Triethylamine → HCID 21890912, compound

HRID 721587Notes

Reaction equation

HRID 721587 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.C(N(CC)CC)C.ClC(Cl)(O[C:34](=[O:40])OC(Cl)(Cl)Cl)Cl.[CH2:42]([N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(Cl)(Cl)Cl.O>[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:34]([N:52]2[CH2:53][CH2:54][N:49]([CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH2:50][CH2:51]2)=[O:40])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 94429TriphosgeneHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Product 1

HCID 21890912HCID 21890912, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml) to prepare a solution. A solution of triphosgene (151 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 10 min. Next, 1-benzylpiperazine (90 mg) was added thereto, and the mixture was further stirred at room temperature for one hr. Water was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by concentration. The residue was purified on a column using chloroform/methanol to give the title compound (93 mg, yield 55%).

Workup

  1. stirringthe mixture was further stirred at room temperature for one hr
  2. customthe reaction
  3. extractionthe reaction solution was then extracted with chloroform
  4. concentrationfollowed by concentration
  5. customThe residue was purified on a column

Sources & evidence

ORD record
ord-53a75ff757a64e1f8ff9b787edd7c47b
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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