Hydrochloric Acid → 4-Cyclohept-1-enyl-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinoline-6-carbonitrile

HRID 2053457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053457
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]([C:14]1[O:18][N:17]=[C:16]([CH3:19])[CH:15]=1)=[C:6]2OS(C(F)(F)F)(=O)=O)#[N:2].[C:28]1(B(O)O)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:28]1([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=3)[NH:9][C:8](=[O:13])[C:7]=2[C:14]2[O:18][N:17]=[C:16]([CH3:19])[CH:15]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 3434501Cyclohepten-1-ylboronic acidHCID 136355240Trifluoro-methanesulfonic acid 6-cyano-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinolin-4-yl ester

Produkt 1

HCID 1354400894-Cyclohept-1-enyl-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinoline-6-carbonitrileAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of trifluoro-methanesulfonic acid 6-cyano-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinolin-4-yl ester (30 mg, 0.075 mmol), cyclohepten-1-ylboronic acid (12.6 mg, 0.090 mmol), Pd(PPh3)4 (8.7 mg, 0.0075 mmol) and Na2CO3 (375 ul, 0.75 mmol, 2.0 M) in 1 ml of 1,4-dioxane was stirred at 80° C. for 1 h, then cooled to rt. Treated with 20 ml of H2O, the mixture was acidified to PH=7 with 1N HCl and then extracted with EtOAc (3×15 ml). The combined organic layers were washed with H2O (20 ml), brine (15 ml) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (10-20% EtOAc/DCM) gave 15.1 mg (58%) of product as a white solid: 1H-NMR (CDCl3; 400 MHz) δ 12.3 (s, 1H), 8.08 (d, 1H, J=1.7 Hz), 7.77 (dd, 1H, J=8.6, 1.7 Hz), 7.43 (d, 1H, J=8.6 Hz), 6.70 (s, 1H), 5.79 (t, 1H, J=6.1 Hz), 2.44 (s, 3H), 2.26-2.52 (m, 4H), 1.62-1.94 (m, 6H). Mass spectrum (ESI, m/z): Calcd. for C21H19N3O2, 346.2 (M+H), found 346.1.

Aufarbeitung

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc (3×15 ml)
  3. washThe combined organic layers were washed with H2O (20 ml), brine (15 ml)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-acd1af765af142a09609b1d8ad1214b2
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326788B2

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