HCID 178420675, compound → HCID 178438748, compound

HRID 1688757Notes

Reaction equation

HRID 1688757 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[C:17](=[O:40])[N:18]([C@@H:29]3[CH2:32][C@H:31]([O:33][CH2:34]C(OCC)=O)[CH2:30]3)[C:19]3[N:20]([N:25]=[C:26]([CH3:28])[N:27]=3)[C:21]=2[CH2:22][CH2:23][CH3:24])=[C:11]([F:41])[CH:10]=1)#[N:2].[CH3:42][Mg]Br.[O:45]1[CH2:49][CH2:48]CC1>O1CCCC1.[Cl-].[NH4+]>[F:41][C:11]1[CH:10]=[C:9]([C:4]2[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:14]=[CH:13][C:12]=1[CH2:15][C:16]1[C:17](=[O:40])[N:18]([C@H:29]2[CH2:30][C@@H:31]([O:33][CH2:34][C:49]([OH:45])([CH3:48])[CH3:42])[CH2:32]2)[C:19]2[N:20]([N:25]=[C:26]([CH3:28])[N:27]=2)[C:21]=1[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 178420675HCID 178420675, compoundHCID 178438753HCID 178438753, compound

Product 1

HCID 178438748HCID 178438748, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of ethyl [(cis-3-{6-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-2-methyl-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclobutyl)oxy]acetate (895 mg) in tetrahydrofuran (8 mL) was added 1 M methylmagnesium bromide-tetrahydrofuran solution (8 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=65/35→40/60 (volume ratio)] to give the title compound as a colorless amorphous compound (606 mg, 70%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=65/35→40/60 (volume ratio)]

Sources & evidence

ORD record
ord-e6f497c944f949db988ce427df1bfc76
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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