HCID 67096903, compound → HCID 67098150, compound

HRID 2078666Notes

Reaction equation

HRID 2078666 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([O:45]C2CCCCO2)[CH2:9][N:10]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:34]=[C:33]4[C:29]([C:30]([C:38]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])=[O:39])=[CH:31][N:32]4[CH:35]([CH3:37])[CH3:36])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)C(=O)OC(C)(C)C)[CH:5]=[CH:6][CH:7]=1>CO.Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:45])[CH2:9][NH:10][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:34]=[C:33]4[C:29]([C:30]([C:38]([NH:40][S:41]([CH3:44])(=[O:42])=[O:43])=[O:39])=[CH:31][N:32]4[CH:35]([CH3:37])[CH3:36])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 67096903HCID 67096903, compound

Product 1

HCID 67098150HCID 67098150, compoundYield 153.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl [(2R)-2-(3-chlorophenyl)-2-(tetrahydro-2H-pyran-2-yloxy)ethyl][2-[4-[1-isopropyl-3-[[(methylsulfonyl)amino]carbonyl]-1H-indol-6-yl]phenyl]-ethyl]carbamate (132 mg), 10% hydrogen chloride in methanol (2 ml) and 4N hydrogen chloride in 1,4-dioxane (2 ml) was stirred at room temperature for 12 hours. The resulting mixture was evaporated under reduced pressure. The residue was purified by reverse phase column chromatography followed by treatment of 1N hydrochloric acid to give 6-[4-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-1-isopropyl-N-(methylsulfonyl)-1H-indole-3-carboxamide hydrochloride (81 mg).

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. customThe residue was purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-e3b8b8c19657406f81f070ea99db6217
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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