1,2-Dichloroethane → 2-azido-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide

HRID 1875084ノート

反応式

HRID 1875084 の反応式
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:15][CH2:16][C:17]1[C:18]([F:34])=[C:19]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:28]#[N:29])[C:20]([Br:23])=[CH:21][CH:22]=1.[N:35]([C:38]1[NH:39][C:40]([C:44](O)=[O:45])=[C:41]([Cl:43])[N:42]=1)=[N+:36]=[N-:37]>CN(C=O)C.CCOC(C)=O>[N:35]([C:38]1[NH:39][C:40]([C:44]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[C:19]([O:24][C:25]3[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[C:31]([Cl:33])[CH:32]=3)[C:18]=2[F:34])=[O:45])=[C:41]([Cl:43])[N:42]=1)=[N+:36]=[N-:37]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 1785145302-azido-4-chloro-1H-imidazole-5-carboxylic acid

生成物 1

HCID 1785099102-azido-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide収率 103.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

EDC (0.331 g, 1.726 mmol) and HOBT (0.233 g, 1.726 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.558 g, 1.569 mmol) and 2-azido-4-chloro-1H-imidazole-5-carboxylic acid (0.294 g, 1.569 mmol) in DMF (7 mL). The mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc and washed with water and brine and the organic layer was dried over sodium sulfate and concentrated to give the crude title compound (0.850 g) as a light yellow solid. This crude product was taken on to the next step without further purification.

後処理

  1. washwashed with water and brine
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-5f10dc3a15984854be9b11d4dca82415
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

読み込み中…