Triphosgene → HCID 21890682, compound

HRID 721495Notes

Reaction equation

HRID 721495 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.[C:38]([C:42]1[CH:54]=[CH:53][C:45]([CH2:46][N:47]2[CH2:51][CH2:50][CH:49]([NH2:52])[CH2:48]2)=[CH:44][CH:43]=1)([CH3:41])([CH3:40])[CH3:39].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)(Cl)Cl>[C:38]([C:42]1[CH:54]=[CH:53][C:45]([CH2:46][N:47]2[CH2:51][CH2:50][CH:49]([NH:52][C:30]([NH:20][C:19]3[CH:21]=[CH:22][C:16]([O:15][C:6]4[C:5]5[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]=[CH:8][N:7]=4)=[CH:17][C:18]=3[N+:23]([O-:25])=[O:24])=[O:36])[CH2:48]2)=[CH:44][CH:43]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

7

Reactant 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 177554014-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroanilineHCID 218908851-[[4-(1,1-Dimethylethyl)phenyl]methyl]-3-pyrrolidinamine

Product 1

HCID 21890682HCID 21890682, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Chloroform (13 ml) and triethylamine (2 ml) were added to 4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline (100 mg) to prepare a solution. Triphosgene (96 mg) was added to the solution, and the mixture was stirred at room temperature for 30 min. 1-[4-(Tert-butyl)benzyl]-3-pyrrolidinamine (102 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 (38 mg, yield 22%).

Workup

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature overnight
  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-bc9ceb22b37a46a2bf455accef326fd5
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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