1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178461064、化合物

HRID 1943914ノート

反応式

HRID 1943914 の反応式
[CH3:1][C@H:2]1[CH2:4][C@H:3]1[C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[NH:7][N:6]=1.[F:15][C:16]1[C:24]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])=[CH:23][CH:22]=[C:21]([F:32])[C:17]=1[C:18](O)=[O:19].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:15][C:16]1[C:24]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])=[CH:23][CH:22]=[C:21]([F:32])[C:17]=1[C:18]([NH:14][C:11]1[CH:12]=[C:13]2[C:5]([C@@H:3]3[CH2:4][C@@H:2]3[CH3:1])=[N:6][NH:7][C:8]2=[N:9][CH:10]=1)=[O:19]

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 178461433HCID 178461433、化合物

生成物 1

HCID 178461064HCID 178461064、化合物収率 69.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-(cis-2-Methylcyclopropyl)-1H-pyrazolo[3,4-b]pyridin-5-amine (0.0399 g, 0.212 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (0.0651 g, 0.233 mmol), EDCI (0.0488 g, 0.254 mmol), and HOBt (0.0344 g, 0.254 mmol) were dissolved in DMF 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 (1:2 hexanes/EtOAc) to give 2,6-difluoro-N-(3-((1R,2S)-2-methylcyclopropyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (66 mg, 69%) as a solid. 1H NMR (400 MHz, d6-DMSO) 13.16 (s, 1H), 11.07 (s, 1H), 9.81 (s, 1H), 8.63 (s, 1H), 8.55 (s, 1H), 7.53-7.59 (m, 1H), 7.26-7.31 (m, 1H), 3.11-3.15 (m, 2H), 1.99-2.03 (m, 1H), 1.75-1.80 (m, 2H), 1.32-1.34 (m, 1H), 1.14-1.22 (m, 3H) 0.99-1.02 (m, 3H), 0.78-0.83 (m, 3H); m/z (APCI-pos) M+1=450.1.

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 (1:2 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-9ccdbad9e2874ef797c7951278d0d812
出典データセット
uspto-grants-2013_03
特許番号
US08394795B2

反応ノート

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