Aniline → 2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-N-phenyl-1,1'-biphenyl-4-carboxamide

HRID 131669

반응식

HRID 131669 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][C:3]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH:18][CH:19]=1

참가 물질

6

반응물 3

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 112201194-[2-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzoic Acid

생성물 1

HCID 101336892'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-N-phenyl-1,1'-biphenyl-4-carboxamide수율 51%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

2′-Methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (50 mg, 0.17 mmol), aniline (16 mg, 0.17 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (33 mg, 0.17 mmol) and DMF (20 drops) were suspended in dry DCM (5 ml) and stirred at room temperature under nitrogen for 4 h. The mixture was absorbed onto an SPE (silica, 10 g), eluted with DCM and then with a DCM/ethanol/ammonia gradient (250:8:1 to 100:8:1). The solvent was evaporated from the product fractions under vacuum to yield 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-N-phenyl-1,1′-biphenyl-4-carboxamide as a white solid (32 mg, 51%). NMR; δH [2H6]—DMSO 10.34,(1H, b), 8.06,(2H, d), 7.91,(1H, dd), 7.80,(3H, m), 7.57,(3H, m), 7.36,(2H, t), 7.11,(1H, t), 2.57,(3H, s), 2.34,(3H, s). LCMS; retention time 3.39 min, MH+ 370.

후처리

  1. customThe mixture was absorbed onto an SPE (silica, 10 g)
  2. washeluted with DCM
  3. customThe solvent was evaporated from the product fractions under vacuum

출처 및 근거

ORD 기록
ord-bde7d17d9f534e3ab93e7fb604307e36
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384963B2

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