Dimethylamine → HCID 49821537、化合物

HRID 74172ノート

反応式

HRID 74172 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:26]=[CH:25][C:13]2[N:14]([CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:15]([CH2:17]O)=[N:16][C:12]=2[CH:11]=1.C(Cl)(=O)C(Cl)=O.[I-].[Na+].[CH3:35][NH:36][CH3:37]>CN(C)C=O.O1CCCC1.ClCCl>[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:26]=[CH:25][C:13]2[N:14]([CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:15]([CH2:17][N:36]([CH3:37])[CH3:35])=[N:16][C:12]=2[CH:11]=1

参加物

8

反応物 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 65578Oxalyl chlorideHCID 674979855-(Benzoxazol-2-yl)-2-hydroxymethyl-1-(tetrahydropyran-4-yl)benzimidazole

生成物 1

HCID 49821537HCID 49821537、化合物収率 43%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

An eggplant flask (50 mL) equipped with a reflux condenser was charged with 5-(benzoxazol-2-yl)-2-hydroxymethyl-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 13) (0.055 g, 0.16 mmol), oxalyl chloride (0.024 g, 0.19 mmol), and anhydrous dichloromethane (3 mL), and after the addition of anhydrous N,N-dimethylformamide (5 drops) at room temperature, this was refluxed for 3.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. To the yellow residue was added anhydrous tetrahydrofuran (5 mL) and anhydrous sodium iodide (0.036 g, 0.24 mmol), followed by a tetrahydrofuran solution of dimethylamine (2.0 M, 3 mL), and this was refluxed for 14 hours. After being allowed to cool to room temperature, the solvent was distilled off under reduced pressure. The yellow residue (0.70 g) was purified by silica gel column chromatography (silica gel: 2.6 g; MeOH/CHCl3=1/5) to yield the title compound (0.026 g, 43% yield) as a pale yellow powder.

後処理

  1. customAn eggplant flask (50 mL) equipped with a reflux condenser
  2. temperaturethis was refluxed for 3.5 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. temperaturethis was refluxed for 14 hours
  5. temperatureto cool to room temperature
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe yellow residue (0.70 g) was purified by silica gel column chromatography (silica gel: 2.6 g; MeOH/CHCl3=1/5)

出典と根拠

ORDレコード
ord-d2bf71fe33954016a32f5e90f75fc8f9
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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