N-[2-(4-benzyloxycarbonylamino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide oxalate → N-[2-(4-amino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide dioxalate

HRID 482584Notes

Reaction equation

HRID 482584 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].C(OC([NH:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][NH:26][C:27]([C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]([CH:38]([CH3:40])[CH3:39])[N:30]=2)=[O:28])[CH2:20][CH2:19]1)=O)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[NH2:17][CH:18]1[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][NH:26][C:27]([C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]([CH:38]([CH3:40])[CH3:39])[N:30]=2)=[O:28])[CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 18969263N-[2-(4-benzyloxycarbonylamino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide oxalateHCID 178418361HCID 178418361, compound

Product 1

HCID 86751129N-[2-(4-amino-1-piperidinyl)ethyl]-1-(2-propyl)-1H-indazole-3-carboxamide dioxalate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from Example 8, as the free base (8.71 g, 18.8 mmol), was reacted with hydrogen gas in the presence of 5% Pd/C (25° C./18 h/60 PSI) in an ethanol solution. After filtering the catalyst, the ethanol was evaporated to 5.0 g oil. Crystallization as the dioxalate salt from methanol/water provided colorless crystals. Mp 232° C. Mass spectrum, m+ =329. Anal (C22H31N5O9) theory C, 51.86; H, 6.13; N, 13.75; found C, 51.61; H, 6.04; N, 13.48.

Workup

  1. filtrationAfter filtering the catalyst
  2. customthe ethanol was evaporated to 5.0 g oil
  3. customCrystallization as the dioxalate salt from methanol/water provided colorless crystals

Sources & evidence

ORD record
ord-5eac0f61743643a9befa82f0be2d13c5
Source dataset
uspto-grants-1998_08
Patent number
US05798367

Reaction notes

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