Hydrochloric Acid → 1-Benzenesulfonyl-5-fluoro-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]-methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

HRID 60223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60223
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([F:16])[CH:14]=2)[N:9]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:8]=1[CH2:26]Br)=[O:6].[C:28]([CH2:30][NH:31][S:32]([C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)(=[O:34])=[O:33])#[N:29].Cl>CN(C=O)C>[CH3:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([F:16])[CH:14]=2)[N:9]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:8]=1[CH2:26][N:31]([CH2:30][C:28]#[N:29])[S:32]([C:35]1[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=1)(=[O:34])=[O:33])=[O:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 3113400N-Cyanomethyl-4-methyl-benzenesulfonamideHCID 583650121-Benzenesulfonyl-5-fluoro-2-bromomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

Produkt 1

HCID 583650531-Benzenesulfonyl-5-fluoro-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]-methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl esterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (1.6 g, 60% dispersion in mineral oil, 40.5 mmol) was added portionwise to a cooled (0° C.) solution of 1-benzenesulfonyl-5-fluoro-2-bromomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (15.8 g, 36.9 mmol) and N-cyanomethyl-4-methyl-benzenesulfonamide (8.5 g, 40.5 mmol) in DMF (150 mL). The reaction mixture was stirred at 0° C. for 15 minutes, then allowed to warm to ambient temperature and stirred for 1 hour. The reaction mixture was poured into a cooled, stirred solution of 2M hydrochloric acid (400 mL). The resultant precipitate was collected by filtration (slow) and the cake washed with water, followed by methanol and then diethyl ether. The resulting cake was dried to afford the title compound as a grey solid (16.7 g, 82%). 1H NMR (400 MHz, DMSO-d6): 8.49 (dd, J=2.8, 1.2 Hz, 1H), 8.24-8.24 (m, 2H), 8.14 (dd, J=8.8, 2.8 Hz, 1H), 7.75-7.74 (m, 1H), 7.70-7.68 (m, 2H), 7.62-7.62 (m, 2H), 7.39-7.35 (m, 2H), 5.36 (s, 2H), 4.42 (s, 2H), 3.88 (s, 3H), 2.36 (s, 3H).

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 1 hour
  3. additionThe reaction mixture was poured into a cooled
  4. filtrationThe resultant precipitate was collected by filtration (slow)
  5. washthe cake washed with water
  6. customThe resulting cake was dried

Quellen und Nachweise

ORD-Eintrag
ord-5c57105e10b34ae0903d8d4da207f217
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440976B2

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