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 1943892Notes

Reaction equation

HRID 1943892 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eccfe4e037ff420a8d0a69d1f22d1e98
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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