Triphenylphosphine → HCID 22667046, compound

HRID 1375913Notes

Reaction equation

HRID 1375913 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][CH2:26][CH3:27])=[O:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:47]1([CH:53](O)[CH2:54][CH3:55])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]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][CH2:55][CH2:54][CH2:53][N:47]4[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]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][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 3030629HCID 3030629, compound2×HCID 135674211HCID 135674211, compound

Product 1

HCID 22667046HCID 22667046, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{2-Chloro-4-[(7-hydroxy-6-methoxy-4-quinazolinyl)oxy]phenyl}-N′-ethylurea (2.7 g) was dissolved in N,N-dimethylformamide (30 ml), and triphenylphosphine(3.6 g), piperidinopropanol (1.2 g), and diethyl azodicarboxylate (2.4 g) were added to the solution. The mixture was stirred at room temperature for 2 hr. Triphenylphosphine(3.6 g), piperidinopropanol (0.8 g), and diethyl azodicarboxylate (1.9 g) were then again added to the reaction solution. The mixture was stirred at room temperature for additional 10 hr. The solvent was removed by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel by development with chloroform/methanol (20/1) to give 1.5 g (yield 42%) of the title compound.

Workup

  1. stirringThe mixture was stirred 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-9f1a098909ce4b2489b74ffb943935ea
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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