HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dimethylformamide → diethyl (E)-2-(3-{[4-({2-[3-(carbamoyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)-3-methoxybenzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate

HRID 2221928
Notes
Print preview

Reaction equation

HRID 2221928 reaction equation
[CH2:1]([O:3][P:4](/[CH:9]=[CH:10]/[C:11]1[C:12]([O:22][CH2:23][C:24]2[CH:46]=[CH:45][C:27]([O:28][CH2:29][C:30]3[N:31]=[C:32]([C:36]4[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=4)[C:39](O)=[O:40])[O:33][C:34]=3[CH3:35])=[C:26](OC)[CH:25]=2)=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].Cl.C([N:52]=C=NCCCN(C)C)C.CN(C)[CH:63]=[O:64]>O>[C:39]([C:38]1[CH:37]=[C:36]([C:32]2[O:33][C:34]([CH3:35])=[C:30]([CH2:29][O:28][C:27]3[CH:45]=[CH:46][C:24]([CH2:23][O:22][C:12]4[C:11](/[CH:10]=[CH:9]/[P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8])=[CH:15][N:14]([C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=5)[N:13]=4)=[CH:25][C:26]=3[O:64][CH3:63])[N:31]=2)[CH:44]=[CH:43][CH:42]=1)(=[O:40])[NH2:52]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 100552733-[4-({4-[({4-[(E)-2-(diethoxyphosphoryl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]benzoic acid

Product 1

HCID 86605871diethyl (E)-2-(3-{[4-({2-[3-(carbamoyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)-3-methoxybenzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate
Yield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[4-({4-[({4-[(E)-2-(diethoxyphosphoryl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]benzoic acid (1.09 g), 1-hydroxybenzotriazole ammonia complex (0.37 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.46 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 to give diethyl (E)-2-(3-{[4-({2-[3-(carbamoyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)-3-methoxybenzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate as colorless crystals (0.82 g, yield 76%). Recrystallization from acetone-hexane gave colorless prism crystals. melting point: 127-128° 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

Sources & evidence

ORD record
ord-9ee511409ed4458d95619bd5d79fdbb0
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368578B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes