Diisopropylcarbodiimide → (R)-(1-Methyl-4H-pyrazol-3-yl)(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone

HRID 445302

반응식

HRID 445302 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[CH3:21][N:22]1[CH:26]=[CH:25][C:24]([C:27](O)=[O:28])=[N:23]1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C>CN(C=O)C.CO>[CH3:21][N:22]1[CH2:26][CH2:25][C:24]([C:27]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=2)=[O:28])=[N:23]1

참가 물질

7

반응물 4

HCID 12734DiisopropylcarbodiimideHCID 5731761-methyl-1H-pyrazole-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 68499689(R)-(1-Methyl-4H-pyrazol-3-yl)(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (58 mg, 0.21 mmol, example 30, step 1) in DMF (1 mL) was added 1-methyl-1H-pyrazole-3-carboxylic acid (Fluorochem, 34 mg, 0.27 mmol), 1-hydroxybenzo-triazole hydrate (42 mg, 0.27 mmol), and N-((isopropylimino)methylene)propan-2-amine (66 μL, 0.42 mmol). The resulting mixture was then stirred at RT for 16 h. Then, the mixture was filtered and the filtrate was purified by preparative HPLC to give the target compound. The product was dissolved in MeOH and passed through PL-HCO3 MP resin and the resin was washed with MeOH (2×0.3 mL). The combined filtrates were concentrated and dried under vacuum to give the title compound as a light-yellow solid. MS (ESI, positive ion) m/z: 386 (M+H).

후처리

  1. filtrationThen, the mixture was filtered
  2. customthe filtrate was purified by preparative HPLC
  3. customto give the target compound
  4. washthe resin was washed with MeOH (2×0.3 mL)
  5. concentrationThe combined filtrates were concentrated
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-f558038625ab4c0e95c776ae20159a66
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

연결된 노트

불러오는 중…