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

HRID 1192367노트

반응식

HRID 1192367 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.)

후처리

  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

출처 및 근거

ORD 기록
ord-f20503305f314116887bd4ec546fd29a
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680114B2

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