Hydrochloric Acid → HCID 22632924, compound

HRID 2416822Notes

Reaction equation

HRID 2416822 reaction equation
[CH:1]1([NH:4][C:5]2[C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][C:8]([F:16])=[C:7]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[N:6]=2)[CH2:3][CH2:2]1.[OH-].[Na+].CO.Cl>O.C1COCC1>[CH:1]1([NH:4][C:5]2[C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]([F:16])=[C:7]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[N:6]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 22633001HCID 22633001, compound

Product 1

HCID 22632924HCID 22632924, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-cyclopropylamino-5-fluoro-6-pyrrolidinyl-3-pyridine-carboxylate (Example E-2, 270 mg, 0.92 mmol) and NaOH (360 mg, 9.0 mmol) in water (1 mL), THF (2 mL), and MeOH (1 mL) was refluxed for 3 hours. The mixture was cooled to room temperature, acidified with dilute HCl to pH 6, and evaporated under reduced pressure. The residue was mixed with 10% MeOH/dichloromethane (40 mL), dried on sodium sulfate, filtered, and evaporated. The solid residue was further washed with hexane and dried in vacuo, giving 215 mg of the title compound as powder, mp 64-66° C.

Workup

  1. customwas refluxed for 3 hours
  2. customevaporated under reduced pressure
  3. additionThe residue was mixed with 10% MeOH/dichloromethane (40 mL)
  4. customdried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. washThe solid residue was further washed with hexane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-4bb49e6e6e5f46a48be7cc81659580c2
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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