Trifluoroacetic acid → HCID 58318661, compound

HRID 1027927Notes

Reaction equation

HRID 1027927 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]([C@H:11]1[CH2:16][C@H:15]([O:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][C:27]=2[O:28][CH3:29])[N:24]=[CH:23][N:22]=[C:21]3[NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:32]=2[F:38])[CH2:14][CH2:13][N:12]1C(OC(C)(C)C)=O)=[O:10]>C(Cl)Cl>[Cl:37][C:33]1[C:32]([F:38])=[C:31]([NH:30][C:21]2[C:20]3[C:25](=[CH:26][C:27]([O:28][CH3:29])=[C:18]([O:17][C@@H:15]4[CH2:14][CH2:13][NH:12][C@@H:11]([C:9]([NH2:8])=[O:10])[CH2:16]4)[CH:19]=3)[N:24]=[CH:23][N:22]=2)[CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58318672HCID 58318672, compound

Product 1

HCID 58318661HCID 58318661, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 ml) was added over a period of 5 minutes to a stirred solution of tert-butyl (2R,4R)-2-(aminocarbonyl)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)piperidine-1-carboxylate (0.13 g, 0.232 mmol) in DCM (2 ml) at 0° C., was added. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour after which time, the reaction was complete. The reaction mixture was concentrated to dryness, azeotroped twice with toluene and the residue was purified by flash chromatography (silica gel, DCM-NH3/MeOH 5%) to give (2R,4R)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)piperidine-2-carboxamide (9) (0.102 g, 100%) as a yellow solid; Mass Spectrum: (M+H)+ 446.1.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customazeotroped twice with toluene
  4. customthe residue was purified by flash chromatography (silica gel, DCM-NH3/MeOH 5%)

Sources & evidence

ORD record
ord-ac6529183db34f8d94bd5ace3a4ec778
Source dataset
uspto-grants-2014_05
Patent number
US08735410B2

Reaction notes

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