Pyridine → HCID 86613810, compound

HRID 2378132Notes

Reaction equation

HRID 2378132 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].N1C=CC=CC=1.[CH:13]([O:16][C:17]([N:19]1[C:28]2[C:23](=[N:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=2)[C@H:22]([NH:31][CH2:32][C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=2)[CH2:21][C@@H:20]1[CH3:47])=[O:18])([CH3:15])[CH3:14]>ClCCl>[CH:13]([O:16][C:17]([N:19]1[C:28]2[C:23](=[N:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=2)[C@H:22]([N:31]([CH2:32][C:33]2[CH:38]=[C:37]([C:39]([F:40])([F:41])[F:42])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=2)[C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:21][C@@H:20]1[CH3:47])=[O:18])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 86613809HCID 86613809, compound

Product 1

HCID 86613810HCID 86613810, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add ethyl chloroformate (0.118 mL, 1.240 mmol), followed by pyridine (0.205 mL, 2.52 mmol), to a solution of (+/−)-cis-4-(3,5-bis-trifluoromethyl-benzylamino)-6-methoxy-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (0.210 g, 0.415 mmol) in dichloromeihane (3 mL). After stirring at room temperature for 12 h remove the solvent in vacuo. Purify using silica gel chromatography, eluting with ethyl acetate/hexane (gradient eluent, 0-30% ethyl acetate in hexane) to afford the title compound (0.218 g, 92%): MS (ES+): 578 (M+H).

Workup

  1. customremove the solvent in vacuo
  2. customPurify
  3. washeluting with ethyl acetate/hexane (gradient eluent, 0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-83d28038e6654c4d86a6e5f4ca54069a
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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