Triphenylphosphine Oxide → 7-[2-(4-acetylpiperazin-1-yl)ethoxy]-4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazoline

HRID 916447Notes

Reaction equation

HRID 916447 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[C:17]([F:26])=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20]([CH3:25])=[CH:19]4)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:27][CH3:28].C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49]([N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)(=[O:51])[CH3:50]>CN(C)C=O>[C:49]([N:52]1[CH2:57][CH2:56][N:55]([CH2:2][CH2:3][O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([O:15][C:16]4[C:17]([F:26])=[C:18]5[C:22](=[CH:23][CH:24]=4)[NH:21][C:20]([CH3:25])=[CH:19]5)=[N:10][CH:11]=[N:12]3)=[CH:7][C:6]=2[O:27][CH3:28])[CH2:54][CH2:53]1)(=[O:51])[CH3:50]

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 837951-AcetylpiperazineHCID 58960237HCID 58960237, compound

Product 1

HCID 117522547-[2-(4-acetylpiperazin-1-yl)ethoxy]-4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolineYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(2-bromoethoxy)-4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazoline (310 mg of a sample containing triphenylphosphine oxide (approx. 12% w/w), 0.61 mmol) and 1-acetylpiperazine (258 mg, 2.02 mmol) in N,N-dimethylformamide (5 ml) was stirred at ambient temperature overnight and then concentrated under reduced pressure. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 7-[2-(4-acetylpiperazin-1-yl)ethoxy]-4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazoline (202 mg, 67%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography
  3. washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-292ffc0bcc554e04bebf9ce1e46e19a0
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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