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

HRID 2196741
Notes
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Reaction equation

HRID 2196741 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH:22]1[C:26]2=[N:27][CH:28]=[C:29]([NH2:31])[CH:30]=[C:25]2[CH:24]=[CH:23]1.[CH2:32]([N:34]([C:40]1[C:41]([F:50])=[C:42]([C:46]([F:49])=[CH:47][CH:48]=1)[C:43](O)=[O:44])[S:35](=[O:39])(=[O:38])[NH:36][CH3:37])[CH3:33]>CN(C=O)C.CCOC(C)=O>[CH2:32]([N:34]([C:40]1[C:41]([F:50])=[C:42]([C:46]([F:49])=[CH:47][CH:48]=1)[C:43]([NH:31][C:29]1[CH:30]=[C:25]2[CH:24]=[CH:23][NH:22][C:26]2=[N:27][CH:28]=1)=[O:44])[S:35](=[O:38])(=[O:39])[NH:36][CH3:37])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineHCID 670525023-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid

Product 1

HCID 671564383-(N-ethyl-N-methylsulfamoylamino)-2,6-difluoro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamideYield 7.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBt (0.011 g, 0.085 mmol), EDCI (0.036 g, 0.19 mmol), and 1H-pyrrolo[2,3-b]pyridin-5-amine (0.025 g, 0.19 mmol) was added to 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid (0.050 g, 0.17 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-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.005 g, 0.012 mmol, 7.2% yield). m/z (APCI-neg) M−1=408.0.

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-DCM

Sources & evidence

ORD record
ord-46cad1514c254d8ba3ef4bd1d5243730
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08338452B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes