Triethylamine → HCID 86759737, compound

HRID 2182553Notes

Reaction equation

HRID 2182553 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].F[C:10](F)(F)[C:11]([OH:13])=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][N:22]=[CH:21]2.[CH2:28]([N:30](CC)CC)C>C1COCC1>[CH2:5]([O:4][C:2]([NH:30][CH2:28][CH2:10][CH2:11][O:13][C:23]1[N:22]=[CH:21][C:20]2[C:25](=[CH:26][CH:27]=[C:18]([O:17][CH3:16])[CH:19]=2)[N:24]=1)=[O:3])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 86759738HCID 86759738, compound

Product 1

HCID 86759737HCID 86759737, compoundYield 30.9%

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-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 (41.2mg, 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-c17b4abad68e44d2bf909aa5ec6517f4
Source dataset
uspto-grants-2005_05
Patent number
US06897210B2

Reaction notes

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