2,5-Dimethoxytetrahydrofuran → HCID 18975396, compound

HRID 2393380Notes

Reaction equation

HRID 2393380 reaction equation
Cl.[NH2:2][CH:3]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2.C([O-])(=O)C.[Na+].CO[CH:27]1[CH2:31][CH2:30][CH:29](OC)O1>C(O)(=O)C.CO>[N:2]1([CH:3]2[C:15]3[N:14]4[CH:16]=[CH:17][N:18]=[C:13]4[C:12](=[O:19])[NH:11][C:10]=3[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]2=3)[CH:27]=[CH:31][CH:30]=[CH:29]1

Participants

6

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 1897547210-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride

Product 1

HCID 18975396HCID 18975396, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 1.4 g of 10-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride in 25 ml of acetic acid are added 0.41 g of anhydrous sodium acetate and 0.66 g of 2,5-dimethoxytetrahydrofuran. The mixture is stirred at boiling for 1 hour 30 minutes and, after cooling to 20° C., the solid formed is isolated by filtration, washed twice with 30 ml in total of distilled water and air-dried. The product obtained (2.45 g) is chromatographed on 25 g of neutral silica gel (0.06-0.20 mm) contained in a column 2.4 cm in diameter, eluting with a dichloromethane/methanol mixture (90/10 by volume) and collecting an 18 ml fraction and a 540 ml fraction. After addition of decolorizing charcoal, the latter fraction is filtered and the filtrate is concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C. The product obtained is suspended for 10 minutes in 5 ml of methanol and then isolated by filtration, washed with 1 ml of methanol and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.6 g of 10-(1-pyrrolyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is thus obtained, decomposing without melting above 260° C. (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: 6.12 (t, J=2 Hz, 2H: --H 3 and --H 4 of the pyrrole); 6.61 (s, 1H: --CH-- 10); 6.91 (t, J=2 Hz, 2H: --H 2 and --H 5 of the pyrrole); 7.08 and 7.34 (2 broad s, 1H each: --H of the imidazole); from 7.30 to 7.55 and 7.93 [mt and d respectively (J=7.5 Hz), 3H and 1H: --H 6, --H 7, --H 8 and --H 9]; 12.60 (broad s, 1H: --CONH--)).

Workup

  1. customthe solid formed
  2. customis isolated by filtration
  3. washwashed twice with 30 ml in total of distilled water
  4. customair-dried
  5. customThe product obtained (2.45 g)
  6. customis chromatographed on 25 g of neutral silica gel (0.06-0.20 mm)
  7. washeluting with a dichloromethane/methanol mixture (90/10 by volume)
  8. customcollecting an 18 ml fraction
  9. additionAfter addition of decolorizing charcoal
  10. filtrationthe latter fraction is filtered
  11. concentrationthe filtrate is concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C
  12. customThe product obtained
  13. customisolated by filtration
  14. washwashed with 1 ml of methanol
  15. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-20fe9bc55a0943c194cdb2ce8aadee9c
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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