(3R)-tert-Butyl 3-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)piperidine-1-carboxylate → N-((R)-Piperidin-3-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445270

반응식

HRID 445270 반응식
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:19]([NH:21][C@@H:22]2[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]2)=[O:20])=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O>[NH:24]1[CH2:25][CH2:26][CH2:27][C@@H:22]([NH:21][C:19]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:35])[F:36])=[CH:8][CH:7]=2)=[O:20])[CH2:23]1

참가 물질

3

반응물 1

HCID 59536392(3R)-tert-Butyl 3-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)piperidine-1-carboxylate

생성물 1

HCID 59536393N-((R)-Piperidin-3-yl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of (3R)-tert-butyl 3-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-isoquinoline-2-carboxamido)piperidine-1-carboxylate (44 mg, 87 μmol, example 20) in TFA (30% in DCM, 2 mL) was stirred at RT for 30 min. The solvents were removed and EtOAc (5 mL) and saturated NaHCO3 (3 mL) were added to the residue. The solution mixture was then stirred at RT for 10 min. The organic layer was collected and the aqueous layer was extracted with EtOAc (2×2 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried under vacuum to give the title compound as an off-white solid. MS (ESI, positive ion) m/z: 404 (M+H).

후처리

  1. customThe solvents were removed
  2. additionEtOAc (5 mL) and saturated NaHCO3 (3 mL) were added to the residue
  3. customThe organic layer was collected
  4. extractionthe aqueous layer was extracted with EtOAc (2×2 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-96671b9701f2407193dd2a1ed1ac3754
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

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