(+-)-p-Methoxyamphetamine → N-[2-(4-methoxyphenyl)-1-methylethyl]-2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-4-carboxamide

HRID 131739노트

반응식

HRID 131739 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]([OH:22])=O)=[CH:16][CH:15]=1.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH:54]([NH2:56])[CH3:55])=[CH:49][CH:48]=1>CN(C=O)C>[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH:54]([NH:56][C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:3]3[CH:4]=[C:5]([C:8]4[O:9][C:10]([CH3:13])=[N:11][N:12]=4)[CH:6]=[CH:7][C:2]=3[CH3:1])=[CH:15][CH:16]=2)=[O:22])[CH3:55])=[CH:49][CH:48]=1

참가 물질

6

반응물 4

HCID 31721(+-)-p-MethoxyamphetamineHCID 757711-HydroxybenzotriazoleHCID 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 10138206N-[2-(4-methoxyphenyl)-1-methylethyl]-2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-4-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2′-Methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (11.3 mg, 0.034 mmol), HOBT (6.0 mg, 0.044 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (8.0 mg, 0.042 mmol) and 2-(4-methoxyphenyl)-1-methylethylamine (0.34 mmol) were mixed in DMF (0.7 ml) and the reaction left at room temperature for 18 h. The DMF was evaporated under vacuum and the residue partitioned between DCM (0.4 ml) and water (0.4 ml). The organic phase was washed with aqueous sodium hydroxide (0.5M, 0.2 ml) and the DCM evaporated under vacuum. The residue was purified by mass directed HPLC to give N-[2-(4-methoxyphenyl)-1-methylethyl]-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide. LCMS; retention time 3.41 min, MH+ 442.

후처리

  1. customThe DMF was evaporated under vacuum
  2. customthe residue partitioned between DCM (0.4 ml) and water (0.4 ml)
  3. washThe organic phase was washed with aqueous sodium hydroxide (0.5M, 0.2 ml)
  4. customthe DCM evaporated under vacuum
  5. customThe residue was purified by mass

출처 및 근거

ORD 기록
ord-e5addb2d14c94a53a97b3128b54db14c
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384963B2

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