Hydrazine hydrate (1:1) → 4-(8-(4-Fluorophenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-9-yl)-N,N-dimethylbenzamide

HRID 1968068Notes

Reaction equation

[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:20](=O)[C:19]3[C:18]([C:22](OCC)=[O:23])=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][CH:12]2[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:7][CH:6]=1)=[O:4].O.[NH2:36][NH2:37]>CO>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH:12]2[NH:13][C:14]3[C:19]4[C:20](=[N:36][NH:37][C:22](=[O:23])[C:18]=4[CH:17]=[CH:16][CH:15]=3)[CH:11]2[C:8]2[CH:9]=[CH:10][C:5]([C:3]([N:2]([CH3:1])[CH3:34])=[O:4])=[CH:6][CH:7]=2)=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of ethyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (400 mg, 0.87 mmol) and hydrazine monohydrate (85%, 10 mL) were dissolved in MeOH (20 mL), and stirred at 35° C. for 2 h. The mixture was concentrated under reduced pressure. The resulting mixture was filtered, the solid was washed with water and methanol to obtain a white solid, and the solid was dried in vacuum at 40° C. to obtain the title compound (100 mg, yield 54%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.85 (s, 3H), 2.94 (s, 3H), 4.37-4.40 (d, 1H), 4.80-4.82 (d, 1H), 7.17-7.25 (m, 5H), 7.33-7.36 (m, 2H), 7.39-7.41 (d, 1H), 7.45 (s, 1H), 7.57-7.61 (t, 1H), 12.19 (s, 1H); LC-MS (ESI) m/z: 429 (M+1)+.

Workup

concentrationThe mixture was concentrated under reduced pressure
filtrationThe resulting mixture was filtered
washthe solid was washed with water and methanol
customto obtain a white solid
customthe solid was dried in vacuum at 40° C.

Sources & evidence

ORD record: ord-cacdc2572aca480fa764678cb12b4745
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420650B2

Reaction notes

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