(7R)-7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepine → 6-(4-{1-[(8R)-8-({[t-Butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinonitrile

HRID 1424094ノート

反応式

HRID 1424094 の反応式
[Si:1]([O:8][CH2:9][C@:10]1([CH3:19])[S:16][CH2:15][CH2:14][N:13]=[C:12](SC)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]([C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3([C:37]([NH:39][NH2:40])=O)[CH2:36][CH2:35]3)=[CH:30][CH:29]=2)=[N:26][CH:27]=1)#[N:21]>C(O)CCC>[Si:1]([O:8][CH2:9][C@:10]1([CH3:19])[S:16][CH2:15][CH2:14][N:13]2[C:37]([C:34]3([C:31]4[CH:32]=[CH:33][C:28]([C:25]5[CH:24]=[CH:23][C:22]([C:20]#[N:21])=[CH:27][N:26]=5)=[CH:29][CH:30]=4)[CH2:36][CH2:35]3)=[N:39][N:40]=[C:12]2[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 71466071(7R)-7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepineHCID 867129401-[4-(5-Cyanopyridin-2-yl)phenyl]cyclopropanecarbohydrazide

生成物 1

HCID 867129436-(4-{1-[(8R)-8-({[t-Butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinonitrile収率 54%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
140 °C

実験手順

The compound (418 mg, 1.31 mmol) obtained in Example 4-1) and the compound (364 mg, 1.31 mmol) obtained in Example 60-3) were dissolved in 1-butanol (5 mL), and the mixture was stirred at 140° C. for 5 h under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, then the solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0% to 20%) to obtain the title compound (375 mg, 54%) in a white solid form.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationthe solvent was distilled off
  3. customthe obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0% to 20%)

出典と根拠

ORDレコード
ord-86b617af451148c088b9e2c24007a92b
出典データセット
uspto-grants-2015_01
特許番号
US08927536B2

反応ノート

読み込み中…