Triethylamine → 3,4-dimethoxyphenyl 2-[(2-aminophenyl)carbamoyl]-1-methyl-1,4,5,7-tetrahydro-6H-pyrrolo[2,3-c]pyridine-6-carboxylate

HRID 2093111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093111
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[N:19]([CH3:20])[C:14]2[CH2:15][NH:16][CH2:17][CH2:18][C:13]=2[CH:12]=1)=[O:10].CCN(CC)CC.[N+](C1C=CC([O:37][C:38](=O)[O:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[C:42]([O:48][CH3:49])[CH:41]=2)=CC=1)([O-])=O>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[N:19]([CH3:20])[C:14]2[CH2:15][N:16]([C:38]([O:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[C:42]([O:48][CH3:49])[CH:41]=3)=[O:37])[CH2:17][CH2:18][C:13]=2[CH:12]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 44203072Carbonic acid 3,4-dimethoxy-phenyl ester 4-nitro-phenyl esterHCID 66864727N-(2-aminophenyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

Produkt 1

HCID 668652443,4-dimethoxyphenyl 2-[(2-aminophenyl)carbamoyl]-1-methyl-1,4,5,7-tetrahydro-6H-pyrrolo[2,3-c]pyridine-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(2-aminophenyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (1.0 eq) obtained in step IX of example 228, in DMF was added Et3N (3.0 eq.) followed by carbonic acid 3,4-dimethoxy-phenyl ester 4-nitro-phenyl ester (1.0 eq) and stirred at room temperature overnight. Reaction mixture was then quenched with water and extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the title compound.

Aufarbeitung

  1. customReaction mixture
  2. customwas then quenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude product, which
  7. customon purification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7e2e5b542fa048cd9c872931e68f34bf
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440830B2

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