Potassium Hydroxide → HCID 178434399, compound

HRID 1526113Notes

Reaction equation

HRID 1526113 reaction equation
CN(C)CCC[OH:6].[OH-].[K+].Cl/[C:11](/[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[CH:12]\[C:13]1[C:18]([C:19]#[N:20])=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=2)[N:16]=[C:15]2[NH:29][N:30]=[C:31]([CH3:32])[C:14]=12.B(Br)(Br)Br>CS(C)=O.O>[OH:27][C:24]1[CH:23]=[CH:22][C:21]([C:17]2[N:16]=[C:15]3[NH:29][N:30]=[C:31]([CH3:32])[C:14]3=[C:13]([CH2:12][C:11](=[O:6])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:18]=2[C:19]#[N:20])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 25134Boron tribromideHCID 766463-(Dimethylamino)-1-propanolHCID 178488914HCID 178488914, compound

Product 1

HCID 178434399HCID 178434399, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

36 g (350 mmol) of 3-(dimethylamino)propan-1-ol and 12 g (21.4 mmol) of potassium hydroxide are added to 12 g (30 mmol) of Z-4-(2-chloro-2-phenylvinyl)-6-(4-methoxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile dissolved in 100 ml of dimethylsulfoxide and 36 ml of water. The reaction mixture is carried at 120° C. for 3 hours. The reaction medium is cooled to room temperature and then poured over crushed ice. The product is extracted with ethyl acetate. The organic phases are dried on sodium sulfate, filtered and then concentrated. The residue is purified immediately by silica gel chromatography (eluent: 95:5 dichloromethane/methanol). The product is then dissolved in 100 ml of dichloromethane. The reaction medium is cooled in an ice bath before 36 ml (376.5 mmol) of boron tribromide is added slowly. The reaction medium is stirred at room temperature for 3 hours and then added slowly to crushed ice. The solid is filtered, rinsed with water, dried and then purified by silica gel chromatography (eluent: 5:5 cyclohexane/ethyl acetate) to yield 6 g (54%) of 6-(4-hydroxyphenyl)-3-methyl-4-(2-oxo-2-phenylethyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a yellow solid.

Workup

  1. additionpoured
  2. customover crushed ice
  3. extractionThe product is extracted with ethyl acetate
  4. customThe organic phases are dried on sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified immediately by silica gel chromatography (eluent: 95:5 dichloromethane/methanol)
  8. dissolutionThe product is then dissolved in 100 ml of dichloromethane
  9. additionis added slowly
  10. additionadded slowly
  11. customto crushed ice
  12. filtrationThe solid is filtered
  13. washrinsed with water
  14. customdried
  15. custompurified by silica gel chromatography (eluent: 5:5 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-c07ab336297f4aa99c0d99391244bb1f
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

Loading…