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

HRID 1375246

Reaction equation

HRID 1375246 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][CH:46]1[CH:51]([CH3:52])[CH2:50][CH2:49][CH2:48][CH:47]1[NH2:53]>CN(C=O)C>[CH3:45][CH:46]1[CH:51]([CH3:52])[CH2:50][CH2:49][CH2:48][CH:47]1[NH:53][C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:3]2[CH:4]=[C:5]([C:8]3[O:9][C:10]([CH3:13])=[N:11][N:12]=3)[CH:6]=[CH:7][C:2]=2[CH3:1])=[CH:15][CH:16]=1)=[O:21]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1235072,3-DimethylcyclohexylamineHCID 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 21078784N-(2,3-dimethylcyclohexyl)-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-dimethylcyclohexylamine (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-dimethylcyclohexyl)-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide.

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-a123c64c629e48e6b8569cef3f5e7ee5
Source dataset
uspto-grants-2007_01
Patent number
US07166623B2

Linked notes

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