Trifluoroacetic acid → 2-Amino-3-(4-chloro-2-methyl-phenyl)-1-(4-quinazolin-4-yl-piperazin-1-yl)-propan-1-one dihydrochloride

HRID 1192367Notes

Reaction equation

HRID 1192367 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[CH3:35])[C:9](=[O:26])[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH2:12][CH2:11]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[ClH:34].[ClH:34].[NH2:7][CH:8]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[CH3:35])[C:9]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH2:12][CH2:11]1)=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67539682[1-(4-Chloro-2-methylbenzyl)-2-oxo-2-(4-quinazolin-4-yl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 675394222-Amino-3-(4-chloro-2-methyl-phenyl)-1-(4-quinazolin-4-yl-piperazin-1-yl)-propan-1-one dihydrochlorideYield 228.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing [1-(4-Chloro-2-methylbenzyl)-2-oxo-2-(4-quinazolin-4-yl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester (0.30 g, 0.59 mmol) in 30 mL of DCM under a nitrogen atmosphere was added TFA (1.4 mL.) After stirring at room temperature overnight, the reaction was concentrated under reduced pressure. The residue was dissolved in DCM and 2N HCl in ether added. The solids were filtered and dried to afford 2-Amino-3-(4-chloro-2-methyl-phenyl)-1-(4-quinazolin-4-yl-piperazin-1-yl)-propan-1-one dihydrochloride (0.217 g) as an off-white solid. LCMS (APCI+) m/z 410 [M+H]+; Rt: 1.87 min. 1H NMR (D2O, 400 MHz) δ 8.48 (1H, s), 7.91-7.86 (2H, m), 7.66-7.59 (2H, m), 7.08-7.02 (2H, m), 4.60-4.54 (1H,m), 4.20-4.12 (1H, m), 3.86-3.72 (3H, m), 3.61-3.38 (2H, m), 3.28-3.16 (2H, m), 3.01-2.94 (1H, m), 2.76-2.68 (1H, m), 2.19 (3H, s.)

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DCM
  3. addition2N HCl in ether added
  4. filtrationThe solids were filtered
  5. customdried

Sources & evidence

ORD record
ord-f20503305f314116887bd4ec546fd29a
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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