Sodium ethoxide → N-(3-chlorobenzyl)-9H-benzo[b]pyrido[3,2-f]pyrimido[5,4-d]azepin-2-amine

HRID 1801496Notes

Reaction equation

C(N(/[CH:6]=[C:7]1/[C:8](=O)[C:9]2[CH:21]=[CH:20][CH:19]=[N:18][C:10]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]/1=2)CC)C.[Cl-].[Cl:24][C:25]1[CH:26]=[C:27]([CH:33]=[CH:34][CH:35]=1)[CH2:28][NH:29][C:30]([NH2:32])=[NH2+:31].[O-]CC.[Na+]>C(O)C.ClCCl>[Cl:24][C:25]1[CH:26]=[C:27]([CH:33]=[CH:34][CH:35]=1)[CH2:28][NH:29][C:30]1[N:32]=[CH:6][C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10]3[N:18]=[CH:19][CH:20]=[CH:21][C:9]=3[C:8]=2[N:31]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (E)-6-((diethylamino)methylene)-6,11-dihydro-5H-benzo[f]pyrido[2,3-b]azepin-5-one (0.1 g, 0.38 mmol), 1-(3-chlorobenzyl)guanidinium chloride (2 equivalents), and sodium ethoxide (21% solution in ethanol) (1.9 equivalents) in absolute ethanol (3 mL) was heated at 80° C. overnight. The reaction mixture was cooled and diluted with dichloromethane (10 mL), washed with water (2×5 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash column chromatography (SiO2, 50% ethyl acetate in hexane) to give the pure desired product as solid. 400 MHz 1H NMR (DMSO-d6) δ 8.34 (s, 1H), 8.23 (s, 1H), 8.15 (s, 2H), 8.00 (t, J=6.0 Hz, 1H), 7.42 (s, 1H), 7.37-7.27 (m, 4H), 7.21-7.14 (m, 2H), 7.08-7.04 (m, 2H), 4.57 (d, J=5.2 Hz, 2H); LCMS (M+H)=386.

Workup

temperatureThe reaction mixture was cooled
washwashed with water (2×5 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash column chromatography (SiO2, 50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-61c78ea139394709b9c8899e1f03da4b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349827B2

Reaction notes

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