Potassium Carbonate → 5-(Benzoxazol-2-yl)-2-(2-phenylethynyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74239

反応式

HRID 74239 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[C:24]1([C:30]#[C:31][CH:32]=O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:32]([C:31]#[C:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:15][C:14]=2[CH:16]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 75740PhenylpropynalHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

生成物 1

HCID 674981115-(Benzoxazol-2-yl)-2-(2-phenylethynyl)-1-(tetrahydropyran-4-yl)benzimidazole収率 49%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (38.0 mg, 0.119 mmol) in dimethylformamide (2 mL) was added phenylpropargylaldehyde (ca. 90%, 22.6 μL, 0.360 mmol) and oxone (73.2 mg, 0.119 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 (20.0 mg, 49% yield) as pale yellow 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-a14adcba51f9401dbf1a8df79e19e20e
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

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