Hydrochloric Acid → HCID 18918170, compound

HRID 1290770Notes

Reaction equation

HRID 1290770 reaction equation
C([O-])(=O)C.[NH4+].[F:6][C:7]1[CH:23]=[CH:22][C:21]2[C:12]3[NH:13][C:14](=[O:20])[C:15]4[N:16]([CH:17]=[CH:18][N:19]=4)[C:11]=3[C:10](=[N:24]O)[C:9]=2[CH:8]=1.C(O)C.[ClH:29]>N.O.CO.[Zn]>[ClH:29].[NH2:24][CH:10]1[C:11]2[N:16]3[CH:17]=[CH:18][N:19]=[C:15]3[C:14](=[O:20])[NH:13][C:12]=2[C:21]2[CH:22]=[CH:23][C:7]([F:6])=[CH:8][C:9]1=2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 517165Ammonium AcetateHCID 178518653HCID 178518653, compound

Product 1

HCID 18918170HCID 18918170, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 222AmmoniaSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.48 g of ammonium acetate in 120 ml of 28% aqueous ammonia solution are successively added 3.25 g of 8-fluoro-10-hydroxyimino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 120 ml of ethanol and 3.55 g of zinc powder. The mixture is stirred for 2 hours at boiling and for 16 hours at a temperature in the region of 20° C., followed by dropwise addition of 60 ml of aqueous 5N hydrochloric acid solution and the mixture is stirred for 16 hours at the same temperature. The insoluble material formed is removed by filtration and the filtrate is concentrated to dryness under reduced pressure (10 mmHg; 1.3 kPa) at 50° C. The product obtained (13.4 g) is stirred in suspension in 30 ml of distilled water and the insoluble material is separated out by filtration, washed twice with 4 ml in total of distilled water and dried under reduced pressure (10 mmHg; 1.3 kPa) at 50° C. The product obtained (1.35 g) is suspended for 10 minutes in 10 ml of boiling methanol. After cooling and storing for 16 hours at 5° C., the insoluble material is separated out by filtration, washed with 1 ml of methanol and resuspended for 10 minutes in 5 ml of boiling methanol. After cooling and storing for 6 hours at 5° C., the insoluble material is separated out by filtration, washed with 1 ml of methanol and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.48 g of 10-amino-8-fluoro-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one hydrochloride is thus obtained, decomposing without melting above 260° C. [N.M.R. spectrum: [200 MHz; (CD3)2SO d6 ; δ in ppm]: 5.69 (broad s, 1H: --CH-- 10); 7.44 (dt, J=8.5 and 2 Hz, 1H: --H7); 7.68 and 8.54 (2s, 1H each: --H of the imidazole); 7.93 (dd, J=8.5 and 2 Hz, 1H: --H9); 7.94 (dd, J=8.5 and 6 Hz, 1H: --H6); 9.30 (cplx, 3H: --NH3+Cl- ; 12.72 (wide cplx, 1H: --CONH--)].

Workup

  1. waitat boiling and for 16 hours at a temperature in the region of 20° C.
  2. stirringthe mixture is stirred for 16 hours at the same temperature
  3. customThe insoluble material formed
  4. customis removed by filtration
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (10 mmHg; 1.3 kPa) at 50° C
  6. customThe product obtained (13.4 g)
  7. customthe insoluble material is separated out by filtration
  8. washwashed twice with 4 ml in total of distilled water
  9. customdried under reduced pressure (10 mmHg; 1.3 kPa) at 50° C
  10. customThe product obtained (1.35 g)
  11. temperatureAfter cooling
  12. waitstoring for 16 hours at 5° C.
  13. customthe insoluble material is separated out by filtration
  14. washwashed with 1 ml of methanol
  15. waitresuspended for 10 minutes in 5 ml of boiling methanol
  16. temperatureAfter cooling
  17. waitstoring for 6 hours at 5° C.
  18. customthe insoluble material is separated out by filtration
  19. washwashed with 1 ml of methanol
  20. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-9a0c4eaf96644792a7379d1fa010a8a8
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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