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

HRID 2196721ノート

反応式

HRID 2196721 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][CH3:29])(=[O:26])=[O:25])=[CH:21][CH:20]=[C:19]([F:30])[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:30])=[CH:20][CH:21]=[C:22]([NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[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 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidHCID 671560582,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine

生成物 1

HCID 67155730N-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide収率 47%

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-propylsulfonamido)benzoic acid (0.092 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-(propylsulfonamido)benzamide (0.059 g, 47%) as a solid. 1H NMR (400 MHz, d6-DMSO) 11.23 (s, 1H), 10.77 (s, 1H), 9.19 (br s, 1H), 8.27-8.09 (m, 2H), 7.59-7.39 (m, 1H), 7.28-7.10 (m, 1H), 3.17-2.95 (m, 2H), 2.32 (s, 3H), 2.15 (s, 3H), 1.84-1.65 (m, 2H), 0.98 (s, 3H); m/z (ES-MS) 423.2 (96.1%) [M+1].

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-4c6b9293e7504e0197043d56e2a0b796
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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