Thiophene-3-carboxylic acid → HCID 16722644、化合物

HRID 1983103ノート

反応式

HRID 1983103 の反応式
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.Cl.CN(C)CCCN=C=NCC.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH2:46])[CH:26]=[CH:27][C:28]=1[C:29]1[O:30][C:31]([C:34]2[C:35]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[N:36][O:37][C:38]=2[CH3:39])=[N:32][N:33]=1>ClCCl>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH:46][C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[O:8])[CH:26]=[CH:27][C:28]=1[C:29]1[O:30][C:31]([C:34]2[C:35]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[N:36][O:37][C:38]=2[CH3:39])=[N:32][N:33]=1

参加物

5

反応物 3

HCID 6918Thiophene-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167225873-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine

生成物 1

HCID 16722644HCID 16722644、化合物収率 51%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-thiophenecarboxylic acid (162 mg, 1.26 mmol) in dichloromethane (4 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (242 mg, 1.26 mmol). After stirring for 2 min 3-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine (400 mg, 1.15 mmol) was added and stirring was continued for 3 d at ambient temperature. The reaction mixture was extracted with aqueous HCl (1 M, 15 mL) and ethyl acetate (20 mL) and the aqueous layer was extracted with ethyl acetate (20 mL. Drying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=60:20:20 to 0:80:20) afforded the title compound (268 mg, 51%) as a white solid. MS: m/e=459.2 [M+H]+.

後処理

  1. additionwas added
  2. extractionThe reaction mixture was extracted with aqueous HCl (1 M, 15 mL) and ethyl acetate (20 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (20 mL
  4. dry with materialDrying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=60:20:20 to 0:80:20)

出典と根拠

ORDレコード
ord-bdd479614fde41d59ca38b4687a81ebd
出典データセット
uspto-grants-2009_06
特許番号
US07541372B2

反応ノート

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