Dimethylformamide → HCID 68840988, Verbindung

HRID 229724

Reaktionsgleichung

Reaktionsgleichung von HRID 229724
CN(C)C=O.[CH3:6][CH:7]1[CH2:16][C:15]2[N:14]=[N:13][C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[CH:11][C:10]=2[CH:9]([OH:27])[CH2:8]1.Cl.CN(C)CCCN=C=NCC.[C:40]([O:44][C:45]([NH:47][C@@H:48]([C:56](O)=[O:57])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:46])([CH3:43])([CH3:42])[CH3:41]>C(O)C.C(OCC)(=O)C>[C:40]([O:44][C:45]([NH:47][C@@H:48]([C:56]([O:27][C@H:9]1[CH2:8][C@@H:7]([CH3:6])[CH2:16][C:15]2[N:14]=[N:13][C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[CH:11][C:10]1=2)=[O:57])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:46])([CH3:42])([CH3:43])[CH3:41]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 637610Boc-D-phenylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99725287-Methyl-3-(3-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydrocinnolin-5-ol

Produkt 1

HCID 68840988HCID 68840988, VerbindungAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a N,N-dimethylformamide solution (181 mL) of 7-methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnolin-5-ol (27.8 g, 90.4 mmol) obtained in Example 6 were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (26 g, 135.7 mmol) and N-(tert-butoxycarbonyl)-D-phenylalanine (31.2 g, 117.6 mmol) with washing in N-methylpyrrolidone (36 ml), followed by adding N,N-dimethylaminopyridine (1.2 mg, 9.0 mmol) to the mixed liquid under ice cooling, stirring over night, adding ethyl acetate (0.6 mL) and distilled water (0.3 L) and washing thus extracted organic layer with a 5% by weight aqueous solution of potassium hydrogen sulfate (400 mL), a saturated aqueous solution of sodium bicarbonate (300 mL) and a 10% saline solution (300 mL) sequentially. To residue obtained after concentration of the organic layer was added ethanol (187 mL) and stirred over night at room temperature. Crystal generated was filtered and washed with ethanol (35 mL) to obtain the titled objective compound (14.8 g).

Aufarbeitung

  1. washwith washing in N-methylpyrrolidone (36 ml)
  2. distillationdistilled water (0.3 L)
  3. washwashing thus extracted organic layer with a 5% by weight aqueous solution of potassium hydrogen sulfate (400 mL)
  4. customTo residue obtained after concentration of the organic layer
  5. stirringstirred over night at room temperature
  6. filtrationCrystal generated was filtered
  7. washwashed with ethanol (35 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5b4e3d64f71d407c9b74987f1f6795a6
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563893B2

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