Triethylamine → N-{4-[2-(Butyroylamino)pyridin-4-yl]oxyphenyl}-N'-cyclopropylurea

HRID 387929Notes

Reaction equation

HRID 387929 reaction equation
[C:1]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])OC3C=CC=CC=3)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH:30]1([NH2:33])[CH2:32][CH2:31]1.C(N(CC)CC)C>O1CCCC1>[C:1]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([NH:33][CH:30]3[CH2:32][CH2:31]3)=[O:29])=[CH:18][CH:19]=2)[CH:10]=[CH:9][N:8]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 58931168Phenyl N-(4-[2-(butyroylamino)pyridin-4-yl]oxyphenyl)carbamate

Product 1

HCID 58931404N-{4-[2-(Butyroylamino)pyridin-4-yl]oxyphenyl}-N'-cyclopropylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl N-{4-[2-(butyroylamino)pyridin-4-yl]oxyphenyl}carbamate (0.116 g), cyclopropylamine (0.034 g), triethylamine (0.041 ml) and tetrahydrofuran (10 ml) were heated together in a sealed tube at 100° C. for 1 hour. NH type silica gel was added to the reaction solution, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (ethyl acetate). The solvent was distilled off under reduced pressure, ethyl acetate and hexane were added to the residue, and the precipitated solid was filtered out to obtain 20 mg of the target substance as a white solid.

Workup

  1. additionNH type silica gel was added to the reaction solution
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe silica gel was charged into a dry column
  4. custompacked with NH type silica gel, and column purification
  5. distillationThe solvent was distilled off under reduced pressure, ethyl acetate and hexane
  6. additionwere added to the residue
  7. filtrationthe precipitated solid was filtered out
  8. customto obtain 20 mg of the target substance as a white solid

Sources & evidence

ORD record
ord-4c5bdbf2775c45589281a0b7fb04241a
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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