Sodium Hydroxide → 8-(3-carboxymethylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one dihydrate

HRID 481453Notes

Reaction equation

[OH-:1].[Na+].C([O:5][C:6]([CH2:8][NH:9][C:10](=[O:29])[NH:11][C:12]1[CH:28]=[CH:27][C:26]2[C:17]3[NH:18][C:19](=[O:25])[C:20]4[N:21]([CH:22]=[CH:23][N:24]=4)[C:16]=3[CH2:15][C:14]=2[CH:13]=1)=[O:7])C>C(O)C>[OH2:5].[OH2:1].[C:6]([CH2:8][NH:9][C:10](=[O:29])[NH:11][C:12]1[CH:28]=[CH:27][C:26]2[C:17]3[NH:18][C:19](=[O:25])[C:20]4[N:21]([CH:22]=[CH:23][N:24]=4)[C:16]=3[CH2:15][C:14]=2[CH:13]=1)([OH:7])=[O:5]

Participants

Conditions

Temperature: 20 °C

Procedure

20 ml of 30% sodium hydroxide solution are added, at a temperature in the region of 20° C., to 1 g of 8-(3-ethoxycarbonylmethylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one in suspension in 40 ml of ethanol. The reaction is continued for 18 hours at 50° C. After cooling to a temperature in the region of 20° C., the precipitate formed is filtered, then taken up in 20 ml of distilled water and the mixture is acidified using concentrated hydrochloric acid. The suspension is stirred for 2 hours at a temperature in the region of 20° C. and then filtered, washed with water and dried under partial vacuum (1 mm Hg, 0.13 kPa) at 100° C. After recrystallization from dimethylformamide, there is obtained 0.22 g of 8-(3-carboxymethylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one dihydrate in the form of a beige solid, the melting point of which is greater than 260° C. (Analysis C16H12N5O4 2.0.H2O.0.1DMF, % calculated C: 56.64, H: 3.86, N: 20.64, % found C: 56.7, H: 3.8, N: 21.0).

Workup

customthe precipitate formed
filtrationis filtered
filtrationfiltered
washwashed with water
customdried under partial vacuum (1 mm Hg, 0.13 kPa) at 100° C
customAfter recrystallization from dimethylformamide

Sources & evidence

ORD record: ord-87c0dac94bfe4e5998e96841c3e564a9
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789406

Reaction notes

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