Water → HCID 86647604, compound

HRID 1966845Notes

Reaction equation

HRID 1966845 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[CH2:18][C:17]4([CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]4)[O:16][N:15]=3)=[CH:12][N:11]=[C:10]3[N:25]([CH2:29][CH3:30])[N:26]=[C:27]([CH3:28])[C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1.O>ClCCl>[CH3:48][C:38]1[CH:43]=[CH:42][C:41]([S:44]([O:24][CH:21]2[CH2:22][CH2:23][C:17]3([O:16][N:15]=[C:14]([C:13]4[C:8]([NH:7][CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)=[C:9]5[C:27]([CH3:28])=[N:26][N:25]([CH2:29][CH3:30])[C:10]5=[N:11][CH:12]=4)[CH2:18]3)[CH2:19][CH2:20]2)(=[O:46])=[O:45])=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 66732759HCID 66732759, compound

Product 1

HCID 86647604HCID 86647604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-ol (0.0025 mole) (example 26) is dissolved in dichloromethane. Triethyl amine (0.0050 mol) is added at 0° and p-toluene sulphonyl chloride (0.0050 mole) is added. The reaction mixture is stirred for about 5 hrs. Water is added and extraction is done with dichloromethane. The organic layer is washed with brine, dried and concentrated under reduced pressure to give crude product, 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 product, which
  6. customis purified by column chromatography

Sources & evidence

ORD record
ord-e6446d2d771c43c39bba95c099550fbe
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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