Triethylamine → 2-[(5-Chloro-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2204312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2204312
O(S(C)(=O)=O)S(C)(=O)=O.[CH2:10]([O:12][C:13]([C:15]1[CH:19]=[CH:18][N:17]([CH:20]([CH3:22])[CH3:21])[C:16]=1[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)O)=[O:14])[CH3:11].CCN(CC)CC.[NH2:39][C:40]1[C:41](=[O:48])[N:42]([CH3:47])[CH:43]=[C:44]([Cl:46])[CH:45]=1>C(Cl)Cl.O>[CH2:10]([O:12][C:13]([C:15]1[CH:19]=[CH:18][N:17]([CH:20]([CH3:22])[CH3:21])[C:16]=1[CH:23]([NH:39][C:40]1[C:41](=[O:48])[N:42]([CH3:47])[CH:43]=[C:44]([Cl:46])[CH:45]=1)[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)=[O:14])[CH3:11]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 867031052-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 867031183-Amino-5-chloro-1-methylpyridin-2(1H)-one

Produkt 1

HCID 867031172-[(5-Chloro-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

Ms2O (18.65 mmol) was added at −30° C. to a solution of 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step E4) (9.32 mmol) and Et3N (46.6 mmol) in CH2Cl2 (60 mL) and stirred at −30° C. for 15 min. 3-Amino-5-chloro-1-methyl-1H-pyridin-2-one (Step L4) (11.19 mmol) was added and the mixture was stirred at −10° C. for 30 min. The mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organic phases were washed successively with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography to afford the title compound as a white solid. ESI-MS: tR=1.37 min, [M+]+462/464 (LC-MS 1).

Aufarbeitung

  1. stirringthe mixture was stirred at −10° C. for 30 min
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe combined organic phases were washed successively with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0f943e1bbd13487685a4a2f289a4f81f
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365576B2

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