Hydrochloric Acid → HCID 66749802, compound

HRID 537052Notes

Reaction equation

HRID 537052 reaction equation
C[Mg]Br.[C:4]([NH:7][C:8]1[CH:13]=[C:12]([C:14]2[O:15][C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[C:17]([C:19](N(OC)C)=[O:20])[N:18]=2)[C:11]([CH3:32])=[CH:10][N:9]=1)(=[O:6])[CH3:5].Cl.[C:34]([O-])(O)=O.[Na+]>>[C:19]([C:17]1[N:18]=[C:14]([C:12]2[C:11]([CH3:32])=[CH:10][N:9]=[C:8]([NH:7][C:4](=[O:6])[CH3:5])[CH:13]=2)[O:15][C:16]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])(=[O:20])[CH3:34]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86666248HCID 86666248, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 66749802HCID 66749802, compoundYield 54%

Procedure

Methylmagnesium bromide (3.0 M in diethyl ether, 0.18 mL, 0.53 mmol) was added to 2-(2-acetamido-5-methylpyridin-4-yl)-5-(2-chlorophenyl)-N-methoxy-N-methyl-1,3-oxazole-4-carboxamide (0.19 g. 0.45 mmol) in THY (1 mL) under an atmosphere of argon at 0° C. The reaction mixture was allowed to warm to rt and stir overnight and then additional methylmagnesium bromide (3.0 M in diethyl ether, 0.30 mL, 0.90 mmol) was added. The reaction mixture was then allowed to stir for 24 hr. Aqueous HCl was added and then the mixture was basified with NaHCO3 and washed with EtOAc. The organic solutions were combined, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-{4-[4-acetyl-5-(2-chlorophenyl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (0.12 g, 54%). LCMS (FA): m/z=370.0 (M+H).

Workup

  1. stirringto stir for 24 hr
  2. washwashed with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-102fd6e57d334141b2c96af7ae5551b4
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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