Hydrochloric Acid → HCID 131721164, compound

HRID 1418299Notes

Reaction equation

HRID 1418299 reaction equation
[O:1]1CC[CH2:3][CH2:2]1.[NH2:6][C:7]1[C:8]([Cl:25])=[CH:9][C:10]([F:24])=[C:11]([N:13]2[C:21](=[O:22])[C:16]3=[CH:17][CH2:18][CH2:19][CH2:20][N:15]3[C:14]2=[O:23])[CH:12]=1.C(OC(=O)C)(=O)C.Cl>N1C=CC=CC=1.C(OCC)(=O)C>[C:2]([NH:6][C:7]1[C:8]([Cl:25])=[CH:9][C:10]([F:24])=[C:11]([N:13]2[C:21](=[O:22])[C:16]3=[CH:17][CH2:18][CH2:19][CH2:20][N:15]3[C:14]2=[O:23])[CH:12]=1)(=[O:1])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 131721162HCID 131721162, compound

Product 1

HCID 131721164HCID 131721164, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an tetrahydrofuran (5 mL) solution of 2-(5-amino-4-chloro-2-fluorophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.50 g, 1.69 mmol) were dropwise added acetic anhydride (0.18 mL, 1.86 mmol) and pyridine (8 drops) with stirring at room temperature. The reaction mixture was stirred for 8 hours at room temperature and further stirred for 13 hours at 80° C. 1N Hydrochloric acid (20 mL) and ethyl acetate (20 mL) were added to the resulting mixture, and the organic layer was separated and the aqueous layer was extracted with ethyl acetate (20 mL×2 times). The organic layer combined was washed with saturated sodium chloride solution (30 mL) and dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was evaporated to give crude product, which was purified by silica gel column (Wakogel C-200, ethyl acetate/hexane =1/1) to obtain a white solid of 2-(5-acetylamino-4-chloro-2-fluorophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.34 g, yield:59.6%).

Workup

  1. stirringThe reaction mixture was stirred for 8 hours at room temperature
  2. stirringfurther stirred for 13 hours at 80° C
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (20 mL×2 times)
  5. washThe organic layer combined was washed with saturated sodium chloride solution (30 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removal of magnesium sulfate
  8. filtrationby filtration
  9. customthe filtrate was evaporated
  10. customto give crude product, which
  11. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane =1/1)

Sources & evidence

ORD record
ord-10a04c23dc2d43558a1dc17d28f1281d
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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