Hydrochloric Acid → HCID 68681493, compound

HRID 2353953Notes

Reaction equation

HRID 2353953 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[CH3:8][O:9][C:10](=[O:19])[C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:18].N1C=CC=CC=1.Cl>ClCCl>[CH3:8][O:9][C:10](=[O:19])[C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[NH:18][C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 2818492Methyl 2-amino-6-fluorobenzoate

Product 1

HCID 68681493HCID 68681493, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add isopropyl chloroformate (20.7 mL, 20.7 mmol, 1.0 M in toluene) dropwise to a solution of 2-Amino-6-fluor-benzoic acid methyl ester (3.5 g, 20.7 mmol) and pyridine (4.2 mL, 51.75 mmol) in dichloromethane (41 mL) at 0° C. under an atmosphere of nitrogen and stir at room temperature for 14 h. Add 1M HCl and separate the layers. Extract the aqueous layer with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (3.00 g, 63%). MS (ES+): 256 (M+H).

Workup

  1. customseparate the layers
  2. extractionExtract the aqueous layer with dichloromethane
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under reduced pressure
  6. customPurify the residue by flash chromatography
  7. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-226d8cd37f9a4bb5bb2871abe154998f
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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