Dimethylformamide → HCID 86605840, compound

HRID 2221896Notes

Reaction equation

HRID 2221896 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:44]=[CH:43][C:39]([C:40]([OH:42])=O)=[CH:38][CH:37]=4)[O:33][C:34]=3[CH3:35])=[C:26]([O:47][CH3:48])[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)C=O>O>[C:40]([C:39]1[CH:38]=[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:47][CH3:48])[N:31]=2)=[CH:44][CH:43]=1)(=[O:42])[NH2:52]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86605838HCID 86605838, compound

Product 1

HCID 86605840HCID 86605840, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[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 (0.18 g), 1-hydroxybenzotriazole ammonia complex (0.06 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.08 g) and N,N-dimethylformamide (5 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-[4-(carbamoyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)-3-methoxybenzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate as colorless crystals (0.15 g, yield 83%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 146-148° 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-2c96402b6ba04352a28457644885ee8c
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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