Hydrochloric Acid → HCID 18790693, compound

HRID 1075523Notes

Reaction equation

[CH2:1]([NH:3][C:4]([CH2:6][C:7]1[CH:28]=[CH:27][C:26]2[C:12]3[NH:13][C:14](=[O:25])[C:15]4[N:16]([CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[N:19]=4)[C:11]=3[CH2:10][C:9]=2[CH:8]=1)=[O:5])[CH3:2].O1CCOCC1.[OH-].[Na+].Cl>O>[CH2:1]([NH:3][C:4]([CH2:6][C:7]1[CH:28]=[CH:27][C:26]2[C:12]3[NH:13][C:14](=[O:25])[C:15]4[N:16]([CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=4)[C:11]=3[CH2:10][C:9]=2[CH:8]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 850 mg of ethyl 8-(N-ethylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylate, 10 ml of dioxane, 40 ml of distilled water and 5.8 ml of 1N sodium hydroxide solution is stirred under a stream of argon at a temperature in the region of 20° C. overnight. The reaction mixture is cooled to a temperature in the region of 0° C. and neutralized with 5.8 ml of 1N hydrochloric acid. The precipitate obtained is filtered, washed with distilled water a number of times and dried in an oven. 695 mg of 8-(N-ethylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10-H imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid are obtained in the form of a brown solid melting above 300° C. (1H NMR spectrum in d6-DMSO, T=300K, δ in ppm (300 MHz): 1.05 (3H, t, J=6 Hz, CH3), 3.10 (2H, m, NCH2), 3.47 (2H, s, CH2CO), 4.02 (2H, s, CH2), 7.30 (1H, d, J=8 Hz, arom. CH), 7.48 (1H, s, arom. CH), 7.82 (1H, d, J=8 Hz, arom. CH), 8.08 (1H, t, J=5 Hz, NH), 8.52 (1H, s, imidazole H)).

Workup

customThe precipitate obtained
filtrationis filtered
washwashed with distilled water a number of times
customdried in an oven

Sources & evidence

ORD record: ord-85cea56944ee43949f3111f15de4be2b
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05902803

Reaction notes

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