Triethylamine → 2-tert-Butyl-5-methyl-7-(3-methylaminoazetidin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17324Notes

Reaction equation

HRID 17324 reaction equation
C(N(CC)CC)C.FC(F)(F)C(O)=O.Cl.[CH3:16][NH:17][CH:18]1[CH2:21][NH:20][CH2:19]1.[C:22]([C:26]1[O:27][C:28]2[C:29](=[C:31]([C:43]#[N:44])[C:32]([CH3:42])=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:34]=2F)[N:30]=1)([CH3:25])([CH3:24])[CH3:23].O.C(=O)(O)[O-].[Na+]>[Cl-].[Na+].O.CS(C)=O>[C:22]([C:26]1[O:27][C:28]2[C:29](=[C:31]([C:43]#[N:44])[C:32]([CH3:42])=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:34]=2[N:20]2[CH2:21][CH:18]([NH:17][CH3:16])[CH2:19]2)[N:30]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 68584607HCID 68584607, compoundHCID 68585273HCID 68585273, compound2×HCID 86585896Sodium bicarbonate water

Product 1

HCID 685840002-tert-Butyl-5-methyl-7-(3-methylaminoazetidin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 69.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

Triethylamine (316 μl, 2.27 mmol) and 3-methylaminoazetidine hydrochloride trifluoroacetate (140 mg, 590 μmol) were added to a dimethyl sulfoxide (3.5 ml) solution of 2-tert-butyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-72) (140 mg, 454 μmol), followed by stirring overnight at 90° C., then 3-methylaminoazetidine hydrochloride trifluoroacetate (53.7 mg, 227 μmol) and triethylamine (63.3 μl, 454 μmol) were added, followed by stirring at 90° C. for 8 hours. After cooling, saturated sodium bicarbonate water and saturated brine were added to the reaction liquid, and this was extracted with ethyl acetate and chloroform. The organic layers were combined, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol-100:1) to obtain the entitled compound (118 mg, 69%) as a pale yellow solid.

Workup

  1. stirringby stirring at 90° C. for 8 hours
  2. temperatureAfter cooling
  3. extractionthis was extracted with ethyl acetate and chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol-100:1)

Sources & evidence

ORD record
ord-a3b1e20a458e4f61b187c78c9c138ede
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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