Dimethylformamide → HCID 178521750、化合物

HRID 454684ノート

反応式

HRID 454684 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].CN(C)C=O.[CH2:12]([O:19][C:20]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:39][C:21]=1[C:22]([NH:24][C:25]1[CH:26]=[C:27]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[CH:29][C:30]=1[C:31]#[N:32])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.C(Cl)(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:39][C:21]=1[C:22]([NH:24][C:25]1[CH:26]=[C:27]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[CH:29][C:30]=1[C:31]1[NH:32][N:3]=[N:2][N:1]=1)=[O:23])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium Chloride4 回HCID 33557Sodium Azide4 回HCID 66990791HCID 66990791、化合物

生成物 1

HCID 178521750HCID 178521750、化合物収率 66.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
110 °C

実験手順

Sodium azide (0.065 g) and ammonium chloride (0.053 g) were added to an N,N-dimethylformamide (2.5 mL) suspension of 2-(benzyloxy)-N-(4-cyanobiphenyl-3-yl)-5-(piperidin-1-yl)benzamide (0.25 g), followed by stirring at 110° C. for 2 hours. The reaction mixture was cooled to room temperature, and then sodium azide (0.065 g) and ammonium chloride (0.053 g) were added thereto, followed by stirring at 110° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then sodium azide (0.032 g) and ammonium chloride (0.026 g) were added thereto, followed by stirring at 110° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then sodium azide (0.032 g) and ammonium chloride (0.026 g) were added thereto, followed by stirring at 110° C. for 1 hour. The reaction mixture was cooled to room temperature, and then chloroform and water were added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] and then purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-93% chloroform/methanol] to obtain 0.18 g of 2-(benzyloxy)-N-(5-phenyl-2-(1H-tetrazol-5-yl)phenyl)-5-(piperidin-1-yl)benzamide as a brown solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring at 110° C. for 1 hour and 30 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. stirringby stirring at 110° C. for 1 hour and 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. stirringby stirring at 110° C. for 1 hour
  7. temperatureThe reaction mixture was cooled to room temperature
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]
  12. custompurified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-93% chloroform/methanol]

出典と根拠

ORDレコード
ord-6f06526c6fae431bb65b9057f2d8c0af
出典データセット
uspto-grants-2013_07
特許番号
US08492582B2

反応ノート

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