Hydrazine hydrate (1:1) → HCID 136186314, compound

HRID 908009Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17](=O)[C:16]3[C:15]([C:19]([O:21]CC)=O)=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10][CH:9]2[C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.O.[NH2:37][NH2:38]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:17]3=[N:37][NH:38][C:19](=[O:21])[C:15]4[CH:14]=[CH:13][CH:12]=[C:11]([C:16]=43)[NH:10][CH:9]2[C:24]2[CH:25]=[CH:26][C:27]([CH2:30][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:28][CH:29]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of ethyl 3-(4-chlorophenyl)-2-(4-((diethylamino)methyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (268 mg) in 85% hydrazine monohydrate (0.5 mL) and methanol (2 mL) was stirred at 23° C. for overnight. Methanol was removed under reduced pressure. The crude was purified by prep-HPLC to give the title compound (93 mg, yield 37%). LC-MS (ESI) m/z: 459 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.93 (t, 6H), 2.38 (q, 4H), 3.44 (s, 2H), 4.35 (d, 1H), 4.73 (d, 1H), 7.13-7.19 (m, 5H), 7.22-7.25 (m, 4H), 7.38 (d, 2H), 7.41 (s, 1H), 7.56-7.59 (m, 1H).

Workup

customMethanol was removed under reduced pressure
customThe crude was purified by prep-HPLC

Sources & evidence

ORD record: ord-e6554953155348d9875c65a9d7c6ab31
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012976B2

Reaction notes

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