Triphenylphosphine → HCID 22667157, compound

HRID 1008479Notes

Reaction equation

HRID 1008479 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:21])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:22][C:23]([NH:25][CH3:26])=[O:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:46]1([CH:52](O)[CH2:53][CH3:54])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1.N(C(OCC)=O)=NC(OCC)=O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:54][CH2:53][CH2:52][N:46]4[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:22][C:23]([NH:25][CH3:26])=[O:24]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 3030629HCID 3030629, compound2×HCID 135674221HCID 135674221, compound

Product 1

HCID 22667157HCID 22667157, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{2-Chloro-4-[(7-hydroxy-6-methoxy-4-quinaz-olinyl)oxy]phenyl}-N′-methylurea (2.0 g) was dissolved in N,N-dimethylformamide (50 ml), and triphenylphosphine (2.8 g), piperidinopropanol (0.9 g), and diethyl azodicarboxylate (1.9 g) were added to the solution. The mixture was stirred at room temperature for 2 hr. Triphenylphosphine (2.8 g), piperidinopropanol (0.6 g), and diethyl azodicarboxylate (1.9 g) were then again added to the reaction solution, followed by stirring at room temperature for additional 10 hr. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/methanol (20/1) to give 650 mg (yield 25%) of the title compound.

Workup

  1. stirringby stirring at room temperature for additional 10 hr
  2. customThe solvent was removed by distillation under the reduced pressure
  3. customThe residue was purified by chromatography on silica gel by development with chloroform/methanol (20/1)

Sources & evidence

ORD record
ord-b2e193495e234f0ebcd362dcff3bbecb
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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