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

HRID 1943959노트

반응식

HRID 1943959 반응식
[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.[Cl:22][C:23]1[C:28]([C:29](O)=[O:30])=[C:27]([F:32])[C:26]([NH:33][S:34]([CH2:37][CH2:38][CH3:39])(=[O:36])=[O:35])=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:22][C:23]1[C:28]([C:29]([NH:12][C:9]2[CH:10]=[C:11]3[C:3]([O:2][CH3:1])=[N:4][N:5]([CH2:13][C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)[C:6]3=[N:7][CH:8]=2)=[O:30])=[C:27]([F:32])[C:26]([NH:33][S:34]([CH2:37][CH2:38][CH3:39])(=[O:36])=[O:35])=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acidHCID 670888713-Methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-amine

생성물 1

HCID 670888196-chloro-2-fluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide수율 68.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-amine (0.020 g, 0.070 mmol), 6-chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (0.023 g, 0.077 mmol), EDCI (0.015 g, 0.077 mmol), and HOBt (0.010 g, 0.077 mmol) were dissolved in DMF (1.0 mL) and stirred for two days at room temperature. The solution was partitioned between water and EtOAc. The organic layers were washed with water (3×), brine, dried over Na2SO4 and concentrated to an oil. The residue was purified by column chromatography (2:1 hexanes/EtOAc) giving 6-chloro-2-fluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.027 g, 68%) as a solid.

후처리

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

출처 및 근거

ORD 기록
ord-d16e1beea59e446686e52b8d8303315a
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394795B2

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