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

HRID 17324
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HRID 17324 반응식
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]
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참가 물질

7

반응물 4

HCID 8471Triethylamine2회HCID 685846072-Tert-butyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileHCID 68585273HCID 68585273, 화합물2회HCID 86585896Sodium bicarbonate water

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 57417360Sodium chloride; water용매

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a3b1e20a458e4f61b187c78c9c138ede
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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