Pyridine → N-{3-[4-(acetylamino)-2,6-dichlorobenzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide

HRID 875445Notes

Reaction equation

HRID 875445 reaction equation
[NH2:1][C:2]1[CH:24]=[C:23]([Cl:25])[C:5]([C:6]([C:8]2[C:16]3[C:11](=[C:12]([NH:17][C:18]([CH:20]4[CH2:22][CH2:21]4)=[O:19])[N:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[O:7])=[C:4]([Cl:26])[CH:3]=1.N1C=CC=CC=1.[C:33](Cl)(=[O:35])[CH3:34]>ClCCl>[C:33]([NH:1][C:2]1[CH:3]=[C:4]([Cl:26])[C:5]([C:6]([C:8]2[C:16]3[C:11](=[C:12]([NH:17][C:18]([CH:20]4[CH2:21][CH2:22]4)=[O:19])[N:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[O:7])=[C:23]([Cl:25])[CH:24]=1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86720647N-[3-(4-amino-2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide

Product 1

HCID 71061872N-{3-[4-(acetylamino)-2,6-dichlorobenzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamideYield 27.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[3-(4-amino-2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide (0.2 g, 0.5 mmol) in dichloromethane (10 mL), pyridine (0.081 g, 1 mmol) was added followed by addition of acetyl chloride (0.044 g, 0.56 mmol) at 0° C. After stirring at 0° C. for about 0.5 hour, the reaction was kept at room temperature for about 2 hours. Dichloromethane was evaporated; water (50 mL) was added to the reaction mixture, extracted with ethyl acetate (2×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by silica gel (100-200 mesh) column chromatography. Elution with 2.5% methanol in dichloromethane afforded N-{3-[4-(acetylamino)-2,6-dichlorobenzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide (0.06 g, 27%).

Workup

  1. waitthe reaction was kept at room temperature for about 2 hours
  2. customDichloromethane was evaporated
  3. additionwater (50 mL) was added to the reaction mixture
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by silica gel (100-200 mesh) column chromatography
  8. washElution with 2.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-dcbfd91eb3664f519196534d79855285
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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