Diglycolamine → HCID 71618424, compound

HRID 875451Notes

Reaction equation

HRID 875451 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[CH:7][CH:8]=[C:9]2[C:13]([C:14]([C:16]3[C:24]([Cl:25])=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][C:17]=3[Cl:26])=[O:15])=[CH:12][NH:11][C:10]=12)(=[O:3])[CH3:2].[NH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][OH:33].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O>[C:1]([NH:4][C:5]1[N:6]=[CH:7][CH:8]=[C:9]2[C:13]([C:14]([C:16]3[C:17]([Cl:26])=[CH:18][C:19]([C:20]([NH:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][OH:33])=[O:22])=[CH:23][C:24]=3[Cl:25])=[O:15])=[CH:12][NH:11][C:10]=12)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 13578DiglycolamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 71061368HCID 71061368, compound

Product 1

HCID 71618424HCID 71618424, compoundYield 29.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichlorobenzoic acid (0.1 g, 0.25 mmol) was taken in a reaction vial. To it 2-(2-aminoethoxy)ethanol (0.029 g, 2.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.073 g, 3.8 mmol), 1-hydroxybenzotriazole (0.051 g, 3.8 mmol) and dimethylformamide (2 mL) were added. The whole reaction mixture was stirred at room temperature for overnight. Water (20 mL) was added to the reaction mixture, extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to get the crude mass which was purified by flash column chromatography to get 4-{[7-(acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-[2-(2-hydroxyethoxy)ethyl]benzamide (0.035 g, 29%).

Workup

  1. customThe whole reaction mixture
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto get the crude mass which
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-e4109372c36647ab8e0d291a493c788d
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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