Triethylamine → 5(R)-hydroxymethyl-3-(4-(4-(5-cyanopyrid-2-yl)piperazin-1-yl)-3-fluorophenyl)-oxazolidin-2-one

HRID 1167421Notes

Reaction equation

HRID 1167421 reaction equation
Cl.[OH:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[C:12]([F:22])[CH:11]=2)[CH2:5]1.C(N(CC)CC)C.Cl[C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][N:32]=1>C(#N)C>[OH:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:17][CH2:18][N:19]([C:31]4[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][N:32]=4)[CH2:20][CH2:21]3)=[C:12]([F:22])[CH:11]=2)[CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 213565653-(3-Fluoro4-(piperazin-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one hydrochloride

Product 1

HCID 112348955(R)-hydroxymethyl-3-(4-(4-(5-cyanopyrid-2-yl)piperazin-1-yl)-3-fluorophenyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5(R)-hydroxymethyl-3-(3-fluoro-4-(piperazin-1-yl)phenyl)oxazolidin-2-one hydrochloride (25 g, 75.4 mmol ) was suspended by stirring in acetonitrile (700 ml) under nitrogen, and triethylamine (16.8 g, 166 mmol ) added, The mixture was stirred for 10 minutes and then 2-chloro-5-cyanopyridine (10.3 g, 75.4 mmol ) added, and the mixture heated under reflux for 18 hours. After cooling, the resultant solid was filtered, washed with water (3×500 ml) and diethyl ether (2×500 ml) to give 5(R)-hydroxymethyl-3-(4-(4-(5-cyanopyrid-2-yl)piperazin-1-yl)-3-fluorophenyl)-oxazolidin-2-one. A further crop was obtained by evaporation of the mother liquors to give a total yield of 23.2 g. MS: ESP+ (M+H)+=398.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. filtrationthe resultant solid was filtered
  5. washwashed with water (3×500 ml) and diethyl ether (2×500 ml)

Sources & evidence

ORD record
ord-dd8e1b94d8b644bf8d3a8c3cc46bedd4
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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