Acetaldehyde → 2-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74215ノート

反応式

HRID 74215 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][C:9]=2[NH2:10])[CH2:3][CH2:2]1.[CH:24](=O)[CH3:25].OOS([O-])=O.[K+].[C:33](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:24][C:25]1[N:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[C:8]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[C:20]([CH3:33])[C:18]=4[N:19]=3)=[CH:11][C:9]=2[N:10]=1

参加物

7

反応物 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

生成物 1

HCID 674988722-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole収率 20.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 46-2) (0.56 g, 1.7 mmol) in dimethylformamide (5 mL) containing water (0.18 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 90 mg, 1.8 mmol) and oxone (0.69 mg, 1.1 mmol), and this was stirred at room temperature for 3 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (123 mg, 20.4% yield) as light brown crystals.

後処理

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-764065c8d4984caeb5f455023038785f
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

反応ノート

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