Thiophene-3-carboxylic acid → HCID 16722644, 화합물

HRID 1983103노트

반응식

HRID 1983103 반응식
[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

참가 물질

5

반응물 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

생성물 1

HCID 16722644HCID 16722644, 화합물수율 51%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-bdd479614fde41d59ca38b4687a81ebd
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07541372B2

반응 노트

불러오는 중…