2-Amino-4-chlorophenol → 5-(5-Chlorobenzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74208

反応式

HRID 74208 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]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1O.CCN=C=NCCCN(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.CN(C=O)C>[Cl:28][C:26]1[CH:25]=[CH:24][C:23]2[O:20][C:18]([C:16]3[CH:15]=[CH:14][C:6]4[N:7]([CH:8]5[CH2:9][CH2:10][O:11][CH2:12][CH2:13]5)[C:3]([CH3:2])=[N:4][C:5]=4[CH:17]=3)=[N:21][C:22]=2[CH:27]=1

参加物

8

反応物 4

HCID 72652-Amino-4-chlorophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 674984452-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

生成物 1

HCID 674980045-(5-Chlorobenzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole収率 15.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt (see Working Example 4-3) (0.25 g, 0.96 mmol), 2-amino-4-chlorophenol (0.15 g, 1.05 mmol), anhydrous DMF (10 mL) and WSC (0.22 g, 1.14 mmol) were stirred overnight at room temperature. After the reaction was complete, water (50 mL) was added, the precipitated crystals were filtered off, and the filter residue was extracted with water/chloroform. After the organic layer was dried over anhydrous sodium sulfate, filtration and concentration gave crystals that were dissolved in toluene (5 mL), to which p-toluenesulfonic acid hydrate (0.32 g, 1.68 mmol) was added and this was stirred at reflux for 2 hours. After the solvent was concentrated at reduced pressure, water (5 mL) was added and the solid obtained was filtered off, and after washing with water, drying at reduced pressure at 50° C. yielded the title compound (54 mg, 15.3% yield) as a light brown solid.

後処理

  1. filtrationthe precipitated crystals were filtered off
  2. extractionthe filter residue was extracted with water/chloroform
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, filtration and concentration
  4. customgave crystals that
  5. additionwas added
  6. temperatureat reflux for 2 hours
  7. concentrationAfter the solvent was concentrated at reduced pressure, water (5 mL)
  8. additionwas added
  9. customthe solid obtained
  10. filtrationwas filtered off
  11. washafter washing with water
  12. customdrying at reduced pressure at 50° C.

出典と根拠

ORDレコード
ord-1c725ea87fce4efa883236e0088e42b4
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

関連ノート

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