HCID 60142300, compound → HCID 68275978, compound

HRID 1475939Notes

Reaction equation

[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:31]([CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[C:13]3[CH:14]=[C:15]([C:18]([N:20]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1)[CH3:3]>C(Cl)(Cl)Cl.ClCCl.[O-2].[O-2].[Mn+4]>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:31]([CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[C:13]3[CH:14]=[C:15]([C:18]([N:20]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:19])[CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:8][CH:9]=1)(=[O:1])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-(4-(1-hydroxyethyl)phenyl)-N,N-diisopentyl-3-(3-(piperidin-1-yl)propyl)pyrazolo[1,5-a]pyridine-5-carboxamide (35 mg, 0.053 mmol) in chloroform (1 mL) was added activated manganese dioxide (92 mg, 1.06 mmol,) and the mixture was heated to 50° C. for 24 h. The reaction mixture was then diluted with dichloromethane and filtered through a 0.45 um filter, concentrated and then purified by preparative HPLC on a reverse-phase Zorbax SB-C18 column 21.2×100 mm eluted with MeOH-water-0.1% TFA. Isocratic 30% for 3 minutes then Gradient: 30% to 100% MeOH over 14 minutes. LCMS m/z 545.4 (M+H)+, ret. time=2.45 min.

Workup

filtrationfiltered through a 0.45 um
filtrationfilter
concentrationconcentrated
custompurified by preparative HPLC on a reverse-phase Zorbax
washcolumn 21.2×100 mm eluted with MeOH-water-0.1% TFA
waitGradient: 30% to 100% MeOH over 14 minutes

Sources & evidence

ORD record: ord-40ea910d35324259ad4a80db4df6b7f6
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018395B2

Reaction notes

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