1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(3-fluoropropylsulfonamido)benzamide

HRID 2196720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196720
[CH3:1][C:2]1[NH:11][C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[C:3]=1[CH3:12].[F:13][C:14]1[C:22]([NH:23][S:24]([CH2:27][CH2:28][CH2:29][F:30])(=[O:26])=[O:25])=[CH:21][CH:20]=[C:19]([F:31])[C:15]=1[C:16](O)=[O:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:1][C:2]1[NH:11][C:5]2=[N:6][CH:7]=[C:8]([NH:10][C:16](=[O:17])[C:15]3[C:19]([F:31])=[CH:20][CH:21]=[C:22]([NH:23][S:24]([CH2:27][CH2:28][CH2:29][F:30])(=[O:25])=[O:26])[C:14]=3[F:13])[CH:9]=[C:4]2[C:3]=1[CH3:12]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 580953432,6-Difluoro-3-(3-fluoropropylsulfonamido)benzoic acidHCID 671560582,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine

Produkt 1

HCID 67156459N-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(3-fluoropropylsulfonamido)benzamideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,3-Dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine (0.048 g, 0.298 mmol), 2,6-difluoro-3-(3-fluoropropylsulfonamido)benzoic acid (0.097 g, 0.328 mmol), EDCI (0.063 g, 0.328 mmol) and HOBt (0.040 g, 0.298 mmol) were dissolved in DMF (1.6 mL) and stirred at room temperature for 16 hours. The reaction mixture was directly purified by reverse phase HPLC to give N-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(3-fluoropropylsulfonamido)benzamide (0.043 g, 33%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 11.24 (s, 1H), 10.80 (s, 1H), 9.93 (br s, 1H), 8.18 (d, 2H), 7.61-7.46 (m, 1H), 7.35-7.19 (m, 1H), 4.68-4.56 (m, 1H), 4.56-4.44 (m, 1H), 3.29-3.16 (m, 2H), 2.32 (s, 3H), 2.23-2.04 (m, 5H); m/z (ES-MS) 441.1 (98.2%) [M+1]. One methyl peak was hidden under solvent signal.

Aufarbeitung

  1. customThe reaction mixture was directly purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ac8414464aef4d69850f303065933fe6
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338452B2

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