Hydrogen Peroxide → HCID 9981615, compound

HRID 549274Notes

Reaction equation

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]

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

additionwas added
customthe organic phase was separated
dry with materialdried (MgSO4)
filtrationfiltered
concentrationThe filtrated was concentrated
customthe residue was purified by flash column chromatography (SiO2, dichloromethane:methanol 9:1) The free base

Sources & evidence

ORD record: ord-303c2d1741a74f55964f67b923716317
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943639B2

Reaction notes

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