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

HRID 1943964Notes

Reaction equation

HRID 1943964 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.[Cl:11][C:12]1[C:17]([C:18](O)=[O:19])=[C:16]([F:21])[C:15]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:14][CH:13]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:11][C:12]1[C:17]([C:18]([NH:10][C:8]2[CH:9]=[C:4]3[CH:3]=[N:2][NH:1][C:5]3=[N:6][CH:7]=2)=[O:19])=[C:16]([F:21])[C:15]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 461929221H-Pyrazolo[3,4-b]pyridin-5-amineHCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acid

Product 1

HCID 573950146-chloro-2-fluoro-3-(propylsulfonamido)-N-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzamideYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-Pyrazolo[3,4-b]pyridin-5-amine (1.55 g, 11.6 mmol), 6-chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (3.59 g, 12.1 mmol), EDCI (2.44 g, 12.7 mmol), and HOBt (0.25 g, 0.16 mmol) were dissolved in DMF (30 mL) and stirred at room temperature for 16 hours. The reaction mixture was concentrated. The residue was diluted with ethyl acetate (500 mL), and the organic layers were washed with water (3×50 mL). The organic layers were dried, filtered and concentrated. The crude solids were washed with DCM (3×50 mL) to give 6-chloro-2-fluoro-3-(propylsulfonamido)-N-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (2.7 g, 58%) 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), 7.4 (m, 1H), 3.1 (m, 2H), 1.9 (m, 2H), 1.1 (t, J=7.6 Hz, 3H); m/z (APCI-neg) M−1=410.2, 412.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was diluted with ethyl acetate (500 mL)
  3. washthe organic layers were washed with water (3×50 mL)
  4. customThe organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe crude solids were washed with DCM (3×50 mL)

Sources & evidence

ORD record
ord-f6ef0cb3a9244b1b8276d58ac7ea1f86
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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