Pyridine → HCID 66894164、化合物

HRID 252754ノート

反応式

HRID 252754 の反応式
CS[C:3]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=[CH:4][C:5]#[N:6].[NH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C[CH2:32][N:33](CC)CC>CN(C1C=CN=CC=1)C>[NH2:25][C:30]1[CH:29]=[CH:28][CH:27]=[CH:26][C:32]=1[NH:33][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][NH:14][C:3]([NH:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:5]#[N:6])=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 8471Triethylamine2 回HCID 655264-(Aminomethyl)Benzoic AcidHCID 66893771HCID 66893771、化合物

生成物 1

HCID 66894164HCID 66894164、化合物収率 44%

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

反応条件

温度
55 °C

実験手順

To a mixture of 3-methylsulfanyl-3-(pyridin-4-ylamino)-acrylonitrile (0.2 g, 1.0 mmol), 4-aminomethyl-benzoic acid (0.173 g, 1.14 mmol), DMAP (1 mg) and Et3N (0.14 ml, 1.0 mmol) was added dry pyridine (0.5 ml). The resulting stirring mixture was heated to 55° C. for 4.5 hrs., additional Et3N (0.14 ml) was added and mixture was heated from 75° C. to 90° C. over a period of −30 hrs. When the reaction was complete, pyridine was partially removed in vacuo and the crude was purified by column chromatography (gradient of EtOAc to 20% MeOH/EtOAc) to afford the desired product as an off-white solid (130 mg, 44%).

後処理

  1. temperaturemixture was heated from 75° C. to 90° C. over a period of −30 hrs
  2. custompyridine was partially removed in vacuo
  3. customthe crude was purified by column chromatography (gradient of EtOAc to 20% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-c46ae51ce4c34c0ca830c0e3f00b8208
出典データセット
uspto-grants-2011_01
特許番号
US07868204B2

反応ノート

読み込み中…