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

HRID 1943863Notes

Reaction equation

HRID 1943863 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0b973a95003f41c9a9d666e30e327219
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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