Dichloromethane → 7-Fluoro-5-methyl-2-(4-methyl-3-oxopiperazin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17474Notes

Reaction equation

HRID 17474 reaction equation
C(N(C(C)C)CC)(C)C.Cl.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][C:13]1=[O:18].ClCCl.Cl[C:23]1[O:24][C:25]2[C:26](=[C:28]([C:40]#[N:41])[C:29]([CH3:39])=[C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:31]=2[F:32])[N:27]=1>C(Cl)(Cl)Cl>[F:32][C:31]1[C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:29]([CH3:39])[C:28]([C:40]#[N:41])=[C:26]2[C:25]=1[O:24][C:23]([N:15]1[CH2:16][CH2:17][N:12]([CH3:11])[C:13](=[O:18])[CH2:14]1)=[N:27]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 170607661-Methylpiperazin-2-one--hydrogen chloride (1/1)HCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685845617-Fluoro-5-methyl-2-(4-methyl-3-oxopiperazin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 99.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Diisopropylethylamine (232 μl, 1.36 mmol) and 1-methylpiperazin-2-one hydrochloride (103 mg, 0-682 mmol) were added to a dichloromethane (6 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (163 mg, 0.569 mmol), followed by stirring at room temperature for 30 minutes. Chloroform (50 ml) was added to the reaction liquid, followed by washing with saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=20:1) to obtain the entitled compound (207 mg, 99.9%) as a colorless solid.

Workup

  1. washby washing with saturated brine (50 ml)
  2. dry with materialAfter drying over anhydrous sodium sulfate and concentration under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-8aee05eaa86143319375b494e6912907
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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