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

HRID 1875084노트

반응식

HRID 1875084 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5f10dc3a15984854be9b11d4dca82415
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

반응 노트

불러오는 중…