Hydrogen Peroxide → HCID 10251737, 화합물

HRID 549275노트

반응식

HRID 549275 반응식
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.OO.FC(F)(F)C(O)=[O:37].[OH-:41].[Na+]>C(OCC)(=O)C.O>[ClH:31].[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([S:24]([C:21]2[CH:22]=[C:23]3[C:18]([CH:17]=[CH:16][N:15]=[C:14]3[N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:19][CH:20]=2)(=[O:37])=[O:41])=[CH:26][CH:27]=1

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67157202HCID 67157202, 화합물

생성물 1

HCID 10251737HCID 10251737, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

A mixture of 4-[7-(p-chloro-phenylsulfanyl)-isoquinolin-1-yl]-piperazine-1-carboxylic acid tert-butyl ester (297 mg, 0.65 mmol), H2O2 (30% in water, 0.5 mL), trifluoroacetic acid (3 mL) was heated at 50° C., 2 h. The reaction was continued overnight at 35° C. A water solution of NaOH (1N) was added (pH=14), ethyl acetate was added and the organic phase was separated, dried (MgSO4), filtered. The filtrated was concentrated and the residue was purified by flash column chromatography (SiO2, dichloromethane:methanol 9.5:0.5→9.0:1.0) The free base was converted into hydrochloride by treatment with HCl in diethyl ether to obtained 70 mg of the title compound. 1H NMR (CH3OH-d4) δ 8.75-8.85 (m, 2H), 8.10-8.25 (m, 3H), 8.00-8.08 (m, 2H), 7.60-7.68 (m, 3H), 3.85-3.95 (m, 4H), 3.55-3.65 (m, 4H).

후처리

  1. additionwas added
  2. customthe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrated was concentrated
  6. customthe residue was purified by flash column chromatography (SiO2, dichloromethane:methanol 9.5:0.5→9.0:1.0) The free base

출처 및 근거

ORD 기록
ord-8c1b1de219fb4cc597654e6cc0d1a860
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943639B2

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