Ammonia → 5-(Benzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74168

反応式

HRID 74168 の反応式
Cl.[CH3:2][C:3]1[N:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:6]2[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:5]=2[N:4]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1O.N>>[O:20]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:18]1[C:16]1[CH:15]=[CH:14][C:6]2[N:7]([CH:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[C:3]([CH3:2])=[N:4][C:5]=2[CH:17]=1

参加物

4

反応物 3

HCID 222AmmoniaHCID 58012-AminophenolHCID 674984452-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

生成物 1

HCID 498213825-(Benzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole収率 0.2%

反応条件

温度
160 °C

実験手順

An eggplant flask (100 mL) was charged with 2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt (see Working Example 4-3) (0.64 g, 2.46 mmol), 2-aminophenol (0.32 g, 2.95 mmol) and polyphosphoric acid (approx. 18 g), and this was heated to 160° C. and stirred for 17 hours. After being allowed to cool, ice was added and concentrated aqueous ammonia (28%) was added to the liquid to give approx. pH 9. This was extracted with chloroform (approx. 50 mL, 3 times) and dried over anhydrous magnesium sulfate. The crude product (0.08 g) obtained after the solvent was distilled off was purified by PTLC (CHCl3) with double development to yield the title compound (0.002 g, 0.2% yield) as a yellowish-brown semisolid.

後処理

  1. temperatureto cool
  2. additionice was added
  3. customto give approx. pH 9
  4. extractionThis was extracted with chloroform (approx. 50 mL, 3 times)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe crude product (0.08 g) obtained after the solvent
  7. distillationwas distilled off
  8. customwas purified by PTLC (CHCl3) with double development

出典と根拠

ORDレコード
ord-70fa3b5a46054bdbaa14858d5fd3d388
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

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