Acetic Acid → HCID 118417117, 화합물

HRID 1483046노트

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HRID 1483046 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:12][CH2:13][NH:14][C:15](=O)OC(C)(C)C.FC(F)(F)C(O)=O.[F:29][C:30]([F:46])([F:45])[C@@H:31]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[C:32]1[CH:37]=[CH:36][C:35](C=O)=[CH:34][CH:33]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:65]>C(Cl)Cl.CO>[ClH:65].[F:46][C:30]([F:29])([F:45])[C@@H:31]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[C:32]1[CH:33]=[CH:34][C:35]([CH2:15][NH:14][CH2:13][CH2:12][N:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]2=[O:1])=[CH:36][CH:37]=1

참가 물질

9

반응물 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 86691246HCID 86691246, 화합물HCID 90135616HCID 90135616, 화합물

생성물 1

HCID 118417117HCID 118417117, 화합물수율 4.1%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6344Dichloromethane용매

실험 절차

Dissolve tert-butyl 2-(1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)ethylcarbamate (220 mg, 0.76 mmol) in DCM (3 mL) and add trifluoroacetic acid (1 mL, 13.23 mmol). Stir at ambient temperature for 30 minutes. Concentrate the mixture under reduced pressure, then dissolve in 1,2-dichloroethane (20 mL). Add N-[(1S)-2,2,2-trifluoro-1-(4-formylphenyl)-ethyl]-methanesulfonamide (150 mg, 0.53 mmol), acetic acid (0.05 mL, 0.87 mmol), and sodium triacetoxyborohydride (642.3 mg, 3.03 mmol). Stir the mixture at ambient temperature overnight. Concentrate under reduced pressure to give a residue and dilute the residue with MeOH (2 mL). Purify the residue via preparatory TLC using 10% MeOH in DCM to give a colorless oil. Dissolve the oil in MeOH (3 mL) and add HCl (1M in diethyl ether; 0.5 mL, 0.5 mmol) and stir for 30 minutes. Concentrate under reduced pressure to give the title compound as a white solid (10 mg, 3.7%). MS (m/z): 456 (M-Cl).

후처리

  1. concentrationConcentrate the mixture under reduced pressure
  2. dissolutiondissolve in 1,2-dichloroethane (20 mL)
  3. stirringStir the mixture at ambient temperature overnight
  4. concentrationConcentrate under reduced pressure
  5. customto give a residue
  6. customPurify the residue via preparatory TLC
  7. customto give a colorless oil
  8. stirringstir for 30 minutes
  9. concentrationConcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-43debd9f465440859e30a3aec58f84cc
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416138B2

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