tert-Butanol → HCID 58547265, compound

HRID 1850355Notes

Reaction equation

HRID 1850355 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([C:15]2[C:16]([C:21]3[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=3)[C:24]#[N:25])=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:12]1.[OH-].[K+].CC([OH:35])(C)C>O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([C:15]2[C:16]([C:21]3[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=3)[C:24]([NH2:25])=[O:35])=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 54675454HCID 54675454, compound

Product 1

HCID 58547265HCID 58547265, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)benzonitrile (0.072 g, 0.198 mmol), potassium hydroxide (0.111 g, 1.981 mmol, v/w) and t-BuOH (2 mL, Acros) was heated at 80° C. overnight. LCMS showed the product. The mixture was diluted with water and extracted with a mixture of CHCl3:i-PrOH (3:1) three times. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The product was obtained as a white solid (75 mg, 99%).

Workup

  1. extractionextracted with a mixture of CHCl3:i-PrOH (3:1) three times
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f75b988325364454b3cbf2b521995138
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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