Acetyl chloride → 2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

HRID 74159

반응식

HRID 74159 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:5]([OH:7])=[O:6].[C:18]([Cl:21])(=O)[CH3:19].O1CCOCC1.Cl>O1CCOCC1>[ClH:21].[CH3:18][C:19]1[N:11]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chloride2회HCID 204431481,4-Dioxane hydrochlorideHCID 548880483-Amino-4-((tetrahydropyran-4-yl)amino)benzoic acid

생성물 1

HCID 674984452-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt수율 93.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매3회

반응 조건

온도
10 °C

실험 절차

3-Amino-4-((tetrahydropyran-4-yl)amino)benzoic acid (see Working Example 4-2) (90 g, 0.38 mol) was dissolved in dioxane (900 mL), and after cooling to 10° C., a solution of acetyl chloride (35.0 g, 0.45 mol) in dioxane (900 mL) was added dropwise over the course of 35 minutes. After heating to reflux with stirring for 2.5 h, another solution of acetyl chloride (15.8 g, 0.20 mol) in dioxane (200 mL) was added to the reaction solution, and this was further heated to reflux with stirring for 3 hours. Next, a 4N HCl dioxane solution (100 mL) was added, and after heating to reflux with stirring for 8 h, this was allowed to cool to room temperature, the solid obtained was filtered off and washed with hexane to yield the title compound (105 g, quant.) as a light purple solid.

후처리

  1. temperatureAfter heating
  2. temperatureto reflux
  3. temperaturethis was further heated
  4. temperatureto reflux
  5. stirringwith stirring for 3 hours
  6. temperatureafter heating
  7. temperatureto reflux
  8. stirringwith stirring for 8 h
  9. temperatureto cool to room temperature
  10. customthe solid obtained
  11. filtrationwas filtered off
  12. washwashed with hexane

출처 및 근거

ORD 기록
ord-c529147e2378423195e9ae0159b4dc6e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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