1-Hydroxybenzotriazole → HCID 86757751, compound

HRID 1251463Notes

Reaction equation

HRID 1251463 reaction equation
[CH3:1][O:2][C:3]1[C:8](C)=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH:14](C)C(O)=O.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)=[CH:22][CH:21]=1.Cl.CN(C)[CH2:34][CH2:35][CH2:36]N=C=NCC.[OH:43]N1C2C=CC=CC=2N=N1>CN(C=O)C.C(N(CC)CC)C>[N:26]1([C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:34](=[O:43])[CH2:35][CH2:36][C:3]3([O:2][CH3:1])[C:4]([CH3:14])=[C:5]([CH3:13])[C:6]([O:11][CH3:12])=[C:7]([CH3:10])[CH2:8]3)=[CH:25][CH:24]=2)[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 3201654-(1H-imidazol-1-yl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86757752HCID 86757752, compound

Product 1

HCID 86757751HCID 86757751, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2,5-dimethoxy-3,4,6-trimethylphenylpropionic acid (1.91 g), 1-(4-aminophenyl)imidazole(1.35 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(1.63 g) and 1-hydroxybenzotriazole(1.30 g) in DMF (30 ml) was added triethylamine(1.3 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. This solution was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was crystallized from chloroform-ether to obtain N-[4-(imidazol-1-yl)phenyl]-3-(1,4-dimethoxy-3,5,6-trimethylphenyl) propanamide(2.89 g). To a suspension of this amide(1.01 g) and pyridine-2,6-dicarboxylic(1.30 g) in acetonitrile(18 ml) and water(4 ml) was added dropwise cerium ammonium nitrite(4.24 g) in water-acetonitrile(5 ml—5 ml) at 0? with stirring. After the addition was completed, the reaction mixture was stirred for 30 minutes at the same temperature and crystals precipitated were filtered. The crystals were 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=20:1) to obtain the title compound(0.89 g). m.p. 145-150° C.

Workup

  1. filtrationthe precipitate was filtered
  2. dissolutiondissolved in chloroform
  3. washThis solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was crystallized from chloroform-ether

Sources & evidence

ORD record
ord-de9e95bc6efd4e24af8fd7f52c4b1008
Source dataset
uspto-grants-2002_01
Patent number
US06342516B1

Reaction notes

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