Pyridine → HCID 86760803, compound

HRID 2378128Notes

Reaction equation

HRID 2378128 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[CH3:8][O:9][C:10]1[N:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C@@H:15]([CH3:20])[CH2:14][C@H:13]2[NH:21][C:22](=[O:24])[CH3:23].N1C=CC=CC=1>ClCCl>[CH:5]([O:4][C:2]([N:16]1[C:17]2[C:12](=[N:11][C:10]([O:9][CH3:8])=[CH:19][CH:18]=2)[C@H:13]([NH:21][C:22](=[O:24])[CH3:23])[CH2:14][C@@H:15]1[CH3:20])=[O:3])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 86760804HCID 86760804, compound

Product 1

HCID 86760803HCID 86760803, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add isopropyl chloroformate (8.50 mL, 8.50 mmol) to a solution of (+/−)-cis-N-(6-methoxy-2-methyl-1,2,3,4-tetrahydro-[1,5]naphthyridin-4-yl)acetamide (0.404 g, 1.702 mmol), pyridine (1.370 mL, 17.02 mmol) in dichloromethane (10 mL) at 0° C. and slowly warm to room temperature. After 12 h, remove the solvent under reduced pressure. Purify the crude material using silica gel chromatography, eluting with ethyl acetate (neat), to afford the title compound (0.496 g, 91%). MS (ES+): 322 (M+H).

Workup

  1. customremove the solvent under reduced pressure
  2. customPurify the crude material
  3. washeluting with ethyl acetate (neat)

Sources & evidence

ORD record
ord-b3b56a86dc9848f1bc3962bea45ac3de
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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