Water → HCID 178518770, compound

HRID 521416Notes

Reaction equation

CO[C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[C:15]1[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=1[CH2:13][CH2:12]3)=[CH:8][CH:7]=[CH:6][C:5]=2[C:21](OC)=[O:22].O.[NH2:26][NH2:27].C(OCC)(=O)C.O>CC(N(C)C)=O.[Cl-].[Na+].O>[N:26]1[NH:27][C:21](=[O:22])[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[C:3]=1[C:16]1[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH2:13][CH2:12][C:11]=1[NH:10]3

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of methyl 12-methoxy-5,6-dihydrobenzo[a]acridine-11-carboxylate (20 mg, 0.06 mmol) and hydrazine hydrate (0.5 mL) in DMA (0.8 mL) was heated at 130° C. for 4 h. The reaction mixture was cooled, treated with ethyl acetate (0.5 mL), water (1 mL) and brine (1 mL). The resulting precipitate was collected by filtration, dissolved in a mixture of methanol:dichloromethane (1:8, 10 mL), dried over Na2SO4, filtered, concentrated, chromatographed on silica gel using gradint eluant of 0-3.2% methanol in dichloromethane to give the desired compound as a yellow solid (7 mg, 39%). 1H NMR (DMSO-d6) δ11.85 (s, 1H), 10.88 (s, 1H), 8.77-8.78 (m, 1H), 7.66-7.68 (m, 1H), 7.56-7.57 (m, 1H), 7.35-7.37 (m, 1H), 7.19-7.20 (m, 2H), 7.09-7.11 (m, 1H), 2.83-2.85 (m, 2H), 2.66-2.69 (m, 2H). MS (ESI) m/e [M+1]+288.

Workup

temperatureThe reaction mixture was cooled
filtrationThe resulting precipitate was collected by filtration
dissolutiondissolved in a mixture of methanol:dichloromethane (1:8, 10 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customchromatographed on silica gel using gradint eluant of 0-3.2% methanol in dichloromethane

Sources & evidence

ORD record: ord-9074f54e098144788baaefbc3d3f2b8c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328111B2

Reaction notes

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