Ethanol → Ethyl 4-amino-5-(3-fluoro-4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

HRID 229627Notes

Reaction equation

CCO.[NH2:4][N:5]1[C:9]([C:10]#[N:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([F:21])[CH:13]=2)[C:7]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:6]1.C(O)(=O)C.[CH:31](N)=[NH:32].O>CCOCC>[NH2:11][C:10]1[C:9]2=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([F:21])[CH:13]=3)[C:7]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:6][N:5]2[N:4]=[CH:31][N:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of EtOH (75 mL) was added ethyl 1-amino-5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate (1.68 g, 5.28 mmol) and formamidine acetate (5.49 g, 52.8 mmol). The solution was heated to 80° C. for 17 h. Upon cooling to rt the solution was treated with water and a precipitate formed which was filtered and washed with additional water. The solid was then suspended in DCM and Et2O. The solid was collected and washed with Et2O yielding 1.22 g of an orange-yellow solid (3.52 mmol, yield 67%). 1H-NMR (DMSO-d6) δ 8.20 (s, 1H), 8.18 to 8.14 (t, J=8.2 Hz, 1H), 7.97 (s, 1H), 7.66 to 7.63 (d, J=12.4 Hz, 1H), 7.41 to 7.39 (d, J=8.4 Hz, 1H), 4.12 to 4.07 (q, J=7.0 Hz, 2H), 1.13 to 1.10 (t, J=7.0 Hz, 3H); MS [M+H]+=346.2; LCMS RT=2.77 min.

Workup

temperatureUpon cooling to rt the solution
customa precipitate formed which
filtrationwas filtered
washwashed with additional water
customThe solid was collected

Sources & evidence

ORD record: ord-a7a4ca2e9110417c9f5509aa3a407caa
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563791B2

Reaction notes

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