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 2196720ノート

反応式

HRID 2196720 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ac8414464aef4d69850f303065933fe6
出典データセット
uspto-grants-2012_12
特許番号
US08338452B2

反応ノート

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