Morpholine → 7-Fluoro-5-methyl-2-morpholin-4-yl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17570Notes

Reaction equation

HRID 17570 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[C:17]1[O:18][C:19]2[C:20](=[C:22]([C:34]#[N:35])[C:23]([CH3:33])=[C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:25]=2[F:26])[N:21]=1>ClCCl>[F:26][C:25]1[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:23]([CH3:33])[C:22]([C:34]#[N:35])=[C:20]2[C:19]=1[O:18][C:17]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[N:21]2

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685844347-Fluoro-5-methyl-2-morpholin-4-yl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With cooling with ice, morpholine (36 μl, 0.413 mmol) and diisopropylethylamine (140 μl, 0.825 mmol) were added to a dichloromethane (3 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenylbenzoxazole-4-carbonitrile (I-130) (99 mg, 0.344 mmol), followed by stirring at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure, then the resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (115 mg, 99%) as a white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-2f41c7d599524283aa54e4eb7bbf9c52
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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