Ethylamine → HCID 58728142, Verbindung

HRID 1666577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666577
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[S:13]([OH:16])(=O)=[O:14].C(OCC)(=O)C.[CH2:23]([NH2:25])[CH3:24]>C1COCC1>[CH2:23]([NH:25][S:13]([C:8]1[C:9]([F:11])=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:16])=[O:14])[CH3:24]

Komponenten

6

Edukt 4

HCID 6341EthylamineHCID 8857Ethyl AcetateHCID 24638Chlorosulfonic acidHCID 741022,4-Difluorobenzoic acid

Produkt 1

HCID 58728142HCID 58728142, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,4-difluorobenzoic acid (200 mg, 0.765 mmol) in chlorosulfonic acid (1.535 ml, 22.92 mmol) was stirred at room temperature for 30 seconds, then microwave 200 degree for 10 mins. The reaction mixture was cooled to room temperature and dumped on ice (10 g) slowly. Ethyl acetate (25 ml) was added and extracted twice with ethyl acetate (10 mL X2). The combined organic phase was dried over MgSO4. Ethylamine (1833 μl, 3.67 mmol) in THF (2.0 M) was added, stirred at room temperature for 10 mins and washed with 1 N HCl (10 ml). The organic phase was dried over MgSO4 and concentrated to give 5-[(ethylamino)sulfonyl]-2,4-difluorobenzoic acid, which was purified by HPLC 5%-60% CH3CN/H2O TFA (0.1%) to give 60 mg. To 5-[(ethylamino)sulfonyl]-2,4-difluorobenzoic acid in N,N-dimethylformamide (3 ml) and dichloromethane (3 ml) was added to EDC (32.5 mg, 0.170 mmol) and HOBt (26.0 mg, 0.170 mmol). After 10 mins, 5-cyclopentyl-1,3,4-thiadiazol-2-amine was added. The reaction mixture was stirred at rt overnight, concentrated and purifed by HPLC. The solvents were removed and purified by HPLC (30-70% with TFA 0.1% CNCH3 and H2O, 18 mins) to give the title compound (5 mg).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate (10 mL X2)
  2. dry with materialThe combined organic phase was dried over MgSO4
  3. washwashed with 1 N HCl (10 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-98f306162c434536882a6b27a1d5b814
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044075B2

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