Triethylamine → N-[4-(2-Cyclobutanecarbonylaminopyridin-4-yl)oxyphenyl]-N'-(4-fluorophenyl)urea

HRID 1010313Notes

Reaction equation

HRID 1010313 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[NH2:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[O:24])=[CH:18][CH:17]=2)[CH:12]=[CH:11][N:10]=1.C(N(CC)CC)C>O1CCCC1>[CH:1]1([C:5]([NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[O:24])=[CH:18][CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 22936644N-[4-(2-aminopyridin-4-yl)oxyphenyl]-N'-(4-fluorophenyl)urea

Product 1

HCID 22936884N-[4-(2-Cyclobutanecarbonylaminopyridin-4-yl)oxyphenyl]-N'-(4-fluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After adding 70 mg of cyclobutanecarbonyl chloride to a solution of 100 mg of N-[4-(2-aminopyridin-4-yl)oxyphenyl]-N′-(4-fluorophenyl)urea, 0.12 ml of triethylamine and 10 ml of tetrahydrofuran stirred at room temperature, the mixture was further stirred for 15 minutes. 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 (chloroform:methanol=40:1). The obtained residue was solidified from ethyl acetate-methanol-hexane to obtain 64 mg of the target substance as a white solid.

Workup

  1. stirringthe mixture was further stirred for 15 minutes
  2. additionNH type silica gel was added to the reaction solution
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThe silica gel was charged into a dry column
  5. custompacked with NH type silica gel, and column purification
  6. customto obtain 64 mg of the target substance as a white solid

Sources & evidence

ORD record
ord-97d2abe74ea74868ab2fc224e24b552b
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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