6-chloro-2-fluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide → 6-chloro-2-fluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide

HRID 1943960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943960
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]3[C:19]([O:20][CH3:21])=[N:18][N:17](CC4C=CC(OC)=CC=4)[C:14]3=[N:15][CH:16]=2)=[O:9])=[C:6]([F:31])[C:5]([NH:32][S:33]([CH2:36][CH2:37][CH3:38])(=[O:35])=[O:34])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]3[C:19]([O:20][CH3:21])=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)=[O:9])=[C:6]([F:31])[C:5]([NH:32][S:33]([CH2:36][CH2:37][CH3:38])(=[O:35])=[O:34])=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 670888196-chloro-2-fluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide

Produkt 1

HCID 442234716-chloro-2-fluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamideAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

6-Chloro-2-fluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.027 g, 0.0480 mmol) was heated to reflux in TFA overnight. The reaction mixture was cooled to room temperature and was concentrated to an oil. DCM was added to the oil resulting in a precipitate, which was collected by filtration giving 6-chloro-2-fluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.0175 g, 82%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 12.60 (s, 1H), 11.07 (1H, s), 9.99 (br s, 1H), 8.58 (s, 1H), 8.49 (s, 1H), 7.52-7.57 (m, 1H), 7.44-7.46 (m, 1H), 4.02 (s, 3H), 3.15-3.19 (m, 2H), 1.73-1.79 (m, 2H), 0.97-1.01 (m, 3H); m/z (APCI-pos) M+1=442.1.

Aufarbeitung

  1. concentrationwas concentrated to an oil
  2. additionDCM was added to the oil
  3. customresulting in a precipitate, which
  4. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-da6a5c444be746cf975b0ae0388cf01c
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394795B2

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