Hydrogen Peroxide → HCID 9981615、化合物

HRID 549274ノート

反応式

HRID 549274 の反応式
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])=[C:27]([Cl:32])[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:38].[OH-:42].[Na+]>C(OCC)(=O)C.O>[ClH:31].[Cl:32][C:27]1[CH:26]=[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:38])=[O:42])[CH:30]=[CH:29][C:28]=1[Cl:31]

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67156369HCID 67156369、化合物

生成物 1

HCID 9981615HCID 9981615、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A mixture of 4-[7-(3,4-dichloro-phenylsulfanyl)-isoquinolin-1-yl]-piperazine-1-carboxylic acid tert-butyl ester (230 mg, 0.47 mmol), H2O2 (30% in water, 0.5 mL), trifluoroacetic acid (1.5 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 9:1) The free base was converted into hydrochloride by treatment with HCl in diethyl ether to obtained 45 mg of the title compound. 1H NMR (CH3OH-d4) δ 8.75-8.85 (m, 1H), 8.10-8.30 (m, 4H), 7.90-8.00 (m, 1H), 7.75-7.85 (m, 1H), 7.50-7.60 (m, 1H), 3.85-3.90 (m, 4H), 3.50-3.70 (m, 4H).

後処理

  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 9:1) The free base

出典と根拠

ORDレコード
ord-303c2d1741a74f55964f67b923716317
出典データセット
uspto-grants-2011_05
特許番号
US07943639B2

反応ノート

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