Pyridine → HCID 67112407, compound

HRID 2284296Notes

Reaction equation

HRID 2284296 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH2:7][C:8]1[CH:31]=[CH:30][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1.N1C=CC=CC=1>C(Cl)Cl>[CH:1]1([C:4]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:29])[C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[CH:18][CH:19]=3)=[O:13])=[CH:30][CH:31]=2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 67112462HCID 67112462, compound

Product 1

HCID 67112407HCID 67112407, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of cyclopropanecarbonyl chloride (Aldrich, 448 mg, 4.31 mmol) in 5 mL of methylene chloride was slowly added over 5 minutes to N-(4-(4-aminobenzoyl)phenyl)-4-fluorobenzamide (1.2 g, 3.59 mmol) in 20 mL of methylene chloride containing 3 mL of pyridine. The reaction was stirred at room temperature for 12 h then quenched with 40 mL of water. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organics were washed with 0.5 N HCl (100 mL), brine (100 mL), dried over sodium sulphate, and filtered. Concentration of the organics provided N-(4-(4-(cyclopropanecarboxamido)benzoyl)phenyl)-4-fluorobenzamide (1.3 g, 3.23 mmol) as a tan solid which was used without further purification.

Workup

  1. customthen quenched with 40 mL of water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organics were washed with 0.5 N HCl (100 mL), brine (100 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-6aeed0e743744ba299e8b8afc85c900c
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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