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

HRID 1943969Notes

Reaction equation

HRID 1943969 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:22][O:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[C:30]([NH2:33])[CH:31]=2)[NH:26][N:25]=1.[CH2:34]([N:36]([C:42]1[C:43]([F:52])=[C:44]([C:48]([F:51])=[CH:49][CH:50]=1)[C:45](O)=[O:46])[S:37](=[O:41])(=[O:40])[NH:38][CH3:39])[CH3:35]>CN(C=O)C.CCOC(C)=O.C(Cl)Cl>[CH2:34]([N:36]([C:42]1[C:43]([F:52])=[C:44]([C:48]([F:51])=[CH:49][CH:50]=1)[C:45]([NH:33][C:30]1[CH:31]=[C:32]2[C:24]([O:23][CH3:22])=[N:25][NH:26][C:27]2=[N:28][CH:29]=1)=[O:46])[S:37](=[O:40])(=[O:41])[NH:38][CH3:39])[CH3:35]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 442236943-Methoxy-1H-pyrazolo[3,4-B]pyridin-5-amineHCID 670525023-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid

Product 1

HCID 670888923-(N-ethyl-N-methylsulfamoylamino)-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamideYield 49%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBt (0.017 g, 0.13 mmol), EDCI (0.054 g, 0.28 mmol), and 3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-amine (0.046 g, 0.28 mmol) was added to 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid (0.075 g, 0.25 mmol) in DMF (1 mL). The reaction mixture was stirred at room temperature for 16 hours. The mixture was diluted with EtOAc (6 mL) and washed with brine (3×5 mL). The organic layers were dried over sodium sulfate, decanted, and concentrated under reduced pressure. The residue was purified via silica gel chromatography eluting with 5% MeOH:DCM to afford 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (0.055 g, 0.12 mmol, 49% yield). 1H NMR (400 MHz, CD3OD) δ 8.60-8.63 (m, 1H), 8.50-8.52 (m, 1H), 7.63-7.70 (m, 1H), 7.09-7.15 (m, 1H), 4.09 (s, 3H), 3.18-3.25 (m, 2H), 2.83 (s, 3H), 1.09-1.14 (m, 3H); m/z (APCI-neg) M−1=439.0.

Workup

  1. washwashed with brine (3×5 mL)
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 5% MeOH

Sources & evidence

ORD record
ord-b413721b93cb45c9bde543c886756968
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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