Triethylamine → 3-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-hydroxy methyloxazolidin-2-one

HRID 1167486Notes

Reaction equation

HRID 1167486 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([N:15]2[CH2:19][C@H:18]([CH2:20][OH:21])[O:17][C:16]2=[O:22])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C.Cl[C:31]1[N:32]=[N:33][C:34]([C:37]#[N:38])=[CH:35][CH:36]=1>C(#N)C>[C:37]([C:34]1[N:33]=[N:32][C:31]([N:12]2[CH2:11][CH2:10][N:9]([C:8]3[CH:7]=[CH:6][C:5]([N:15]4[CH2:19][C@H:18]([CH2:20][OH:21])[O:17][C:16]4=[O:22])=[CH:4][C:3]=3[F:2])[CH2:14][CH2:13]2)=[CH:36][CH:35]=1)#[N:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133828716-Chloropyridazine-3-carbonitrileHCID 213565653-(3-Fluoro4-(piperazin-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one hydrochloride

Product 1

HCID 213566023-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-hydroxy methyloxazolidin-2-oneYield 79.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(3-Fluoro4-(piperazin-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one hydrochloride (6.63 g, 20 mmol) was suspended by stirring in acetonitrile (200 ml) under nitrogen, and triethylamine (4.44 g, 44 mmol) added. The mixture was stirred for 10 minutes 3-chloro-6-cyanopyridazine (2.79 g, 20 mmol) added, and the mixture heated under reflux for 18 hours. After cooling, solid was filtered, washed with water (3×150 ml) and diethyl ether (2×150 ml) to give the title product (6.3 g).

Workup

  1. additionadded
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 18 hours
  4. temperatureAfter cooling
  5. filtrationsolid was filtered
  6. washwashed with water (3×150 ml) and diethyl ether (2×150 ml)

Sources & evidence

ORD record
ord-6c3aaccc63d046c18199c444e79d67df
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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