassium hydroxide solution and tetrahydrofuran (10 ml) and the mixture was cooled to 0° C. Chloroacetonitrile (0.020 ml, 0.00026 mole) and 3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-one (100 mg, 0.00025 mole) (example 25) in tetrahydrofuran were added to the reaction mixture. It was stirred for about 4 hours at room temperature and water was added. The reaction mixture was extracted with ethyl acetate, organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by preparative thin layer chromatography.

Workup

extractionThe reaction mixture was extracted with ethyl acetate, organic layer
washwas washed with brine
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure
customThe crude product was purified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-38b676421dc343a7b9019d07c0418bf5
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420666B2

Reaction notes

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