Methanol → HCID 22667191, compound

HRID 1375861Notes

Reaction equation

HRID 1375861 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])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[CH2:38]([NH2:42])[CH2:39][CH2:40][CH3:41].CO>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:38]([NH:42][C:30]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)=[CH:17][C:18]=1[N+:23]([O-:25])=[O:24])=[O:36])[CH2:39][CH2:40][CH3:41]

Participants

7

Reactant 4

HCID 887MethanolHCID 8007ButylamineHCID 94429TriphosgeneHCID 177554014-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline

Product 1

HCID 22667191HCID 22667191, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline (50 mg) was dissolved in chloroform (10 ml) and triethylamine (0.2 ml), and a solution of triphosgene (43 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, butylamine (22 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 mixture was purified by HPLC by development with chloroform/methanol to give 15 mg (yield 23%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-29f245f7f7164b6097ece2cc55036484
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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