Hydrochloric Acid → HCID 18975444, compound

HRID 2393360Notes

Reaction equation

HRID 2393360 reaction equation
C(OC([O:6][C:7]1[C:8]2[N:9]([CH:28]=[CH:29][N:30]=2)[C:10]2[C:19](C([O-])=O)([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:11]=2[N:12]=1)=O)C.[ClH:31].C(OCC)(=O)C>O1CCCC1.O>[ClH:31].[CH:28]1[N:9]2[C:10]3[CH:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[C:11]=3[NH:12][C:7](=[O:6])[C:8]2=[N:30][CH:29]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 131720820HCID 131720820, compound

Product 1

HCID 18975444HCID 18975444, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.22 g of ethyl 4-ethoxycarbonyloxy-10H-imidazo[1,2-a]indeno[1,2-e]-pyrazine-10,10-dicarboxylate in 20 ml of tetrahydrofuran are added 5.5 ml of 1N hydrochloric acid at a temperature in the region of 20° C. After reacting overnight at the same temperature, the tetrahydrofuran is evaporated off under reduced pressure (15 mmHg; 2 kPa) and the aqueous solution thus obtained is diluted with 5 ml of distilled water. The addition of 10 ml of ethyl acetate causes formation of a cream-coloured precipitate which is filtered off, washed and dried to give 0.15 g of ethyl 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one-10-carboxylate hydrochloride in the form of a cream-coloured solid (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: 1.23 (t, J=7.5 Hz, 3H: --CH3 ethyl); from 4.00 to 4.40 (mt, 2H: --OCH2 -ethyl); 5.41 (s, 1H: --CH-- 10); 7.43 and 7.51 (2 broad t, J=8 Hz, 1H each: --H 7 and --H 8); 7.75 and 7.97 (2 broad d, J=8 Hz, 1H each: --H 6 and --H 9); 7.82 and 8.14 (2s, 1H each: --H of the imidazole); 12.95 (mult., 1H: --CONH--)).

Workup

  1. customthe tetrahydrofuran is evaporated off under reduced pressure (15 mmHg; 2 kPa)
  2. customthe aqueous solution thus obtained
  3. filtrationis filtered off
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-476f9a87ffcf44cfb1d6a66291f66aef
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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