Hydrochloric Acid → 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]benzoic acid

HRID 2221982Notes

Reaction equation

HRID 2221982 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[C:25]([CH2:27][O:28][C:29]2[C:33](/[CH:34]=[CH:35]/[C:36]3[N:37]=[C:38]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[S:39][C:40]=3[CH3:41])=[CH:32][N:31]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:30]=2)[CH:24]=[CH:23][C:4]=1[O:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18]C)=[O:17])[O:10][C:11]=1[CH3:12].O1CCCC1.[OH-].[Na+].Cl>O.CO>[CH3:1][O:2][C:3]1[CH:26]=[C:25]([CH2:27][O:28][C:29]2[C:33](/[CH:34]=[CH:35]/[C:36]3[N:37]=[C:38]([N:42]4[CH2:43][CH2:44][O:45][CH2:46][CH2:47]4)[S:39][C:40]=3[CH3:41])=[CH:32][N:31]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[N:30]=2)[CH:24]=[CH:23][C:4]=1[O:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([OH:18])=[O:17])[O:10][C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69217039methyl 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

Product 1

HCID 692151943-[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]benzoic acidYield 72.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 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 (0.35 g), tetrahydrofuran (50 mL) and methanol (20 mL) was added 1N aqueous sodium hydroxide solution (20 mL), and the mixture was heated under reflux for 2 hrs. 1N Hydrochloric acid and water were added to acidify the reaction mixture, and the precipitated crystals were collected by filtration and washed with diethyl ether to give 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]benzoic acid as brown crystals (0.25 g, yield 71%). Recrystallization from acetone-hexane gave brown prism crystals. melting point: 215-217 (dec) ° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a8e9be2f357b4ee1ae314e3f7ca5e7c5
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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