Hydrochloric Acid → [4-[5-[3-Amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl acetate

HRID 78641Notes

Reaction equation

HRID 78641 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH:31]=[CH:30][C:24]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])=[CH:23][CH:22]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=2)=[N:11][N:12]=1.[C:32]([O-:35])(=[O:34])[CH3:33].[K+].Cl>CN(C=O)C>[C:32]([O:35][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[O:9][C:8]([C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:21]4[CH:22]=[CH:23][C:24]([C:25](=[O:26])[N:27]([CH3:29])[CH3:28])=[CH:30][CH:31]=4)[N:6]=3)=[N:12][N:11]=2)=[CH:14][CH:15]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 59471628HCID 59471628, compound

Product 1

HCID 59471775[4-[5-[3-Amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl acetateYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-[5-amino-6-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide (200 mg, 0.4172 mmol) and potassium acetate (102.4 mg, 1.043 mmol) in DMF (5.714 mL) was heated at 100° C. for 4 h in a sealed microwave tube. The reaction mixture was cooled to room temperature and poured onto ice/water and acidified by HCl (1.043 mL of 1 M, 1.043 mmol). The mixture was extracted with ethyl acetate (3×10 mL) and the combined organic extracts washed with brine (3×10 mL). The extracts were dried over MgSO4 and concentrated under reduced pressure to give a yellow solid (150 mg, 74% yield); 1H NMR (400 MHz, DMSO) d 2.13 (s, 3H), 2.98-3.02 (m, 6H), 5.22 (s, 2H), 7.55 (d, 2H), 7.66 (d, 2H), 7.78 (br s, 2H), 8.16-8.19 (m, 4H) and 8.99 (s, 1H) ppm; MS (ES+) 459.18

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured onto ice/water
  3. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  4. washthe combined organic extracts washed with brine (3×10 mL)
  5. dry with materialThe extracts were dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfd38fdf965a42aa960ebefdddcd4e30
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

Loading…