Triethylamine → 4-(2,3-Difluoro-benzoylamino)-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2249526

Reaktionsgleichung

Reaktionsgleichung von HRID 2249526
[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[F:23][C:24]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[C:9]([NH:11][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:32]([F:33])[C:24]=2[F:23])[CH:10]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 5195492,3-Difluorobenzoyl chlorideHCID 596397164-Amino-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid ethyl ester

Produkt 1

HCID 692874324-(2,3-Difluoro-benzoylamino)-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid ethyl esterAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-amino-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid ethyl ester (1 g, 4.3 mmol) and triethylamine (650 mg, 6.4 mmol) in dry CH2Cl2 (20 mL) was added 2,3-difluoro-benzoyl chloride (760 mg, 4.3 mmol). The mixture was stirred at RT for 3 h and diluted with EtOAc (150 mL). After washing with 2N HCl (80 mL) and NaHCO3 (2×80 mL), the organic layer was dried over MgSO4, filtered, and evaporated to give a yellow solid (1.3 g, 81%). This solid was dried on the vacuum pump for 14 hrs and then was used for the next step directly. MS (ES+): m/e=373.2 (M+H); LC: 3.45 min.

Aufarbeitung

  1. washAfter washing with 2N HCl (80 mL) and NaHCO3 (2×80 mL)
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a2a8d47a122e43349ba57717c69b9894
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314885B2

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