Tetrahydrofuran → (R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

HRID 132504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132504
[Cl:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][N:12]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:13](=[O:17])[C@H:14]([OH:16])[CH2:15][C:4]=2[CH:3]=1.C1COCC1.[H-].[Na+].[O:30]=[C:31]1[C:40]([CH:41]2[CH2:46][CH2:45][N:44]([C:47](OC3C=CC([N+]([O-])=O)=CC=3)=[O:48])[CH2:43][CH2:42]2)=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32]1>>[O:30]=[C:31]1[C:40]([CH:41]2[CH2:42][CH2:43][N:44]([C:47]([O:16][C@H:14]3[C:13](=[O:17])[N:12]([CH2:18][C:19]([F:21])([F:20])[F:22])[CH2:11][C:5]4[C:6]5[CH:7]=[N:8][NH:9][C:10]=5[C:2]([Cl:1])=[CH:3][C:4]=4[CH2:15]3)=[O:48])[CH2:45][CH2:46]2)=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32]1

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 59732071HCID 59732071, VerbindungHCID 693108914-Nitrophenyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Produkt 1

HCID 11978542(R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylateAusbeute 36,1 %

Versuchsvorschrift

(R)-4-chloro-7-hydroxy-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one (60.0 mg, 0.180 mmol) in THF (10.0 mL, 122 mmol) was added sodium hydride (10.79 mg, 0.450 mmol) followed by 4-nitrophenyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (106 mg, 0.270 mmol). After stirring for 48 h, most of the solvent was removed, diluted with dichloromethane (30 mL) and neutralized with 1.0 M HCl. The organic phase was separated, dried (Na2SO4) and the crude product was purified by flash chromatography using 5% MeOH in dichloromethane to give (R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (38.00 mg, 0.065 mmol, 36% yield). MS (ESI) 588 (M+H); Rf=2.73.

Aufarbeitung

  1. customwas removed
  2. additiondiluted with dichloromethane (30 mL)
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. customthe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9055f6887dbf4eba8f339813bc2f004b
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

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