tert-Butyl piperazine-1-carboxylate → tert-butyl 4-(5-(4-(thiazol-2-ylcarbamoyl)-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 85099ノート

反応式

HRID 85099 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]([NH:19][C:20]4[S:21][CH:22]=[CH:23][N:24]=4)=[O:18])[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[N:25]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CS(C)=O.O>[S:21]1[CH:22]=[CH:23][N:24]=[C:20]1[NH:19][C:17]([C:16]1[C:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:28]4[CH2:27][CH2:26][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29]4)=[N:7][CH:6]=3)[NH:12][C:11]=2[CH:13]=[CH:14][CH:15]=1)=[O:18]

参加物

5

反応物 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 866537852-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide

生成物 1

HCID 86653786tert-butyl 4-(5-(4-(thiazol-2-ylcarbamoyl)-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)piperazine-1-carboxylate収率 71%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A mixture containing 2-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide (7; 30 mg, 0.084 mmol) and tert-butyl piperazine-1-carboxylate (170; 156.5 mg, 0.84 mmol) in DMSO (1.2 mL) was stirred at 140° C. in a microwave reactor for 25 min. The reaction mixture was cooled to room temperature and diluted with water. The resulting solids were collected by filtration, washed with water and dried under vacuum to afford tert-butyl 4-(5-(4-(thiazol-2-ylcarbamoyl)-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)piperazine-1-carboxylate 8 as a pale yellow solid (20 mg, 71%). MS (ESI) calcd for C25H27N7O3S: 505.19; found: 506 [M+H].

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with water
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-b61fc10161cf4f17b7810df374e464d3
出典データセット
uspto-grants-2014_09
特許番号
US08846947B2

反応ノート

読み込み中…