Triethylamine → HCID 22732299, compound

HRID 1357724Notes

Reaction equation

HRID 1357724 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[CH:9]=[C:10]([CH:26]=[CH:27][C:28]=1[F:29])[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1.C(N(CC)CC)C>C(Cl)Cl>[F:29][C:28]1[CH:27]=[CH:26][C:10]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][C:8]=1[NH:7][C:2]([O:4][CH2:5][CH3:6])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22732322HCID 22732322, compound

Product 1

HCID 22732299HCID 22732299, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl chloroformate (0.058 ml) was added to a suspension of 4-(3-amino-4-fluoroanilino)-6,7-dimethoxyquinazoline (159 mg) and triethylamine (0.14 ml) in dry methylene chloride (3.5 ml) and the resulting mixture was stirred at ambient temperature for 18 hours. Methylene chloride (100 ml) was added and the mixture was washed with water and brine, dried over magnesium sulphate, filtered and evaporated to dryness. The residue was purified by silica column chromatography, eluting with 2% methanol in methylene chloride to yield the title compound as a solid (38 mg, 19%); NMR: 1.23 (t, 3H), 3.91 (s, 3H), 3.94 (s, 3H), 4.12 (m, 2H), 7.16 (s, 1H), 7.21 (m, 1H), 7.57 (m, 1H), 7.83 (s, 1H), 8.0 (m, 1H), 8.42 (s, 1H), 9.28 (s, 1H), 9.49 (s, 1H); m/s: M+H+ 387.

Workup

  1. washthe mixture was washed with water and brine
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica column chromatography
  6. washeluting with 2% methanol in methylene chloride

Sources & evidence

ORD record
ord-a58fa36c4cd347018f7bcfb6c3156939
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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