Methanol → HCID 22667130, compound

HRID 1375819Notes

Reaction equation

HRID 1375819 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.[CH2:35]([NH2:38])[CH2:36][CH3:37].CO>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:27]([NH:38][CH2:35][CH2:36][CH3:37])=[O:33])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7852PropylamineHCID 94429TriphosgeneHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Product 1

HCID 22667130HCID 22667130, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.2 ml), and a solution of triphosgene (50 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, propylamine (21 μl) was added to the reaction solution, and the mixture was further stirred at room temperature overnight. Methanol was added to the reaction solution, and the solution was purified by HPLC by development with chloroform/methanol to give 30 mg (yield 47%) of the title compound.

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. customthe solution was purified by HPLC by development with chloroform/methanol

Sources & evidence

ORD record
ord-305c70b132d844e6bea4b619f2bb747e
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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