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

HRID 1943863ノート

反応式

HRID 1943863 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[CH:3]=[N:2]1.[F:11][C:12]1[C:20]([NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23])=[CH:19][CH:18]=[C:17]([F:28])[C:13]=1[C:14](O)=[O:15].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[F:11][C:12]1[C:20]([NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:23])=[O:24])=[CH:19][CH:18]=[C:17]([F:28])[C:13]=1[C:14]([NH:10][C:8]1[CH:9]=[C:4]2[CH:3]=[N:2][NH:1][C:5]2=[N:6][CH:7]=1)=[O:15]

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 461929221H-pyrazolo(3,4-b)pyridin-5-amineHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acid

生成物 1

HCID 441994252,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide収率 599.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1H-Pyrazolo[3,4-b]pyridin-5-amine (0.036 g, 0.027 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (0.075 g, 0.27 mmol), EDCI (0.056 g, 0.30 mmol) and HOBt (0.040 g, 0.30 mmol) were dissolved in DMF (8 mL) and stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (200 mL), and the organic layers were washed with water (3×30 mL). The organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (1:1) to give 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (0.064 g, 60%) as a solid. 1H NMR (400 MHz, CD3OD) δ 8.7 (s, 1H), 8.6 (s, 1H), 8.1 (s, 1H), 7.7 (m, 1H), 7.1 (m, 1H), 3.1 (m, 2H), 1.9 (m, 2H), 1.1 (t, J=7.6 Hz, 3H); m/z (APCI-neg) M−1=394.2.

後処理

  1. washthe organic layers were washed with water (3×30 mL)
  2. customThe organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with hexanes/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-0b973a95003f41c9a9d666e30e327219
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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