1H-1,2,4-Triazole → HCID 69216383, compound

HRID 2221820Notes

Reaction equation

HRID 2221820 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH2:38]C)=[C:9]([CH2:11][O:12][C:13]2[CH:35]=[CH:34][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[CH:25]/[CH2:26]O)=[CH:22][N:21]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:20]=3)=[CH:15][C:14]=2[O:36][CH3:37])[N:10]=1.C(P(CCCC)CCCC)CCC.[NH:53]1[CH:57]=[N:56][CH:55]=[N:54]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:38])=[C:9]([CH2:11][O:12][C:13]2[CH:35]=[CH:34][C:16]([CH2:17][O:18][C:19]3[C:23]([CH:24]([N:53]4[CH:57]=[N:56][CH:55]=[N:54]4)[CH:25]=[CH2:26])=[CH:22][N:21]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:20]=3)=[CH:15][C:14]=2[O:36][CH3:37])[N:10]=1

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 69215106HCID 69215106, compound

Product 1

HCID 69216383HCID 69216383, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (2E)-3-{3-[(4-{[2-(2-furyl)-5-ethyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-2-propen-1-ol (1.00 g), tributylphosphine (0.77 g), 1H-1,2,4-triazole (0.26 g) and tetrahydrofuran (30 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.95 g) at room temperature, and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 1-(1-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-2-propenyl)-1H-1,2,4-triazole as crystals (0.48 g, yield 45%) from a fraction eluted with ethyl acetate-hexane (2:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° C.

Workup

  1. customThe precipitated crystals were removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ecfc0f97d29c491bbb65831f0ba4064f
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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