Water → HCID 86721377, compound

HRID 869544Notes

Reaction equation

HRID 869544 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:16]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17]1.O>ClCCl>[F:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:20]([CH:16]2[CH2:19][CH2:18][CH2:17]2)=[O:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 8194405-Amino-2-fluoropyridine

Product 1

HCID 86721377HCID 86721377, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[step 1] 6-Fluoropyridin-3-amine (600 mg, 5.35 mmol) was dissolved in dichloromethane (20 mL), triethylamine (1.49 mL, 10.7 mmol) and cyclobutanecarbonyl chloride (0.67 mL, 5.89 mmol) were added, and the mixture was stirred at room temperature overnight. Water was added to the mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue was added diisopropyl ether and the precipitated crystals were collected by suction filtration to give N-(6-fluoropyridin-3-yl)cyclobutanecarboxamide (899 mg, 86%).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionTo the obtained residue was added diisopropyl ether
  5. filtrationthe precipitated crystals were collected by suction filtration

Sources & evidence

ORD record
ord-de63990bc1344bd3933dd001d446fd44
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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