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

HRID 74168

반응식

HRID 74168 반응식
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

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
160 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-70fa3b5a46054bdbaa14858d5fd3d388
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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