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

HRID 17324
ノート
印刷プレビュー

反応式

HRID 17324 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 685846072-Tert-butyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileHCID 68585273HCID 68585273、化合物2 回HCID 86585896Sodium bicarbonate water

生成物 1

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

試薬・触媒・溶媒

2
HCID 679Dimethyl Sulfoxide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a3b1e20a458e4f61b187c78c9c138ede
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

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