HCID 22048857, compound → HCID 10255488, compound

HRID 1275198Notes

Reaction equation

HRID 1275198 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:7][CH2:6]1.[N+](C1C=CC([O:30][C:31]([N:33]2[CH:37]([C:38]3[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([F:45])[CH:39]=3)[CH2:36][O:35][C:34]2=[O:46])=O)=CC=1)([O-])=O>C1COCC1>[CH3:20][O:19][C:17](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:31]([N:33]2[CH:37]([C:38]3[CH:39]=[C:40]([F:45])[CH:41]=[C:42]([F:44])[CH:43]=3)[CH2:36][O:35][C:34]2=[O:46])=[O:30])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 22048857HCID 22048857, compoundHCID 229935851-(3-Amino-propyl)-4-(2-carbomethoxyphenyl)-piperazine

Product 1

HCID 10255488HCID 10255488, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-amino-propyl)-4-(2-carbomethoxyphenyl)-piperazine (25 mg, 0.090 mmol) in 10 mL of THF, 4-(3,5-difluorophenyl)-2-oxo-oxazolidine-3-carboxylic acid-4-nitro-phenyl ester(30 mg, 0.082 mmol) was added and the resulting yellow solution was stirred under argon atmosphere for 2 h at room temperature. The solvent was removed in vacuo and the residue was purified by column chromatography over silica gel with 1:1 hexane/EtOAc followed by 1:9 MeOH/EtOAc (Rf =0.75, MeOH/EtOAc=1:3) to obtain 2-[4-(3-{[4-(3,5-difluoro-phenyl)-2-oxo-oxazolidine-3-carbonyl]-amino}-propyl)-piperazin-1-yl]-benzoic acid methyl ester (31 mg, 69%). The compound was dissolved in CH2Cl2 (3 mL) and was treated with 1N HCl in ether (1 mL). The solvent was removed in vacuo to give the corresponding hydrochloride salt as a yellow solid. M. P. 93-96° C.; [α]D =+45.3, (c=0.29, MeOH); Anal. Calcd. For C25H30N4O5F2Cl2.0.58 CH2Cl2 : C, 50.48; H, 5.16; N, 9.20. Found: C, 50.46; H, 5.56; N,8.91.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography over silica gel with 1:1 hexane/EtOAc

Sources & evidence

ORD record
ord-e373649cb1bf402e955eb4c371ae8df2
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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