Methanol → HCID 59242068, compound

HRID 1876154Notes

Reaction equation

[CH3:1][N:2]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[C:20]([CH3:28])[N:19]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][NH:13][C:14](OC)=[O:15])=[O:11])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].CO>C1COCC1>[CH3:1][N:2]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[C:20]([CH3:28])[N:19]=1)[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:10](=[O:11])[NH:12][NH:13][C:14]2=[O:15])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of methyl 2-[({4-[methyl(2-methylquinazolin-4-yl)amino]phenyl}amino)carbonyl]hydrazine carboxylate 0.150 g (0.4 mmol) in THF 5 mL was added K2CO3 0.138 g (1.0 mol), and the reaction mixture was stirred for 48 h under reflux. Due to the incompletion of the reaction, the reaction was further heated under microwave irradiation at 120° C. for 20 min. The reaction mixture was filtrated with a short silica-get column using methanol, and methanol was evaporated under reduced pressure to obtain a crude product, which was purified with preparative HPLC to give the titled compound in pure form. 1H NMR (CD3OD, 400 MHz): δ 8.21, 8.19 (dd, 1H, J=8.0, 1.2 Hz), 7.87-7.83 (m, 2H), 7.79-7.75 (m, 1H), 7.71, 7.69 (dd, 1H, J=8.4, 0.8 Hz), 7.65-7.59 (m, 2H), 7.59-7.53 (m, 1H), 7.30-7.26 (m, 1H), 6.98 (d, 1H, J=8.4 Hz), 3.87 (s, 3H), 2.80 (s, 3H). m/e: 349.30 (M+1), 347.25 (M−1).

Workup

temperatureunder reflux
customDue to the incompletion of the reaction
filtrationThe reaction mixture was filtrated with a short silica-
customget column
customwas evaporated under reduced pressure
customto obtain a crude product, which
customwas purified with preparative HPLC

Sources & evidence

ORD record: ord-391b830acd4e43728f8f1a7042f94a00
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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