Water → HCID 86647606, compound

HRID 1966850Notes

Reaction equation

HRID 1966850 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](C)=[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.[N-:41]=[N+:42]=[N-:43].[Na+].O>CN(C)C=O>[N:41]([CH:12]1[CH2:40][CH2:39][C:15]2([O:19][N:18]=[C:17]([C:20]3[CH:25]=[N:24][C:23]4[N:26]([CH2:30][CH3:31])[N:27]=[CH:28][C:22]=4[C:21]=3[NH:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:16]2)[CH2:14][CH2:13]1)=[N+:42]=[N-:43]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86647604HCID 86647604, compound

Product 1

HCID 86647606HCID 86647606, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

3-[4-(Cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-yl 4-methylbenzenesulfonate (0.00090 mole) (example 39) is taken in dimethylformamide. Sodium azide (0.0027 mole) is added. The reaction mixture is stirred at 60-70° C. overnight. It is cooled and 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. temperatureIt is cooled
  2. extractionextraction
  3. washThe organic layer is washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto give crude compound, which
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-200a446f100c47339217f82056d70804
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

Loading…