1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

HRID 389990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389990
C(N(CC)C(C)C)(C)C.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][C:11]1=[O:16].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:38]([C:40]1[C:56]([F:57])=[CH:55][C:43]([O:44][C:45]2[CH:53]=[CH:52][C:48]([C:49](O)=[O:50])=[CH:47][C:46]=2[F:54])=[C:42]([O:58][CH3:59])[CH:41]=1)[CH3:39].C(=O)([O-])O.[Na+]>ClCCl>[CH2:38]([C:40]1[C:56]([F:57])=[CH:55][C:43]([O:44][C:45]2[CH:53]=[CH:52][C:48]([C:49]([N:13]3[CH2:14][CH2:15][NH:10][C:11](=[O:16])[CH2:12]3)=[O:50])=[CH:47][C:46]=2[F:54])=[C:42]([O:58][CH3:59])[CH:41]=1)[CH3:39]

Komponenten

8

Edukt 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 516892Sodium BicarbonateHCID 671160464-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid

Produkt 1

HCID 671162484-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

N,N-Diisopropylethylamine (2.8 mL, 16 mmol), piperazin-2-one (780 mg, 7.8 mmol), EDCI (1.5 g, 7.8 mmol) and HOBt (1.05 g, 7.8 mmol) were successively added to a solution of 4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid (which may be prepared in accordance with the experimental described in Example 4, step 4; 2.0 g, 6.5 mmol) in dichloromethane (22 mL). The reaction mixture was stirred at room temperature overnight and then diluted by addition of dichloromethane (50 mL) and a saturated solution of sodium hydrogen carbonate (50 mL). After separation, the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel, using dichloromethane/petroleum ether (80/20) to dichloromethane (100%) to dichloromethane/methanol (98:2 to 95:5) as eluent. The title product was obtained as a yellow solid (2.0 g, 80%).

Aufarbeitung

  1. custommay be prepared in accordance with the
  2. customAfter separation
  3. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-df76e572cbd54892a100dbf86fb037fd
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383621B2

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