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 1943959Notes

Reaction equation

HRID 1943959 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.[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d16e1beea59e446686e52b8d8303315a
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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