1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,6-difluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide

HRID 1943892ノート

反応式

HRID 1943892 の反応式
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([NH2:12])[CH:10]=2)[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:4]=1.[F:22][C:23]1[C:31]([NH:32][S:33]([CH2:36][CH2:37][CH3:38])(=[O:35])=[O:34])=[CH:30][CH:29]=[C:28]([F:39])[C:24]=1[C:25](O)=[O:26].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:22][C:23]1[C:31]([NH:32][S:33]([CH2:36][CH2:37][CH3:38])(=[O:34])=[O:35])=[CH:30][CH:29]=[C:28]([F:39])[C:24]=1[C:25]([NH:12][C:9]1[CH:10]=[C:11]2[C:3]([O:2][CH3:1])=[N:4][N:5]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:6]2=[N:7][CH:8]=1)=[O:26]

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 670888713-Methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-amine

生成物 1

HCID 670888582,6-difluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide収率 13.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-amine (0.0118 g, 0.0414 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (0.0127 g, 0.0455 mmol), EDCI (0.00873 g, 0.0455 mmol), and HOBt (0.00615 g, 0.0455 mmol) were dissolved in DMF (1.5 mL) and stirred overnight at room temperature. The solution was partitioned between water and EtOAc. The organic layer was washed with water (3×), brine, dried over Na2SO4 and concentrated to an oil, which was purified by column chromatography (4:1 to 3:2 hexane/EtOAc to give 2,6-difluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.003 g, 13.3%) as an oil.

後処理

  1. customThe solution was partitioned between water and EtOAc
  2. washThe organic layer was washed with water (3×), brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to an oil, which
  5. customwas purified by column chromatography (4:1 to 3:2 hexane/EtOAc

出典と根拠

ORDレコード
ord-eccfe4e037ff420a8d0a69d1f22d1e98
出典データセット
uspto-grants-2013_03
特許番号
US08394795B2

反応ノート

読み込み中…