Hydrochloric Acid → HCID 86760798, compound

HRID 2378107Notes

Reaction equation

HRID 2378107 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[CH2:8]([C@H:10]1[CH2:19][C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:24][CH3:25])[N:16]=2)[NH:11]1)[CH3:9].N1C=CC=CC=1.Cl>ClCCl>[CH:5]([O:4][C:2]([N:11]1[C:12]2[C:17](=[N:16][C:15]([O:24][CH3:25])=[CH:14][CH:13]=2)[C@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH2:19][C@@H:10]1[CH2:8][CH3:9])=[O:3])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 86760799HCID 86760799, compound

Product 1

HCID 86760798HCID 86760798, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add isopropyl chloroformate (3.10 mL, 2.82 mmol, 1.0 M in toluene) dropwise to a solution of (+/−)-cis-N-(2-ethyl-6-methoxy-1,2,3,4-tetrahydro-[1,5]naphthyridin-4-yl)acetamide (702 mg, 3.102 mmol) and pyridine (0.677 mL, 8.46 mmol) in dichloromethane (15 mL) at 0° C. under an atmosphere of nitrogen and stir at room temperature for 10 min. Add 1 M HCl and separate the layers. Extract the aqueous layer with dichloromethane. Dry the organic layers over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure, to afford the title compound (895 mg, 95%). MS (ES+): 336 (M+H).

Workup

  1. customseparate the layers
  2. extractionExtract the aqueous layer with dichloromethane
  3. dry with materialDry the organic layers over anhydrous sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-010e5e88f71d45009eac442ea25ab9ff
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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