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

HRID 1779008노트

반응식

HRID 1779008 반응식
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:49])[CH2:10][C:11]1[CH:48]=[CH:47][CH:46]=[CH:45][C:12]=1[CH2:13][CH2:14][C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][N:18]=[C:17]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([CH:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)=[N:30][CH:31]=2)[N:16]=1>C(Cl)Cl>[NH:35]1[CH2:36][CH2:37][CH:32]([C:29]2[N:30]=[CH:31][C:26]([NH:25][C:17]3[N:16]=[C:15]([CH2:14][CH2:13][C:12]4[CH:45]=[CH:46][CH:47]=[CH:48][C:11]=4[CH2:10][C:9]([NH2:8])=[O:49])[C:20]([C:21]([F:23])([F:22])[F:24])=[CH:19][N:18]=3)=[CH:27][CH:28]=2)[CH2:33][CH2:34]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86712663tert-Butyl 4-(5-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate

생성물 1

HCID 730543142-(2-(2-(2-((6-(Piperidin-4-yl)pyridin-3-yl)-amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide수율 85.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (0.5 mL) was added to a solution of tert-butyl 4-(5-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate (A47) (58 mg, 0.099 mmol) in DCM (5 mL) and the resulting solution stirred for 18 hours at room temperature. The volatiles were evaporated under reduced pressure and the residue partitioned between 2 M aqueous NaOH (10 mL) and EtOAc (25 mL). The organic layer was separated and washed with water (25 mL), brine (25 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound 13 as a white solid (41 mg, 85%); 1H NMR (400 MHz, d4-MeOH) δ 8.78 (d, J=2.1 Hz, 1H), 8.61 (d, J=0.6 Hz, 1H), 8.19 (dd, J=8.6, 2.6 Hz, 1H), 7.31 (d, J=8.5 Hz, 1H), 7.26 (d, J=6.3 Hz, 1H), 7.24-7.15 (m, 3H), 3.67 (s, 2H), 3.22-3.15 (m, 4H), 3.14-3.05 (m, 2H), 2.90-2.70 (m, 3H), 1.93 (d, J=13.9 Hz, 2H), 1.75 (m, 2H). LCMS-A: rt 4.552 min; m/z 485 [M+H]+.

후처리

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe residue partitioned between 2 M aqueous NaOH (10 mL) and EtOAc (25 mL)
  3. customThe organic layer was separated
  4. washwashed with water (25 mL), brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cb78e7e82d1b4bd193b8d7e46c7473f8
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266864B2

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