Hydrochloric Acid → 5-(3-{[2,6-difluoro-3-(propane-1-sulfonylamino)-phenyl]-hydroxy-methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamide

HRID 217621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217621
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[CH:20]=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][N:7]=1)=[O:5])[CH3:2].[F:21][C:22]1[C:27]([CH:28]=[O:29])=[C:26]([F:30])[CH:25]=[CH:24][C:23]=1[NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33].[OH-].[K+].Cl>CO>[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:20]([CH:28]([C:27]4[C:26]([F:30])=[CH:25][CH:24]=[C:23]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33])[C:22]=4[F:21])[OH:29])=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][N:7]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 53419003N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamideHCID 595696015-(1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamide

Produkt 1

HCID 595696145-(3-{[2,6-difluoro-3-(propane-1-sulfonylamino)-phenyl]-hydroxy-methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamideAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In a round bottom flask, 5-(1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamide (38, 71 mg, 0.27 mmol), propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (58, 84.2 mg, 0.32 mmol) and potassium hydroxide (44.9 mg, 0.80 mmol) were combined with 1.1 mL of methanol. The reaction was stirred for 2 hours at room temperature. The reaction solution was neutralized with 0.1 N hydrochloric acid, then extracted 3× with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting residue was purified by silica gel column chromatography to provide the desired compound (73, 55 mg). MS (ESI) [M+H+]+=530.1.

Aufarbeitung

  1. extractionextracted 3× with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7289de66ed9644bab68d35e4c0b6af28
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198273B2

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