Ammonium formate → FK 1052

HRID 486226Notes

Reaction equation

HRID 486226 reaction equation
C([N:8]1[C:12]([CH3:13])=[C:11]([CH2:14][CH:15]2[C:31](=[O:32])[N:19]3[C:20]4[C:25]([C:26]([CH2:27]N(C)C)=[C:18]3[CH2:17][CH2:16]2)=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:10]=[CH:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C.O.O1CCCC1>[CH3:27][C:26]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]2[C:31](=[O:32])[CH:15]([CH2:14][C:11]3[N:10]=[CH:9][NH:8][C:12]=3[CH3:13])[CH2:16][CH2:17][C:18]=12

Participants

7

Reactant 2

HCID 2723923Ammonium formate2×HCID 190973047-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-10-[(dimethylamino)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 125368FK 1052Yield 73%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-10-[(dimethylamino)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one (215 mg), ammonium formate (318 mg), 10% palladium on carbon (107 mg), water (1 ml), ethanol (2 ml), and tetrahydrofuran (1 ml) was heated at 75° C. for 40 minutes and then cooled. Ammonium formate (300 mg), 10% palladium on carbon (110 mg), water (1 ml), and ethanol (2 ml) were added successively to the reaction mixture. Heating at 75° C. was continued for further 1 hour 20 minutes. After cooling, the reaction mixture was filtered and the residue was washed with 10% methanol-chloroform. The filtrate was evaporated in vacuo. The residue was diluted with water and extracted three times with 10% methanol-chloroform. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfte, and evaporated in vacuo. Silica gel column chromatography of the residue using 5% methanol-chloroform as eluent gave 8,9-dihydro-10-methyl-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (108 mg).

Workup

  1. temperaturecooled
  2. temperatureHeating at 75° C.
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. washthe residue was washed with 10% methanol-chloroform
  6. customThe filtrate was evaporated in vacuo
  7. additionThe residue was diluted with water
  8. extractionextracted three times with 10% methanol-chloroform
  9. washThe organic layer was washed with water and brine
  10. dry with materialdried over anhydrous magnesium sulfte
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-ae22a958029a4ab78f0c9326ebea6468
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

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