Trifluoroacetic acid → 2-(2-(2-(2-((2-Ethyl-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide

HRID 705766노트

반응식

HRID 705766 반응식
[NH2:1][C:2](=[O:44])[CH2:3][C:4]1[CH:43]=[CH:42][CH:41]=[CH:40][C:5]=1[CH2:6][CH2:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)=[CH:21][C:20]=2[CH2:38][CH3:39])[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:38]([C:20]1[CH:21]=[C:22]([CH:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]2)[CH:23]=[CH:24][C:19]=1[NH:18][C:10]1[N:9]=[C:8]([CH2:7][CH2:6][C:5]2[CH:40]=[CH:41][CH:42]=[CH:43][C:4]=2[CH2:3][C:2]([NH2:1])=[O:44])[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=1)[CH3:39]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 71232246tert-Butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-ethylphenyl)piperidine-1-carboxylate

생성물 1

HCID 601622462-(2-(2-(2-((2-Ethyl-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-ethylphenyl)piperidine-1-carboxylate, (I44) (120 mg, 0.20 mmol) was dissolved in DCM (20 mL), TFA (2 mL) was added and the mixture stirred for 16 hours at room temperature. The mixture was concentrated and the residue suspended in 10% sodium hydroxide (10 mL) and brine (10 mL). The mixture was extracted with ethyl acetate (4×20 mL), the combined extracts washed with brine, dried (sodium sulphate) evaporated and the residue evaporated for ether to give the title compound (8) (93 mg, 93% yield) as a white solid; 1H NMR (400 MHz, d6-DMSO) δ 9.47 (s, 1H), 8.49 (s, 1H), 7.37 (s, 1H), 7.26-7.18 (m, 2H), 7.17-7.09 (m, 4H), 7.05 (dd, J=8.2, 1.9 Hz, 1H), 6.89 (s, 1H), 3.44 (s, 2H), 3.09-2.88 (m, 6H), 2.62-2.54 (m, overlaps with DMSO), 1.70 (d, J=11.4 Hz, 2H), 1.52 (qd, J=12.3, 3.7 Hz, 2H), 1.10 (t, J=7.5 Hz, 3H), LCMS Method C: 4.96 min; m/z 512.2 [M+H]+, 534.2 [M+Na]+; m/z 510.2 [M−H]−.

후처리

  1. concentrationThe mixture was concentrated
  2. extractionThe mixture was extracted with ethyl acetate (4×20 mL)
  3. washthe combined extracts washed with brine
  4. dry with materialdried (sodium sulphate)
  5. customevaporated
  6. customthe residue evaporated for ether

출처 및 근거

ORD 기록
ord-4c5e3e7e28294fd1909ea3fdce08b494
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174946B2

반응 노트

불러오는 중…