Sodium Bicarbonate → (S)-3-(1-(9H-purin-6-ylamino)ethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one

HRID 1502504

반응식

HRID 1502504 반응식
[CH:1]1([N:4]2[C:13]([C@@H:14]([NH:16][C:17]3[N:25]=[CH:24][N:23]=[C:22]4[C:18]=3[N:19]=[CH:20][N:21]4C3CCCCO3)[CH3:15])=[CH:12][C:11]3[C:6](=[C:7]([CH3:32])[CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:33])[CH2:3][CH2:2]1.C([O-])(O)=O.[Na+]>Cl.CCO>[N:25]1[C:17]([NH:16][C@H:14]([C:13]2[N:4]([CH:1]3[CH2:3][CH2:2]3)[C:5](=[O:33])[C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[CH3:32])[CH3:15])=[C:18]2[C:22]([NH:21][CH:20]=[N:19]2)=[N:23][CH:24]=1

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 580089832-cyclopropyl-8-methyl-3-((1S)-1-(9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one2회

생성물 1

HCID 178423765(S)-3-(1-(9H-purin-6-ylamino)ethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one수율 83.2%

시약·촉매·용매 1

HCID 21887872Ethanol hydrochloride용매

실험 절차

2-Cyclopropyl-8-methyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one (compound 5004) (222 mg, 0.5 mmol) was dissolved in HCl/EtOH (3 M, 5 mL) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized with saturated NaHCO3 solution to pH=7-8, and then extracted with CH2Cl2 (50 mL×3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was recrystallized from ethyl acetate and hexanes (1:1). The solid was collected by filtration and dried in vacuo to afford the desired product, (S)-3-(1-(9H-purin-6-ylamino)ethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one (5005, compound 200 in Table 4) (150 mg, 83% yield) as a white solid.

후처리

  1. extractionextracted with CH2Cl2 (50 mL×3)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was recrystallized from ethyl acetate and hexanes (1:1)
  7. filtrationThe solid was collected by filtration
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-9e457e180a5c416481fbab36d9f88f30
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206182B2

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