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Dimethylformamide → methyl [3-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethoxy]-1-methyl-1H-pyrazol-4-yl]acetate

HRID 1295311
Notes
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Reaction equation

HRID 1295311 reaction equation
[OH:1][C:2]1[C:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:5][N:4]([CH3:12])[N:3]=1.Cl[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)[O:26][C:27]=2[CH3:28])=[N:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:25]1[O:26][C:27]([CH3:28])=[C:23]([CH2:22][O:21][C:18]2[N:19]=[CH:20][C:15]([CH2:14][O:1][C:2]3[C:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:5][N:4]([CH3:12])[N:3]=3)=[CH:16][CH:17]=2)[N:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 230763795-Chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridineHCID 178499559HCID 178499559, compound

Product 1

HCID 86591680methyl [3-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethoxy]-1-methyl-1H-pyrazol-4-yl]acetateYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl (3-hydroxy-1-methyl-1H-pyrazol-4-yl)acetate (298 mg), 5-chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridine (533 mg), potassium carbonate (484 mg) and N,N-dimethylformamide (10 ml) was stirred at 60° C. for 4 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl [3-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethoxy]-1-methyl-1H-pyrazol-4-yl]acetate (623 mg, yield 81%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9ff133b096384d64b3b6c7bb456ed590
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07241785B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes