Hydrochloric Acid → HCID 178438632, compound

HRID 1412313Notes

Reaction equation

HRID 1412313 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:43])[N:18]([C@H:29]3[CH2:34][CH2:33][C@H:32]([O:35][CH2:36][C:37](N(OC)C)=[O:38])[CH2:31][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])=[CH:11][CH:10]=1)#[N:2].[CH3:44][Mg]Br.Cl>O1CCCC1>[CH3:28][C:26]1[N:27]=[C:19]2[N:18]([C@H:29]3[CH2:30][CH2:31][C@H:32]([O:35][CH2:36][C:37](=[O:38])[CH3:44])[CH2:33][CH2:34]3)[C:17](=[O:43])[C:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:4]4[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=4)=[CH:10][CH:11]=3)=[C:21]([CH2:22][CH2:23][CH3:24])[N:20]2[N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 178418573HCID 178418573, compoundHCID 178438671HCID 178438671, compound

Product 1

HCID 178438632HCID 178438632, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[(trans-4-{6-[(2′-Cyanobiphenyl-4-yl)methyl]-2-methyl-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexyl)oxy]-N-methoxy-N-methylacetamide (1 g) was dissolved in tetrahydrofuran (15 mL), and methylmagnesium bromide (1.0 M tetrahydrofuran solution, 1.7 mL) was added at room temperature. The reaction mixture was stirred for 1 hr, 1 N hydrochloric acid was added, and the mixture was extracted with 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 (0.56 g, 60%).

Workup

  1. extractionthe mixture was extracted with 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-89af79d939194ccd86ab176d3986e5d2
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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