Triethylamine → HCID 70204681, compound

HRID 1595234Notes

Reaction equation

HRID 1595234 reaction equation
[C:1]([C:3]1[C:4](F)=[C:5]([F:22])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][C:8]2=[O:21])#[N:2].Cl.Cl.[NH2:26][CH2:27][C:28]12[CH2:35][NH:34][CH2:33][CH:32]1[CH2:31][CH2:30][O:29]2.C(N(CC)CC)C>C(#N)C>[NH2:26][CH2:27][C:28]12[CH2:35][N:34]([C:4]3[C:3]([C:1]#[N:2])=[C:12]4[C:7]([C:8](=[O:21])[CH:9]=[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:11]4[CH:13]4[CH2:15][CH2:14]4)=[CH:6][C:5]=3[F:22])[CH2:33][CH:32]1[CH2:31][CH2:30][O:29]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21704750HCID 21704750, compoundHCID 21704752HCID 21704752, compound

Product 1

HCID 70204681HCID 70204681, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

350 mg (1.21 mmol) of ethyl 8-cyano-1-cyclopropyl-6,7-difluoro-1,4-dihydro4-oxo-quinolinecarboxylate and 260 mg (1.2 mmol) of (1SR,5RS)-1-aminomethyl-2-oxa-7-azabicyclo[3.3.0]octane dihydrochloride in 30 ml of absolute acetonitrile are admixed with 470 mg (4.64 mmol) of triethylamine and stirred at room temperature overnight. The mixture is concentrated and the residue is purified chromatographically (silica gel; dichloromethane/methanol 9:1). 450 mg (86% of theory) of ethyl 7-([1SR,5RS]-1-aminomethyl-2-oxa-7-azabicyclo[3.3.0]oct-7-yl)-8-cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinolinecarboxylate are isolated, melting point: 193° C.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is purified chromatographically (silica gel; dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-56996141cb754ed2870d654a0ab30bb9
Source dataset
uspto-grants-2001_09
Patent number
US06288081B1

Reaction notes

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