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

HRID 131743Notes

Reaction equation

HRID 131743 reaction equation
[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.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[CH3:45][O:46][C:47]1[CH:48]=[C:49]([CH2:55][CH:56]([NH2:58])[CH3:57])[CH:50]=[CH:51][C:52]=1[O:53][CH3:54]>CN(C=O)C>[CH3:45][O:46][C:47]1[CH:48]=[C:49]([CH2:55][CH:56]([NH:58][C:20]([C:17]2[CH:16]=[CH:15][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:19][CH:18]=2)=[O:21])[CH3:57])[CH:50]=[CH:51][C:52]=1[O:53][CH3:54]

Participants

6

Reactant 4

HCID 8423(+-)-3,4-DimethoxyamphetamineHCID 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

Product 1

HCID 10140147N-[2-(3,4-dimethoxyphenyl)-1-methylethyl]-2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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-(3,4-dimethoxyphenyl)-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-(3,4-dimethoxyphenyl)-1-methylethyl]-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide. LCMS; retention time 3.23 min, MH+ 472.

Workup

  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

Sources & evidence

ORD record
ord-e4b7c2efac2244e9bf13fc3a826eb0ba
Source dataset
uspto-grants-2008_06
Patent number
US07384963B2

Reaction notes

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