2-Methyl-2-butene → HCID 178438601, compound

HRID 519606Notes

Reaction equation

HRID 519606 reaction equation
[CH:1]([C:3]1([CH2:7][O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([N:15]3[C:20](=[O:21])[C:19]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]5[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=5)=[CH:25][CH:24]=4)=[C:18]([CH2:37][CH2:38][CH3:39])[N:17]4[N:40]=[CH:41][N:42]=[C:16]34)[CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4]1)=[O:2].Cl([O-])=[O:44].[Na+].P([O-])(O)(O)=O.[Na+].CC(=CC)C>O.O1CCCC1.C(O)CCC>[C:35]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C:19]2[C:20](=[O:21])[N:15]([C@H:12]3[CH2:13][CH2:14][C@H:9]([O:8][CH2:7][C:3]4([C:1]([OH:44])=[O:2])[CH2:6][CH2:5][CH2:4]4)[CH2:10][CH2:11]3)[C:16]3[N:17]([N:40]=[CH:41][N:42]=3)[C:18]=2[CH2:37][CH2:38][CH3:39])=[CH:28][CH:27]=1)#[N:36]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 178438599HCID 178438599, compound

Product 1

HCID 178438601HCID 178438601, compoundYield 65.3%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4′-[(4-{trans-4-[(1-formylcyclobutyl)methoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (0.7 g), sodium chlorite (0.21 g), sodium dihydrogen phosphate (0.15 g), 2-methyl-2-butene (0.53 mL), n-butanol (10 mL), tetrahydrofuran (5 mL) and water (5 mL) was stirred at room temperature for 16 hr. The reaction mixture was extracted with 1 N hydrochloric acid and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.47 g, 65%).

Workup

  1. extractionThe reaction mixture was extracted with 1 N hydrochloric acid and ethyl acetate
  2. washThe obtained ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4f8eb656eecf462483252dacbd665e41
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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