Methanamine, N-methoxy-, hydrochloride (1:1) → (2E)-3-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-N-methoxy-N-methyl-2-propenamide

HRID 2221859Notes

Reaction equation

HRID 2221859 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[O:12][C:13]([CH3:44])=[C:14]([CH2:16][O:17][C:18]2[CH:41]=[CH:40][C:21]([CH2:22][O:23][C:24]3[C:28](/[CH:29]=[CH:30]/[C:31](O)=[O:32])=[CH:27][N:26]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:25]=3)=[CH:20][C:19]=2[O:42][CH3:43])[N:15]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>O.C(N(CC)CC)C.CN(C)C=O>[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[O:12][C:13]([CH3:44])=[C:14]([CH2:16][O:17][C:18]2[CH:41]=[CH:40][C:21]([CH2:22][O:23][C:24]3[C:28](/[CH:29]=[CH:30]/[C:31]([N:3]([O:4][CH3:5])[CH3:2])=[O:32])=[CH:27][N:26]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:25]=3)=[CH:20][C:19]=2[O:42][CH3:43])[N:15]=1

Participants

8

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69215034(2E)-3-{3-[(4-([2-(2-furyl)-5-methyl-4-oxazolyl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-2-propenoic acid

Product 1

HCID 86605810(2E)-3-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-N-methoxy-N-methyl-2-propenamideYield 88.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of N,O-dimethylhydroxylamine hydrochloride (0.56 g) and N,N-dimethylformamide (30 mL) was added triethylamine (0.69 g) at room temperature, and the mixture was stirred for 15 min. To the reaction mixture were added (2E)-3-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-2-propenoic acid (2.0 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.09 g) and 1-hydroxybenzotriazole monohydrate (0.87 g), and the mixture was further stirred at room temperature for 20 hr. Water was added to the reaction mixture and the precipitated crystals were collected by filtration to give (2E)-3-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-N-methoxy-N-methyl-2-propenamide as colorless crystals (1.92 g, yield 88%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 173-174° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 20 hr
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-11dede9f981d4fd4b3ca0fe56e3781ae
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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