Benzoylhydrazine → 3-phenyl-9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepine

HRID 44219

Reaction equation

[C:1]([NH:9][NH2:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CS[C:25]1[C:26]2[CH:39]=[CH:38][CH:37]=[CH:36][C:27]=2[NH:28][C:29]2[N:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1>CO.ClCCl>[C:2]1([C:1]2[N:31]3[C:30]4[CH:32]=[CH:33][CH:34]=[N:35][C:29]=4[NH:28][C:27]4[CH:36]=[CH:37][CH:38]=[CH:39][C:26]=4[C:25]3=[N:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution benzoic hydrazide (0.98 g, 7.2 mmol) and p-toluenesulfonic acid monohydrate (0.68 g, 3.6 mmol) in methanol (50 ml) was added a solution of 6-(methylthio)-11H-benzo[e]pyrido[3,2-b][1,4]diazepine (0.87 g, 3.6 mmol) in dichloromethane (25 ml). The reaction mixture was heated at 90° C. for 3 hours. The solvent was removed under reduced pressure and the crude product purified using flash chromatography (SiO2, 2% MeOH in DCM). The desired product, 3-phenyl-9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepine, was obtained as a tan solid (0.352 mg, 31%). M.p.=273-275° C.; 400 MHz 1H NMR (CDCl3) δ: 8.20 (d, J=7.8 Hz, 1H), 8.17 (d, J=3.9 Hz, 1H), 7.5-7.3 (m, 6H), 7.18 (t, J=7.6 Hz, 1H), 7.04 (d, J=7.8 Hz, 1H), 7.00 (d, J=8.2 Hz, 1H), 6.79 (dd, J=7.8, 4.7 Hz, 1H), 6.49 (s, 1H); LCMS [M+H]: 312; Calculated for C19H13N5. 0.44 water, C, 71.48; H 4.38; N 21.94, found, C 71.48, H 4.43, N 21.67.

Workup

customThe solvent was removed under reduced pressure
customthe crude product purified

Sources & evidence

ORD record: ord-c451f4739c614faa8f7ea4660f33ccae
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541407B2

Linked notes

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