Ammonium Chloride → HCID 178438772, compound

HRID 519653Notes

Reaction equation

HRID 519653 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]([CH2:14][C:15]2[C:16](=[O:40])[N:17]([C@H:27]3[CH2:32][CH2:31][C@H:30]([O:33][CH2:34]C(OCC)=O)[CH2:29][CH2:28]3)[C:18]3[N:19]([N:24]=[CH:25][N:26]=3)[C:20]=2[CH2:21][CH2:22][CH3:23])=[CH:11][CH:10]=1)#[N:2].C[Mg]Br.[Cl-].[NH4+]>O1CCCC1>[OH:33][C:30]([CH3:31])([CH3:29])[CH2:34][O:33][C@H:30]1[CH2:29][CH2:28][C@H:27]([N:17]2[C:16](=[O:40])[C:15]([CH2:14][C:12]3[S:13][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:1]#[N:2])=[CH:10][CH:11]=3)=[C:20]([CH2:21][CH2:22][CH3:23])[N:19]3[N:24]=[CH:25][N:26]=[C:18]23)[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compoundHCID 178438773HCID 178438773, compound

Product 1

HCID 178438772HCID 178438772, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl ({trans-4-[6-{[5-(2-cyanophenyl)thiophen-2-yl]methyl}-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl]cyclohexyl}oxy)acetate (0.25 g) was dissolved in tetrahydrofuran (10 mL), and methylmagnesium bromide (1.0 M tetrahydrofuran solution, 0.44 mL) was added at room temperature. The reaction mixture was stirred at 70° C. for 6 hr, saturated aqueous ammonium chloride solution was added to the reaction mixture, 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 (0.12 g, 49%).

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-34bec9c0e6de4676b6817286f6a0bb07
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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