Water → HCID 66732700, compound

HRID 1966846Notes

Reaction equation

HRID 1966846 reaction equation
CC1C=CC(S(O[CH:12]2[CH2:40][CH2:39][C:15]3([O:19][N:18]=[C:17]([C:20]4[C:21]([NH:32][CH:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[C:22]5[C:28]([CH3:29])=[N:27][N:26]([CH2:30][CH3:31])[C:23]5=[N:24][CH:25]=4)[CH2:16]3)[CH2:14][CH2:13]2)(=O)=O)=CC=1.[C-:41]#[N:42].[Na+].O>CN(C)C=O>[CH:33]1([NH:32][C:21]2[C:20]([C:17]3[CH2:16][C:15]4([CH2:14][CH2:13][CH:12]([C:41]#[N:42])[CH2:40][CH2:39]4)[O:19][N:18]=3)=[CH:25][N:24]=[C:23]3[N:26]([CH2:30][CH3:31])[N:27]=[C:28]([CH3:29])[C:22]=23)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 86647604HCID 86647604, compound

Product 1

HCID 66732700HCID 66732700, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
62.5 °C

Procedure

3-[4-(Cyclohexylamino)-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-yl 4-methylbenzenesulfonate (0.0018 mole) (example 39) is taken in dimethylformamide. Sodium cyanide (0.0036 mole) is added and the reaction mixture is stirred at 60-65° C. overnight. Water is added and extraction is done with ethyl acetate. The organic layer is washed with brine, dried and concentrated under reduced pressure to give crude compound, which is purified by column chromatography.

Workup

  1. extractionextraction
  2. washThe organic layer is washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto give crude compound, which
  6. customis purified by column chromatography

Sources & evidence

ORD record
ord-fecd4f0cbf8747f5a6ee63dcabaf61a9
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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