Dichloromethane → N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-8-methyl-2-(2-thienyl)-4-quinolinecarboxamide

HRID 1259847

反応式

HRID 1259847 の反応式
[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl.[CH3:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:34]=1[N:33]=[C:32]([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)[CH:31]=[C:30]2[C:40]([OH:42])=O.[NH2:43][C:44]1[O:45][C:46]([C:49]2[O:50][CH:51]=[CH:52][CH:53]=2)=[N:47][N:48]=1>N1C=CC=CC=1>[O:50]1[CH:51]=[CH:52][CH:53]=[C:49]1[C:46]1[O:45][C:44]([NH:43][C:40]([C:30]2[C:29]3[C:34](=[C:25]([CH3:24])[CH:26]=[CH:27][CH:28]=3)[N:33]=[C:32]([C:35]3[S:36][CH:37]=[CH:38][CH:39]=3)[CH:31]=2)=[O:42])=[N:48][N:47]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 2021855-(Furan-2-yl)-1,3,4-oxadiazol-2-amineHCID 36045198-Methyl-2-(thiophen-2-yl)quinoline-4-carboxylic acidHCID 22470945Triphenylphosphine bromide

生成物 1

HCID 67204226N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-8-methyl-2-(2-thienyl)-4-quinolinecarboxamide収率 12.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Triphenylphosphine bromide (352 mg, 0.80 mmol) was added to a methylene chloride (1 mL) solution of commercially available 8-methyl-2-(2-thienyl)-4-quinolinecarboxylic acid (108 mg, 0.40 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction solution was added to a pyridine (3 mL) solution of 2-amino-5-(2-furyl)-1,3,4-oxadiazole (90.7 mg, 0.60 mmol), and the mixture was stirred at room temperature for 2 hours and then heated with stirring overnight at 60° C. The reaction solution was concentrated. After that, to the residue, water was added, and the deposited solid was collected by filtration, washed with water, dried, and then purified by preparative HPLC to obtain the title compound (22 mg, 0.05 mmol).

後処理

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. temperatureheated
  3. stirringwith stirring overnight at 60° C
  4. concentrationThe reaction solution was concentrated
  5. additionAfter that, to the residue, water was added
  6. filtrationthe deposited solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-baaa908b98d24ca3bb60f5f72697d863
出典データセット
uspto-grants-2013_06
特許番号
US08466290B2

関連ノート

読み込み中…