HCID 59153119, compound → HCID 59153001, compound

HRID 1095851Notes

Reaction equation

HRID 1095851 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([N:15]([S:17]([C:20]3[CH:21]=[N:22][C:23]([O:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)=[C:24]([C:26]([CH3:28])=[CH2:27])[CH:25]=3)(=[O:19])=[O:18])[CH3:16])[C:9]=2[CH:8]=[N:7]1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:37])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([N:15]([S:17]([C:20]3[CH:21]=[N:22][C:23]([O:29][C:30]4[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=4)=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:25]=3)(=[O:18])=[O:19])[CH3:16])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

4

Reactant 1

HCID 59153119HCID 59153119, compound

Product 1

HCID 59153001HCID 59153001, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ((R)-4-{[6-(4-chloro-phenoxy)-5-isopropenyl-pyridine-3-sulfonyl]-methyl-amino}-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (42 mg, 0.077 mmol) in methanol was hydrogenated over 10% palladium on carbon (6 mg) under atmospheric pressure for 2.5 hours at room temperature. The reaction mixture was filtered through a glass funnel and the filtrate was purified by preparative HPLC to afford ((R)-4-{[6-(4-chloro-phenoxy)-5-isopropyl-pyridine-3-sulfonyl]-methyl-amino}-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (22.4 mg, 53%) as a white solid. MS cald. for C26H31ClN4O5S 546, obsd. (ESI+) [(M+H)+] 547.

Workup

  1. filtrationThe reaction mixture was filtered through a glass funnel
  2. customthe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-272b195716ca4831bbb8eefc4c936fc5
Source dataset
uspto-grants-2012_03
Patent number
US08138208B2

Reaction notes

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