Ethyl trifluoroacetate → HCID 140392638, compound

HRID 2393361Notes

Reaction equation

[NH2:1][CH:2]1[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.FC(F)(F)C(OCC)=O>CN(C)C=O>[NH:1]=[C:2]1[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 0.5 g of 10-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 15 ml of dimethylformamide is added 0.6 ml of ethyl trifluoroacetate at a temperature in the region of 20° C. The reaction medium is heated at 60° C. for 5 hours and is then cooled and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa). The residue is taken up in dichloromethane and the insoluble product is filtered off, washed and dried. After purification by flash chromatography using a mixture of ethyl acetate and methanol (90/10 by volume) as eluent, 0.06 g of 10-imino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained in the form of a reddish powder, the melting point of which is greater than 260° C. (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: from 7.20 to 7.50 (mt, 2H: --H 7 and --H 8); 7.57 and 8.33 (2s, 1H each: --H of the imidazole); 7.65 and 7.86 (2 broad d, J=8 Hz, 1H each: --H 6 and --H 9); from 11.10 to 12.10 (broad mult., 1H: --CONH--)).

Workup

temperatureis then cooled
concentrationconcentrated to dryness under reduced pressure (15 mmHg; 2 kPa)
filtrationthe insoluble product is filtered off
washwashed
customdried
customAfter purification by flash chromatography
additiona mixture of ethyl acetate and methanol (90/10 by volume) as eluent

Sources & evidence

ORD record: ord-4d41168c18c44548b773598e64a27dd2
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807859

Reaction notes

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