Water → N-[2-({1-[1-(4-Chlorophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinolin-6-yl}oxy)ethyl]propane-1-sulfonamide hydrochloride

HRID 242069노트

반응식

HRID 242069 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])=[CH:19][CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O.[BH4-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])=[CH:19][CH:20]=4)[CH2:15][CH2:14][NH:13]3)[CH2:9][CH2:10][CH2:11]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58246191N-[2-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-6-yl}oxy)ethyl]propane-1-sulfonamide

생성물 1

HCID 66869450N-[2-({1-[1-(4-Chlorophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinolin-6-yl}oxy)ethyl]propane-1-sulfonamide hydrochloride

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

N-[2-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-6-yl}oxy)ethyl]propane-1-sulfonamide (320 mg, 0.62 mmol) was dissolved in methanol (5 mL) and water (0.1 mL) and sodiumborohydride (47 mg, 1.25 mmol) was added at 4° C. in small portions. The reaction mixture was allowed to warm to room temperature and stirring was continued over night. The solvent was evaporated in vacuo, the residue was treated with dichloromethane and water. The aqueous layer was extracted several times with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by preparative HPLC (RP, acetonitrile, water). The purified amine was then converted into the corresponding hydrochloric acid salt by adding 5M isoporpanolic hydrochloric acid followed by concentration in vacuo. Yield: 35 mg (0.07 mmol, 11%, colorless solid).

후처리

  1. waitwas continued over night
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was treated with dichloromethane and water
  4. extractionThe aqueous layer was extracted several times with dichloromethane
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by preparative HPLC (RP, acetonitrile, water)
  8. additionby adding 5M isoporpanolic hydrochloric acid
  9. concentrationfollowed by concentration in vacuo

출처 및 근거

ORD 기록
ord-f056898c5880418ba50e0811d5f474fb
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653100B2

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