Triphosgene → HCID 58738945, compound

HRID 721491Notes

Reaction equation

HRID 721491 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])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[CH2:38]([N:45]1[CH2:49][CH2:48][C@H:47]([NH2:50])[CH2:46]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)(Cl)Cl>[CH2:38]([N:45]1[CH2:49][CH2:48][C@H:47]([NH:50][C:30]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)=[CH:17][C:18]=2[N+:23]([O-:25])=[O:24])=[O:36])[CH2:46]1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 177554014-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline

Product 1

HCID 58738945HCID 58738945, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Chloroform (27 ml) and triethylamine (4 ml) were added to 4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline (200 mg) to prepare a solution. Triphosgene (192 mg) was added to the solution, and the mixture was stirred at room temperature for 30 min. (3S)-(+)-1-Benzyl-3-aminopyrrolidine (77 mg) was then added thereto, and the mixture was stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The extract was washed with saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/acetone for development. Diethyl ether was added to the purification product, and the precipitated crystal was collected by filtration and was washed to give the title compound (153 mg, yield 48%).

Workup

  1. customto prepare a solution
  2. additionwas then added
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by thin-layer chromatography
  8. additionDiethyl ether was added to the purification product
  9. filtrationthe precipitated crystal was collected by filtration
  10. washwas washed

Sources & evidence

ORD record
ord-0a5af0b8be124b0fa525a7f4a98d571a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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