1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67155879, compound

HRID 2196668Notes

Reaction equation

HRID 2196668 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[N:4]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:3]=1.[F:21][C:22]1[C:30]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33])=[CH:29][CH:28]=[C:27]([F:38])[C:23]=1[C:24](O)=[O:25].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:21][C:22]1[C:30]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:33])=[O:34])=[CH:29][CH:28]=[C:27]([F:38])[C:23]=1[C:24]([NH:11][C:8]1[CH:9]=[C:10]2[C:2]([I:1])=[CH:3][N:4]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1)=[O:25]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidHCID 66887603HCID 66887603, compound

Product 1

HCID 67155879HCID 67155879, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine (0.506 g, 1.27 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (0.389 g, 1.39 mmol), EDCI (0.267 g, 1.39 mmol) and HOBt (0.188 g, 1.39 mmol) were dissolved in DMF (10 mL) and stirred at room temperature overnight. The organic portion was washed with water (3×), brine, dried over Na2SO4 and concentrated. The resulting residue was purified by column chromatography (1:1:1 hexane/Et2O/DCM) giving 2,6-difluoro-N-(3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.738 g, 88.2%).

Workup

  1. washThe organic portion was washed with water (3×), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by column chromatography (1:1:1 hexane/Et2O/DCM)

Sources & evidence

ORD record
ord-634d5b0ef72a420182c075f0aa8c6d40
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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