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Trifluoroacetic acid → 2-(2-(2-(2-((6-(Piperidin-4-yl)pyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592477
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HRID 592477 반응식
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:50])[CH:10]([C:12]1[CH:49]=[CH:48][CH:47]=[CH:46][C:13]=1[CH2:14][CH2:15][C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][N:19]=[C:18]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([CH:33]3[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]3)=[N:31][CH:32]=2)[N:17]=1)[CH3:11]>C(Cl)Cl>[NH:36]1[CH2:37][CH2:38][CH:33]([C:30]2[N:31]=[CH:32][C:27]([NH:26][C:18]3[N:17]=[C:16]([CH2:15][CH2:14][C:13]4[CH:46]=[CH:47][CH:48]=[CH:49][C:12]=4[CH:10]([CH3:11])[C:9]([NH2:8])=[O:50])[C:21]([C:22]([F:24])([F:23])[F:25])=[CH:20][N:19]=3)=[CH:28][CH:29]=2)[CH2:34][CH2:35]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86712343tert-Butyl 4-(5-((4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate

생성물 1

HCID 732952962-(2-(2-(2-((6-(Piperidin-4-yl)pyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide수율 134%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (0.50 mL, 6.5 mmol) was added to tert-butyl 4-(5-((4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate A72 (0.060 g, 0.099 mmol) in DCM (5 mL) and the mixture was stirred for 2 hours. The mixture was concentrated under reduced pressure and quenched with 25% aq. NaOH (20 mL). The aqueous phase was extracted with EtOAc (3×20 mL) before the combined organics were dried (phase separation cartridge) and concentrated under reduced pressure. The suspension was sonicated with hexane and concentrated under reduced pressure to give the title compound (0.066 g, 134% residual solvent/water). LCMS-D: rt 3.025 min; m/z 499.3 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customquenched with 25% aq. NaOH (20 mL)
  3. extractionThe aqueous phase was extracted with EtOAc (3×20 mL) before the combined
  4. customorganics were dried
  5. custom(phase separation cartridge)
  6. concentrationconcentrated under reduced pressure
  7. customThe suspension was sonicated with hexane
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-975140aeb688436383aae2a33f486009
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238644B2

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