Hydrochloric Acid → HCID 178438750, compound

HRID 1412448Notes

Reaction equation

HRID 1412448 reaction equation
C(OC(=O)[CH2:5][O:6][C@H:7]1[CH2:10][C@@H:9]([N:11]2[C:16](=[O:17])[C:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]#[N:32])=[CH:21][C:20]=3[F:33])=[C:14]([CH2:34][CH2:35][CH3:36])[N:13]3[N:37]=[CH:38][N:39]=[C:12]23)[CH2:8]1)C.C[Mg]Br.Cl>O1CCCC1>[F:33][C:20]1[CH:21]=[C:22]([C:25]2[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:23]=[CH:24][C:19]=1[CH2:18][C:15]1[C:16](=[O:17])[N:11]([C@H:9]2[CH2:10][C@@H:7]([O:6][CH2:5][C:7]([OH:6])([CH3:10])[CH3:8])[CH2:8]2)[C:12]2[N:13]([N:37]=[CH:38][N:39]=2)[C:14]=1[CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 178418573HCID 178418573, compoundHCID 178438755HCID 178438755, compound

Product 1

HCID 178438750HCID 178438750, compoundYield 120.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl[(cis-3-{6-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclobutyl)oxy]acetate (0.29 g) was dissolved in tetrahydrofuran (3 mL), methylmagnesium bromide (1.6 mL, 1.0 M tetrahydrofuran solution) was added dropwise at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was added to 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer 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 column chromatography to give the title compound as a colorless solid (0.17 g, 60%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer 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 column chromatography

Sources & evidence

ORD record
ord-e61e636d6f9d4c7b8d1c0d525cb86f7f
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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