Isobutylene oxide → HCID 67009096, compound

HRID 2048427Notes

Reaction equation

HRID 2048427 reaction equation
[O:1]=[C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)=[C:6]([CH2:23][CH2:24][CH3:25])[N:5]2[N:26]=[CH:27][N:28]=[C:4]2[N:3]1[CH:29]1[CH2:37][CH2:36][C:35]2[NH:34][N:33]=[CH:32][C:31]=2[CH2:30]1.[H-].[Na+].CN(C)C(=O)C.[CH3:46][C:47]1([CH3:50])[CH2:49][O:48]1>O.C(OCC)(=O)C>[OH:48][C:47]([CH3:50])([CH3:49])[CH2:46][N:34]1[C:35]2[CH2:36][CH2:37][CH:29]([N:3]3[C:2](=[O:1])[C:7]([CH2:8][C:9]4[CH:10]=[CH:11][C:12]([C:15]5[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=5)=[CH:13][CH:14]=4)=[C:6]([CH2:23][CH2:24][CH3:25])[N:5]4[N:26]=[CH:27][N:28]=[C:4]34)[CH2:30][C:31]=2[CH:32]=[N:33]1

Participants

7

Reactant 4

HCID 11208Isobutylene oxideHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 67009906HCID 67009906, compound

Product 1

HCID 67009096HCID 67009096, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4′-{[5-oxo-7-propyl-4-(4,5,6,7-tetrahydro-1H-indazol-5-yl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.36 g), sodium hydride (0.044 g) and N,N-dimethylacetamide (3 mL) was stirred at 0° C. for 5 min and then at room temperature for 20 min. 2,2-Dimethyloxirane (0.65 mL) was added, and the mixture was stirred at 120° C. for 1.5 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.035 g, 8%).

Workup

  1. waitat room temperature for 20 min
  2. stirringthe mixture was stirred at 120° C. for 1.5 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-57f331257c8c42eaac8d9b5741b504d6
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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