HCID 178496925, compound → HCID 178496924, compound

HRID 44007Notes

Reaction equation

HRID 44007 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([C:16]1[C:17]([OH:36])=[CH:18][C:19]2[N:20]([N:22]=[C:23]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:24]=2[C:25]([O:27][CH3:28])=[O:26])[CH:21]=1)[S:12]([CH3:15])(=[O:14])=[O:13])(C(C)(C)C)(C)C>[Pd].C(OCC)(=O)C>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:23]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:19]3[CH:18]=[C:17]([OH:36])[C:16]([N:11]([CH2:10][CH2:9][OH:8])[S:12]([CH3:15])(=[O:14])=[O:13])=[CH:21][N:20]3[N:22]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 178496925HCID 178496925, compound

Product 1

HCID 178496924HCID 178496924, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing Methyl 6-(N-(2-(tert-butyldimethylsilyloxy)ethyl)methylsulfonamido)-2-(4-fluorophenyl)-5-hydroxypyrazolo[1,5-a]pyridine-3-carboxylate (0.17 g, 0.27 mmol) and ethyl acetate (5.4 mL) was added 10% Pd/C (0.04 g, 0.04 mmol Pd) in one portion under a nitrogen atmosphere. The reaction mixture was stirred for 2 h under an atmosphere of hydrogen gas (balloon), filtered and concentrated to afford Methyl 2-(4-fluorophenyl)-5-hydroxy-6-(N-(2-hydroxyethyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxylate as a light yellow oil. 1H NMR (400 MHz, DMSO-D6) δ ppm 11.71 (s, 1H), 8.68 (s, 1H), 7.73 (ddd, J=11.98, 5.33, 2.76 Hz, 2H), 7.46 (s, 1H), 7.25-7.31 (m, 2H), 3.70 (s, 7H), 3.11-3.14 (m, 3H), 0.74 (s, 9H), −0.06-−0.04 (m, 6H). LCMS: retention time: 2.750 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters-Sunfire, 5 micron, C18, 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN/90% H2O/10 mM TFA and solvent B was 10% H2O/90% CH3CN/10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 538 (MH+).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-90c2f0e47a614fa09ad920559cc89fae
Source dataset
uspto-grants-2013_09
Patent number
US08536338B2

Reaction notes

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