Acetyl chloride → HCID 71584841, Verbindung

HRID 1257274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257274
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]3[C:17]([Cl:34])=[CH:18][C:19]([F:33])=[C:20]([NH:22][C:23]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=4)=[O:24])[CH:21]=3)[C:8](=[O:15])[N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][N:3]=1.[C:35](Cl)(=[O:37])[CH3:36]>N1C=CC=CC=1>[Cl:34][C:17]1[CH:18]=[C:19]([F:33])[C:20]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[O:24])=[CH:21][C:16]=1[C:7]1[C:8](=[O:15])[N:9]([CH:12]([CH3:14])[CH3:13])[C:10]2[C:5]([CH:6]=1)=[CH:4][N:3]=[C:2]([NH:1][C:35](=[O:37])[CH3:36])[CH:11]=2

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 86713691HCID 86713691, Verbindung

Produkt 1

HCID 71584841HCID 71584841, VerbindungAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 1-(5-(7-amino-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-chloro-2-fluorophenyl)-3-(3-fluorophenyl)urea (0.07 g, 0.145 mmol) in pyridine (2 mL) was treated with acetyl chloride (0.011 mL, 0.159 mmol) and stirred at RT for 2 h. The mixture was concentrated to dryness, treated with EtOAc, washed with brine, dried over Na2SO4 and concentrated to dryness. The material was treated with Et2O and the solid collected via filtration to afford N-(3-(2-chloro-4-fluoro-5-(3-(3-fluorophenyl)ureido)phenyl)-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)acetamide (65 mg, 84% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.81 (s, 1H), 9.31 (s, 1H), 8.78 (s, 1H), 8.68 (s, 1H), 8.54 (s, 1H), 8.18 (d, J=8.6 Hz, 1H), 7.93 (s, 1H), 7.58 (d, J=11.0 Hz, 1H), 7.46 (dt, J=11.9, 2.3 Hz, 1H), 7.29 (m, 1H), 7.06 (m, 1H), 6.79 (td, J=8.5, 2.6 Hz, 1H), 5.36 (m, 1H), 2.14 (s, 3H), 1.56 (d, J=7.0 Hz, 6H); MS (ESI) m/z: 526.1 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness
  2. additiontreated with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. additionThe material was treated with Et2O
  7. filtrationthe solid collected via filtration

Quellen und Nachweise

ORD-Eintrag
ord-48d103c057fd4f64a671a1394a4aa8a6
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461179B1

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