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Dimethylformamide → methyl 3-[4-({2-methoxy-4-[({4-[(E)-2-(5-methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]phenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]benzoate

HRID 2221981
Notes
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Reaction equation

HRID 2221981 reaction equation
[CH:1]([C:3]1[C:4]([O:14][CH2:15][C:16]2[CH:39]=[CH:38][C:19]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=4)[C:31]([O:33][CH3:34])=[O:32])[O:25][C:26]=3[CH3:27])=[C:18]([O:40][CH3:41])[CH:17]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)=O.[Cl-].[CH3:43][C:44]1[S:48][C:47]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)=[N:46][C:45]=1[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:74](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:41][O:40][C:18]1[CH:17]=[C:16]([CH2:15][O:14][C:4]2[C:3](/[CH:1]=[CH:74]/[C:45]3[N:46]=[C:47]([N:49]4[CH2:50][CH2:51][O:52][CH2:53][CH2:54]4)[S:48][C:44]=3[CH3:43])=[CH:7][N:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]=2)[CH:39]=[CH:38][C:19]=1[O:20][CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=2)[C:31]([O:33][CH3:34])=[O:32])[O:25][C:26]=1[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23076597(5-Methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)triphenylphosphonium chlorideHCID 86605898methyl 3-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate

Product 1

HCID 69217039
methyl 3-[4-({2-methoxy-4-[({4-[(E)-2-(5-methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]phenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]benzoate
Yield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate (1.05 g), (5-methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)triphenylphosphonium chloride (1.40 g), potassium carbonate (0.39 g) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:3, v/v) to give methyl 3-[4-({2-methoxy-4-[({4-[(E)-2-(5-methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]phenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]benzoate as pale-yellow crystals (0.55 g, yield 40%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 183-184° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-85cfc63f784140e3b77d905b3cb5b1e0
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368578B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes