Tetrahydrofuran → HCID 58930913, compound

HRID 1010190Notes

Reaction equation

HRID 1010190 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH2:7][C:8]1[C:13]([C:14]#[CH:15])=[C:12]([O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[O:25])=[CH:19][CH:18]=2)[CH:11]=[CH:10][N:9]=1.C(N(CC)CC)C.[O:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1>>[CH:1]1([C:4]([N:7]([C:8]2[C:13]([C:14]#[CH:15])=[C:12]([O:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24]([NH:26][C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)=[O:25])=[CH:21][CH:22]=3)[CH:11]=[CH:10][N:9]=2)[C:45]([CH:44]2[CH2:42][CH2:43]2)=[O:41])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 58931407HCID 58931407, compound

Product 1

HCID 58930913HCID 58930913, compound

Procedure

After adding 57 mg of cyclopropanecarbonyl chloride to a solution of N-(4-{[2-amino-3-(1-ethynyl)-4-pyridyl]oxy}phenyl)-N′-(4-fluorophenyl)urea (100 mg), triethylamine (0.12 ml) and tetrahydrofuran (5 ml) while stirring at room temperature, stirring was continued for 1.5 hours. After adding NH type silica gel 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 organic solvent was distilled off under reduced pressure, and methanol and water were added to the residue for solidification to obtain 15 mg of the target substance as a white powder.

Workup

  1. stirringstirring
  2. additionAfter adding NH type silica gel 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. distillationThe organic solvent was distilled off under reduced pressure, and methanol and water
  7. additionwere added to the residue for solidification
  8. customto obtain 15 mg of the target substance as a white powder

Sources & evidence

ORD record
ord-f8d87f691d73495a86e6818c2bddc84d
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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