Hydrochloric Acid → HCID 178527274, compound

HRID 1711423Notes

Reaction equation

HRID 1711423 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[S:24]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:9]1)C1C=CC=CC=1.Cl>C1COCC1.CO.[Pd]>[C:27]1([S:24]([C:18]2[C:17]3[C:21](=[CH:22][CH:23]=[C:15]([O:14][CH:10]4[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)[CH:16]=3)[NH:20][N:19]=2)(=[O:25])=[O:26])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 178527275HCID 178527275, compound

Product 1

HCID 178527274HCID 178527274, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(1-benzylpiperidin-3-yloxy)-3-(1-naphthylsulfonyl)-1H-indazole (0.7 g, 1.4 mmoles), 10% Pd/C and concentrated HCl (1 mL) in THF and methanol was hydrogenated in a Parr hydrogenation bottle at 52 lb/in2 for 72 hours. TLC showed about 30% conversion into desired product. The reaction mixture was filtered through Celite, and the filtrate was concentrated. The concentrate, a mixture of starting material and product, was then separated by reverse phase chromatography on C18 column, using as eluent 10-100% H2O/AcCN, to afford the title compound as an off-white solid, 0.16 g, mp 178-180° C., identified by HNMR and mass spectral analyses, MS (ES) m/z 406.1.

Sources & evidence

ORD record
ord-0961d6ebc0c048ca98cf261d38cfdbb0
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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