Hydrazinecarboxaldehyde → N-[2-methyl-5-(1H-1,2,4-triazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide

HRID 406836Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:11])OC)=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)=[CH:17][CH:16]=1)=[O:14].[CH:38]([NH:40][NH2:41])=O.CCN(C(C)C)C(C)C>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:41][N:40]=[CH:38][N:11]=2)=[CH:4][C:3]=1[NH:12][C:13](=[O:14])[C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]2[N:31]=[C:30]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of methyl 4-methyl-3-[({4-[(4-phenylquinazolin-2-yl)amino]phenyl}carbonyl)amino]benzenecarboximidoate (50 mg, 0.10 mmol), formylhydrazine (30 mg, 0.5 mmol) and Hunig's base (17 μL, 0.20 mmol) in ethanol (2 mL) was heated to 150° C. in a sealed tube overnight. The reaction was cooled to rt and concentrated on a rotary evaporator. The residue was purified by preparative reverse phase HPLC to give N-[2-methyl-5-(1H-1,2,4-triazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide (10.9 mg, 22%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.34 (s, 1H), 9.84-9.82 (m, 2H), 8.62 (s, 1H), 8.19 (d, 2H), 8.06-7.99 (m, 3H), 7.90-7.78 (m, 5H), 7.66-7.63 (m, 3H), 7.42 (ddd, 1H), 7.36 (d, 1H), 2.36 (s, 3H). MS (EI) for C30H23N7O: 498.2 (MH+).

Workup

temperatureThe reaction was cooled to rt
concentrationconcentrated on a rotary evaporator
customThe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-78e227c0c53b4a1caee30a16d28edc39
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754092B2

Reaction notes

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