Hydrochloric Acid → (R)-Pyrrolidin-2-yl((R)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-yl)methanone

HRID 445357

반응식

HRID 445357 반응식
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([OH:15])=O)=O)(C)(C)C.[F:16][C:17]([F:35])([F:34])[C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26][NH:25]2)=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C.O1CCOCC1.O>[NH:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([N:25]1[CH2:26][CH2:27][C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:24]1[C:21]1[CH:22]=[CH:23][C:18]([C:17]([F:16])([F:35])[F:34])=[CH:19][CH:20]=1)=[O:15]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 59536406(R)-Pyrrolidin-2-yl((R)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-yl)methanone

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매2회

실험 절차

To a stirred mixture of (R)-1-(tert-butoxy-carbonyl)pyrrolidine-2-carboxylic acid (0.078 g, 0.36 mmol), (R)-1-(4-(trifluoro-methyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.100 g, 0.36 mmol) and DIEA (0.047 g, 0.36 mmol) in DMF (2 mL) was added HATU (0.14 g, 0.36 mmol). The reaction mixture was continued to stir overnight at RT, hydrolyzed with H2O, extracted with DCM (3×), dried over Na2SO4, concentrated and purified by ISCO (20% EtOAc/hexanes) to give the white solid which was dissolved in p-dioxane (2 mL) and added 1 mL of 4M HCl in p-dioxane. The mixture was continued to stir at RT overnight, concentrated, taken up in H2O, and neutralized by saturated aqueous NaHCO3, and filtered the light yellow solid which was dried by air. MS (ESI, positive ion) m/z: 375 (M+1).

후처리

  1. extractionextracted with DCM (3×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by ISCO (20% EtOAc/hexanes)
  5. customto give the white solid which
  6. concentrationconcentrated
  7. filtrationfiltered the light yellow solid which
  8. customwas dried by air

출처 및 근거

ORD 기록
ord-9a93e900122a4fc9b1bab144aa9bc64f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

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