Sodium Hydroxide → HCID 178448830, compound

HRID 44672Notes

Reaction equation

HRID 44672 reaction equation
[CH3:1][C:2]([C:7]1[N:8]=[C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]3[NH:18][N:19]=[CH:20][C:13]=23)[S:10][CH:11]=1)([CH2:5]C)[C:3]#[N:4].[OH-].[Na+].[Cl:23][O-].[Na+]>O.C([O-])([O-])=O.[Na+].[Na+]>[Cl:23][C:20]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][C:12]=2[C:9]2[S:10][CH:11]=[C:7]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])[N:8]=2)[NH:18][N:19]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 23665760Sodium HypochloriteHCID 68791951HCID 68791951, compound

Product 1

HCID 178448830HCID 178448830, compoundYield 4.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-methyl-2-[2-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiazol-4-yl]butanenitrile (82 mg, 0.2894 mmol) was suspended in a solution of NaOH (46.32 mg, 1.158 mmol) in Water (5.000 mL). The mixture was sonicated to give smaller particle size and cooled in an ice-bath. Sodium hypochlorite (282.8 μL of 8% w/v, 0.3039 mmol) was added slowly dropwise over 2 minutes and the resultant mixture was stirred at ambient temperature for 3 hours. The reaction was diluted with saturated aqueous Na2CO3 and then extracted twice with EtOAc. The combined organics were dried (MgSO4), filtered, concentrated and purified by column chromatography (1:1, Petroleum ether/EtOAc) to give the pure compound as a white solid (3.9 mg, 4% Yield). 1H NMR (DMSO, 400 MHz) δ 0.93 (3H, t), 1.76 (3H, s), 1.99-2.21 (2H, m), 7.54 (1H, s), 8.00 (1H, s), 8.71 (1H, s), 14.29 (1H, br s); MS (ES+) 318.08

Workup

  1. customThe mixture was sonicated
  2. customto give smaller particle size
  3. temperaturecooled in an ice-bath
  4. extractionextracted twice with EtOAc
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography (1:1, Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-c3526245d49e4d7e8234897e99cd7217
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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