Diethyl Pyrocarbonate → 4-(1H-Imidazol-2-yl)-N-((1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)benzamide

HRID 735774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735774
Cl.[CH3:2][O:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH2:26])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1.C(N(CC)CC)C.[NH:34]1[CH:38]=[CH:37][N:36]=[C:35]1[C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1.CCOC(OC(OCC)=O)=O>O1CCCC1.O>[NH:34]1[CH:38]=[CH:37][N:36]=[C:35]1[C:39]1[CH:40]=[CH:41][C:42]([C:43]([NH:26][C@@H:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]2[C:18]([N:17]2[C@@H:13]3[C@@H:14]([C@H:5]([CH2:4][O:3][CH3:2])[NH:6][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=43)[CH2:15][CH2:16]2)=[O:19])=[O:44])=[CH:46][CH:47]=1

Komponenten

7

Edukt 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 14759014-(1H-imidazol-2-yl)benzoic AcidHCID 67150575(1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride

Produkt 1

HCID 578470834-(1H-Imidazol-2-yl)-N-((1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)benzamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (200 mg, 0.480 mmol) in tetrahydrofuran (5 ml) were added triethylamine (0.199 ml, 1.44 mmol), 4-(1H-imidazol-2-yl)benzoic acid (99.0 mg, 0.529 mmol) and DEPC (0.079 ml, 0.529 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The obtained residue was subjected to column chromatography using silica gel and eluted with ethyl acetate-methanol (1:0-4:1) to give the title compound (150 mg, 61%) as an amorphous form.

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate-methanol (1:0-4:1)

Quellen und Nachweise

ORD-Eintrag
ord-9a0c3b08a45f4a538664a3bb0eb3a12e
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592453B2

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