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
Reaction equation
[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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- customThe reaction mixture was directly purified by reverse phase HPLC
Sources & evidence
- ORD record
- ord-ac8414464aef4d69850f303065933fe6
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338452B2
Reaction notes
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