Chlorosuccinimide → 8-((2-amino-2,4-dimethylpentyl)oxy)-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398394
C(OC(=O)[NH:7][C:8]([CH3:32])([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:23]3[C:18](=[C:19]([CH3:24])[N:20]=[CH:21][CH:22]=3)[C:17](=[O:25])[N:16]([CH3:26])[C:15]=2[CH:27]=1)(C)(C)C.C1C(=O)N([Cl:41])C(=O)C1>C(#N)C>[NH2:7][C:8]([CH3:32])([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:9][O:10][C:11]1[C:12]([Cl:41])=[CH:13][C:14]2[C:23]3[C:18](=[C:19]([CH3:24])[N:20]=[CH:21][CH:22]=3)[C:17](=[O:25])[N:16]([CH3:26])[C:15]=2[CH:27]=1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 89957266Tert-butyl(1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamate

Produkt 1

HCID 732140208-((2-amino-2,4-dimethylpentyl)oxy)-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-oneAusbeute 13,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To the stirred solution of 8-((2-amino-2,4-dimethylpentyl)oxy)-4,6 dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (Prepared in Example 32, Part B) (0.08 g, 0.226 mmol) in acetonitrile (5 mL) was added NCS (0.030 g, 0.226 mmol)) at RT and the reaction mixture was stirred for 2 h. The mixture was then evaporated to dryness. The residue was purified by reverse phase HPLC (0.1% TFA in water/AcCN) to afford 8-((2-amino-2,4-dimethylpentyl)oxy)-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (12 mg, 0.030 mmol, 13% yield). LC/MS (ESI) m/e 388.0 [(M+H)+, calcd for C21H27ClN3O2, 388.2] as an off-white solid. LC/MS retention time (method C): tR=2.13 min. HPLC retention time (method A): tR=8.97 min; HPLC retention time (method B): tR=10.16 min. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.99-1.02 (m, 6H), 1.30 (s, 3H), 1.54-1.66 (m, 2H), 1.84-1.90 (m, 1H), 3.05 (s, 1H), 3.73 (s, 1H), 4.04 (q, J=23.20 Hz, 2H), 7.03 (s, 1H), 8.06 (d, J=6.00 Hz, 1H), 8.39 (s, 1H), 8.54 (d, J=6.00 Hz, 1H).

Aufarbeitung

  1. customThe mixture was then evaporated to dryness
  2. customThe residue was purified by reverse phase HPLC (0.1% TFA in water/AcCN)

Quellen und Nachweise

ORD-Eintrag
ord-99323c73ed73492e9f9ae7e807da7b5a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901305B2

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