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Dimethyl Sulfoxide → HCID 178454109, compound

HRID 707330
Notes
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Reaction equation

HRID 707330 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][NH2:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[C:21]([C:22]#[N:23])=[CH:20][CH:19]=[CH:18][N:17]=1.C([O-])(=O)C.[Cs+].CS(C)=O>C(OCC)(=O)C.[Cu]>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:9][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:21]3[C:22]([NH2:23])=[N:13]2)[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 810792-ChloronicotinonitrileHCID 5152919Cesium acetateHCID 178454123HCID 178454123, compound

Product 1

HCID 178454109HCID 178454109, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 23978
Copper
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butyl(trans-3-hydrazinylcyclobutyl)carbamate (4 g, 19.87 mmol), 2-chloro-3-cyanopyridine (3 g, 21.65 mmol), cesium acetate (14 g, 72.9 mmol), and copper powder (0.126 g, 1.987 mmol) were placed under nitrogen. Dry dimethylsulfoxide (20 mL) was added and the mixture stirred at 100° C. After 1 hour the mixture was cooled and diluted with ethyl acetate (300 mL). The mixture was filtered through a pad of celite and the filtrate washed with 10% saturated sodium bicarbonate (500 mL) before drying with magnesium sulfate and evaporating to dryness under reduced pressure. Purification using silica chromatography (10% (2 N ammonia in methanol) in dichloromethane) gave the desired tert-butyl(trans-3-(3-amino-1H-pyrazolo[3,4-b]pyridin-1-yl)cyclobutyl)carbamate (2.72 g, 8.97 mmol, 45.1% yield).

Workup

  1. temperatureAfter 1 hour the mixture was cooled
  2. filtrationThe mixture was filtered through a pad of celite
  3. washthe filtrate washed with 10% saturated sodium bicarbonate (500 mL)
  4. dry with materialbefore drying with magnesium sulfate
  5. customevaporating to dryness under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-f4e1ef529cb04012ac66626148105e9e
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174992B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes