Triethylamine → HCID 18753485, compound

HRID 2227944Notes

Reaction equation

HRID 2227944 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].FC(F)(F)C(O)=O.[NH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[F:39])=[N:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:40][CH3:41].C(N(CC)CC)C>C1COCC1>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([NH:31][C:25]2[C:24]3[C:29](=[CH:30][C:21]([O:20][CH2:19][CH2:18][CH2:17][NH:16][C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3])=[C:22]([O:40][CH3:41])[CH:23]=3)[N:28]=[CH:27][N:26]=2)=[C:33]([F:39])[CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 22478258HCID 22478258, compound

Product 1

HCID 18753485HCID 18753485, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate (88 mg, 5.9 mmol) was added to a stirred solution of 7-(3-aminopropoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline trifluoroacetate (151 mg, 0.4 mmol) and triethylamine (0.2 ml, 1.4 mmol) in THF (15 ml). The reaction mixture was stirred at ambient temperature for 30 minutes and the volatiles were removed by evaporation. The residue was dissolved in methylene chloride, the solution was washed with aqueous sodium hydrogen carbonate solution and then brine, dried (MgSO4) and the solvent was removed by evaporation. The residue was recrystallised from acetonitrile to give 4-(4-chloro-2-fluoroanilino)-7-(3-[N-isobutoxycarbonylamino]propoxy)-6-methoxyquinazoline (41.2 mg, 20%) as a white solid.

Workup

  1. customthe volatiles were removed by evaporation
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washthe solution was washed with aqueous sodium hydrogen carbonate solution
  4. dry with materialbrine, dried (MgSO4)
  5. customthe solvent was removed by evaporation
  6. customThe residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-357759567040488b9d3b5cbaa303d8a3
Source dataset
uspto-grants-2002_07
Patent number
US06414148B1

Reaction notes

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