Triethylamine → HCID 22387686, compound

HRID 1072730Notes

Reaction equation

HRID 1072730 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:21]([OH:23])=O)=[C:9]2[CH3:24])=[CH:4][CH:3]=1.[CH2:27]([NH2:37])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[CH:11][C:10]([C:21]([NH:37][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])=[C:9]2[CH3:24])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 8916Decylamine2×HCID 76257Diethyl cyanophosphonate2×HCID 22387451HCID 22387451, compound

Product 1

HCID 22387686HCID 22387686, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-bromophenethyl)-5-(4-methoxyphenyl)-2-methyl-1H-pyrrole-3-carboxylic acid (2.00 g, 4.83 mmol) in DMF (10 ml) were added n-decylamine (838 mg, 5.33 mmol), diethyl cyanophosphate (946 mg, 5.80 mmol) and triethylamine (0.673 ml, 4.83 mmol), and the mixture was stirred for 1 hour at room temperature. To the reaction solution were added n-decylamine (838 mg, 5.33 mmol), diethyl cyanophosphate (946 mg, 5.80 mmol) and triethylamine (0.673 ml, 4.83 mmol) and the mixture was stirred room temperature for 2 hours. The mixture was poured into water and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid, water and saturated aqueous sodium bicarbonate and dried over magnesium sulfate anhydride, and solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the object compound as a solid. 2.16 g (80.9%)

Workup

  1. stirringthe mixture was stirred room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with 1N hydrochloric acid, water and saturated aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate anhydride, and solvent
  5. customwas removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-715c0fd45a9e45beb0b27ed1eff5f9d3
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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