Diisopropylethylamine → 1-{4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}-n,n-dimethylazetidine-3-carboxamide

HRID 17421Notes

Reaction equation

HRID 17421 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.[CH:21]([N:24](C(C)C)[CH2:25]C)(C)C.Cl.[NH:31]1[CH2:34][CH:33]([C:35](C[N-]C)=[O:36])[CH2:32]1>ClCCl>[C:19]([C:7]1[C:5]2[N:6]=[C:2]([N:31]3[CH2:32][CH:33]([C:35]([N:24]([CH3:25])[CH3:21])=[O:36])[CH2:34]3)[O:3][C:4]=2[C:10]([F:11])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[CH3:18])#[N:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileHCID 86630847Azetidine-3-carbonyldimethylamide hydrochloride

Product 1

HCID 685852091-{4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}-n,n-dimethylazetidine-3-carboxamideYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.21 g, 0.73 mmol), (diisopropylethylamine (0.28 ml, 1.65 mmol) and azetidine-3-carbonyldimethylamide hydrochloride (I-145) (0.25 g) were dissolved in dichloromethane (10 ml). After heated under reflux for 3 hours, this was diluted with dichloromethane, washed with water, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=100:1) to obtain a colorless oil (0.24 g, 86%)

Workup

  1. temperatureAfter heated
  2. temperatureunder reflux for 3 hours
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=100:1)

Sources & evidence

ORD record
ord-260b37f4f359454690cd8148f2da75b9
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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