Toluene → HCID 22624969, compound

HRID 279589Notes

Reaction equation

HRID 279589 reaction equation
C(O)(C(F)(F)F)=[O:2].[Cl:8][C:9]1[CH:39]=[CH:38][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][N:29](C)[C:30](OC(C)(C)C)=O)=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:40])[CH:10]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[OH2:2].[ClH:8].[Cl:8][C:9]1[CH:39]=[CH:38][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][NH:29][CH3:30])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:40])[CH:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 226250154-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(N-methyl-N-t-butoxycarbonylamino)ethoxy)quinazoline

Product 1

HCID 22624969HCID 22624969, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (4 ml) was added to a solution of 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(N-methyl-N-t-butoxycarbonylamino)ethoxy)quinazoline (390 mg, 0.82 mmol) in methylene chloride (4 ml) and the mixture stirred for 2 hours at ambient temperature. Toluene was added and the volatiles were removed by evaporation. The residue was dissolved in methylene chloride and 3M ethereal hydrogen chloride (1 ml) was added. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(methylamino)ethoxy)quinazoline hydrochloride hydrate (290 mg; 79%).

Workup

  1. customthe volatiles were removed by evaporation
  2. dissolutionThe residue was dissolved in methylene chloride
  3. addition3M ethereal hydrogen chloride (1 ml) was added
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-9bba5cac434c4598925428fb6e397dd4
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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