HCID 178420675, compound → HCID 178438749, compound

HRID 519786Notes

Reaction equation

HRID 519786 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 178438754HCID 178438754, compound

Product 1

HCID 178438749HCID 178438749, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of ethyl [(trans-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 (557 mg) in tetrahydrofuran (5 mL) was added 1 M methylmagnesium bromide-tetrahydrofuran solution (5 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 (437 mg, 80%).

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-1c18e1f49cd24779a4c1a1be533a42e4
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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