Water → HCID 18975383, compound

HRID 2393367Notes

Reaction equation

C([NH:4][C:5]1[CH:28]=[CH:27][C:8]([CH2:9][CH:10]2[C:22]3[N:21]4[CH:23]=[CH:24][N:25]=[C:20]4[C:19](=[O:26])[NH:18][C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=3)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].O>C(O)(=O)C>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]2[C:22]3[N:21]4[CH:23]=[CH:24][N:25]=[C:20]4[C:19](=[O:26])[NH:18][C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=3)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 98 °C

Procedure

A mixture of 0.1 g of 10-(4-acetylamino-benzyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 5 ml of 1N sodium hydroxide and 5 ml of water is heated at 98° C. for 16 hours. After cooling to a temperature in the region of 20° C., the reaction mixture is acidified with 1 ml of acetic acid, filtered and the precipitate formed is washed with 1 ml of methanol and air-dried. 90 mg of 10-(4-aminobenzyl)-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one are obtained in the form of a yellow solid melting above 260° C. (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: 3.19 and 3.42 (2dd, J=15 and 7 Hz and J=15 and 5 Hz respectively, 1H each: Ar--CH2); 4.41 (dd, J=7 and 5 Hz, 1H: --H10); 4.80 (broad mult., 1H: --NH2); 6.22 and 6.40 (2d, J=7.5 Hz, 2H each: aromatic --H); 7.32 (m, 2H: --H7 and --H8); 7.45 and 7.75 (2 broad d, J=7.5 Hz, 1H each: --H6 and --H9); 7.64 and 8.13 (2 broad s, 1H each: --H of the imidazole); 12.23 (broad s, 1H: --CO--NH--)).

Workup

temperatureAfter cooling to a temperature in the region of 20° C.
filtrationfiltered
customthe precipitate formed
washis washed with 1 ml of methanol
customair-dried

Sources & evidence

ORD record: ord-f0d1ead84b77442497cec36536405af9
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807859

Reaction notes

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