Methanol → HCID 22667184, compound

HRID 1008410Notes

Reaction equation

HRID 1008410 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]([F:23])[CH:17]=1.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[CH2:36]([NH2:40])[CH2:37][CH2:38][CH3:39].CO>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:36]([NH:40][C:28]([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[F:23])=[O:34])[CH2:37][CH2:38][CH3:39]

Participants

7

Reactant 4

HCID 887MethanolHCID 8007ButylamineHCID 94429TriphosgeneHCID 218902744-((6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline

Product 1

HCID 22667184HCID 22667184, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoro-aniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene (47 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, butylamine (24 μl) was added, 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 25 mg (yield 38%) 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-6813071742154d7bb31631119f1b405f
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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