1-Hydroxybenzotriazole → HCID 15552330, compound

HRID 1251462Notes

Reaction equation

HRID 1251462 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][CH:3]=1.[C:13]1([CH:19]([C:25]2[C:26](=[O:35])[C:27]([CH3:34])=[C:28]([CH3:33])[C:29](=[O:32])[C:30]=2[CH3:31])[CH2:20][CH2:21][C:22](O)=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(N(CC)CC)C>[N:8]1([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:22](=[O:23])[CH2:21][CH2:20][CH:19]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:25]3[C:26](=[O:35])[C:27]([CH3:34])=[C:28]([CH3:33])[C:29](=[O:32])[C:30]=3[CH3:31])=[CH:7][CH:6]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 3201654-(1H-imidazol-1-yl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14651334HCID 14651334, compound

Product 1

HCID 15552330HCID 15552330, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-(4-aminophenyl)imidazole(0.71 g), 4-phenyl 4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)butanoic acid(1.25 g), ,1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(0.85 g) and 1-hydroxybenzotriazole(0.85g) in DMF(8 ml) was added triethylamine(0.7 ml) and the mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into ice water and the precipitate was filtered and dissolved in chloroform-methanol. This solution was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified by column chromatography on silica gel (chloroform: methanol=100:3) to obtain the title compound (0.82 g, amorphous).

Workup

  1. filtrationthe precipitate was filtered
  2. dissolutiondissolved in chloroform-methanol
  3. washThis solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica gel (chloroform: methanol=100:3)

Sources & evidence

ORD record
ord-b6b0a695a45942e5a9d54c07e604412b
Source dataset
uspto-grants-2002_01
Patent number
US06342516B1

Reaction notes

Loading…