Trifluoroacetic acid → HCID 15547164, compound

HRID 1167167Notes

Reaction equation

HRID 1167167 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]4)=[C:24]([O:27][CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[F:15]>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][NH:39][CH2:40][CH2:41]4)=[C:24]([O:27][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[F:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22995797HCID 22995797, compound

Product 1

HCID 15547164HCID 15547164, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.00 ml trifluoroacetic acid are added dropwise to 740 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-cyclopentyloxy-7-{2-[4-(tert.butyloxycarbonyl)-piperazin-1-yl]-ethoxy}-quinazoline in 10 ml of methylene chloride. The reaction solution is stirred overnight at ambient temperature. For working up the reaction mixture is concentrated by evaporation, combined with 20 ml of water and made alkaline with concentrated aqueous ammonia solution. The aqueous phase is extracted with ethyl acetate. The combined extracts are washed with saturated sodium carbonate solution and saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation. A light yellow solid remains.

Workup

  1. concentrationis concentrated by evaporation
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washThe combined extracts are washed with saturated sodium carbonate solution and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ebed91f8ef574af5ba31c76a97c5b312
Source dataset
uspto-grants-2003_09
Patent number
US06617329B2

Reaction notes

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