Tert-butyl 4-(5-bromo-2-(3-chloro-4-morpholinophenylamino) quinazolin-8-yloxy)piperidine-1-carboxylate → 5-bromo-N-(3-chloro-4-morpholinophenyl)-8-(piperidine-4-yloxy) quinazolin-2-amine

HRID 2079676Notes

Reaction equation

HRID 2079676 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[C:8]2[C:3]=1[CH:4]=[N:5][C:6]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:29]([Cl:39])[CH:28]=1)=[N:7]2>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:8]2[C:3]=1[CH:4]=[N:5][C:6]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:29]([Cl:39])[CH:28]=1)=[N:7]2

Participants

3

Reactant 1

HCID 59199220Tert-butyl 4-(5-bromo-2-(3-chloro-4-morpholinophenylamino) quinazolin-8-yloxy)piperidine-1-carboxylate

Product 1

HCID 671022375-bromo-N-(3-chloro-4-morpholinophenyl)-8-(piperidine-4-yloxy) quinazolin-2-amineYield 50%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 4-(5-bromo-2-(3-chloro-4-morpholinophenylamino) quinazolin-8-yloxy)piperidine-1-carboxylate in 30% TFA/DCM was stirred at room temperature for 30 min. The solvent was evaporated and crude was purified by semi-prep HPLC to provide 5-bromo-N-(3-chloro-4-morpholinophenyl)-8-(piperidine-4-yloxy) quinazolin-2-amine in 50% yield. ES/MS m/z 518.0 (MH+).

Workup

  1. customThe solvent was evaporated
  2. customcrude was purified by semi-prep HPLC

Sources & evidence

ORD record
ord-d36497b5cb274c53919dab0e58f925bb
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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