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

HRID 1875251ノート

反応式

HRID 1875251 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.[Br:35][C:36]1[N:37]=[CH:38][NH:39][C:40]=1[C:41](O)=[O:42]>CN(C=O)C>[Br:35][C:36]1[N:37]=[CH:38][NH:39][C:40]=1[C:41]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[C:19]([O:24][C:25]2[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:18]=1[F:34])=[O:42]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 1785249144-bromo-1H-imidazole-5-carboxylic acid

生成物 1

HCID 1785099064-bromo-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide収率 45.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (0.059 g, 0.309 mmol) and HOBT (0.042 g, 0.309 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.100 g, 0.281 mmol) and 4-bromo-1H-imidazole-5-carboxylic acid (0.054 g, 0.281 mmol) in DMF (2 ml). The mixture was stirred at RT overnight. The reaction mixture was extracted with ethyl acetate and saturated aqueous sodium bicarbonate and the organic layer was dried over sodium sulfate and concentrated. Purification by reverse phase HPLC (acetonitrile:water with 0.1% formic acid) gave 0.068 g (45%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.34 (br. s., 1H), 7.77 (s, 2H), 7.58 (d, 1H), 7.45 (s, 1H), 7.40 (t, 1H), 7.27 (t, 1H), 4.45 (d, 2H). ES MS: m/z 527 (M+1).

後処理

  1. extractionThe reaction mixture was extracted with ethyl acetate and saturated aqueous sodium bicarbonate
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by reverse phase HPLC (acetonitrile:water with 0.1% formic acid)

出典と根拠

ORDレコード
ord-aa4658bbf3914063afc5981facc299f5
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…