Hydrazine hydrate (1:1) → HCID 136385211, compound

HRID 1967918Notes

Reaction equation

[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2C(C3C=CC(CN(C)C)=CC=3)C(=O)[C:18]3[C:17]([C:32]([O:34]C)=O)=[CH:16][CH:15]=[CH:14][C:13]=3[NH:12]2)=[CH:7][CH:6]=1)[CH3:3].[CH3:36][N:37]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([CH:46]2[CH:55](C3C=CC(CN(C)C)=CC=3)C(=O)C3C(C(OCC)=O)=CC=CC=3N2)=[CH:42][CH:41]=1)[CH3:38].O.[NH2:73][NH2:74]>CO>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[NH:12][C:13]3[C:18]4[C:55](=[N:73][NH:74][C:32](=[O:34])[C:17]=4[CH:16]=[CH:15][CH:14]=3)[CH:46]2[C:43]2[CH:42]=[CH:41][C:40]([CH2:39][N:37]([CH3:36])[CH3:38])=[CH:45][CH:44]=2)=[CH:7][CH:6]=1)[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of methyl 2,3-bis(4-((dimethylamino)methyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 2,3-bis(4-((dimethylamino)methyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (165 mg, 0.34 mmol) in hydrazine monohydrate (12 mL) and methanol (5 mL) was stirred at 40° C. for 6 hrs. The mixture was filtered to give crude product. The crude product was purified by prep-HPLC to give 8,9-bis(4-((dimethylamino)methyl)phenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (33.7 mg, yield: 22%) as a light yellow solid. 1H-NMR (400 MHz, CD3OD) δ: 2.04 (s, 6H), 2.05 (s, 6H), 3.19-3.20 (m, 2H), 3.24-3.26 (m, 2H), 4.09-4.11 (d, J=8.8 Hz, 1H), 4.52-4.54 (d, J=8.8 Hz, 1H), 6.88-6.90 (m, 2H), 6.99-7.07 (m, 7H), 7.42-7.46 (m, 2H). LC-MS (ESI) m/z: 454 (M+1)+.

Workup

filtrationThe mixture was filtered
customto give crude product
customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-11e2f16972774a3d9369c6d5bbf40038
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420650B2

Reaction notes

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