Ethyl chloroformate → HCID 3054083, compound

HRID 1449162Notes

Reaction equation

HRID 1449162 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:2]1.C(Cl)(=O)OCC.[CH3:17][O:18][C:19]1[CH:24]=[C:23]2[C:25]([NH2:35])=[N:26][C:27]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[N:28][C:22]2=[CH:21][C:20]=1[O:36][CH3:37]>C(N(CC)CC)C.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=[CH:7][C:8]([N:32]2[CH2:33][CH2:34][N:29]([C:27]3[N:26]=[C:25]([NH2:35])[C:23]4[C:22](=[CH:21][C:20]([O:36][CH3:37])=[C:19]([O:18][CH3:17])[CH:24]=4)[N:28]=3)[CH2:30][CH2:31]2)=[O:10])=[CH:2]1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazolineHCID 7363153-Furanacrylic acid

Product 1

HCID 3054083HCID 3054083, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 276 mg. (2 mM) of 3-(furan-3-yl)acrylic acid, and 242 mg. (2.4 mM) of triethylamine in 10 ml. of ethyl acetate was added dropwise under ice-cooling a solution of 260 mg. (2.4 mM) of ethyl chlorocarbonate in 5 ml. of ethyl acetate. The resulting mixture was stirred for 3 hours and 761 mg. (2 mM) of 2-piperazine-4-amino-6,7-dimethoxyquinazoline and 484 mg. (4.8 mM) of triethylamine were odded thereto. Stirring was continued at room temperature for further one day. The precipitate thus separated was recovered by filtration and washed well with water to give 480 mg. of the desired product.

Workup

  1. additionTo a mixture of 276 mg
  2. temperaturecooling a solution of 260 mg
  3. stirringStirring
  4. waitwas continued at room temperature for further one day
  5. customThe precipitate thus separated
  6. filtrationwas recovered by filtration
  7. washwashed well with water
  8. customto give 480 mg

Sources & evidence

ORD record
ord-57091ae41af34d889226c56863e109ea
Source dataset
uspto-grants-1980_02
Patent number
US04189484

Reaction notes

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