Oxalic Acid → 5-AMINO-6-CHLORO-2-ETHYL-N-{[1-(2-HYDROXYBUTYL)PIPERIDIN-4-YL]METHYL}IMIDAZO[1,2-a]PYRIDINE-8-CARBOXAMIDE OXALATE

HRID 965810Notes

Reaction equation

HRID 965810 reaction equation
[NH2:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH3:12])[N:10]=[C:6]2[C:5]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH:24]([OH:27])[CH2:25][CH3:26])[CH2:19][CH2:18]2)=[O:14])=[CH:4][C:3]=1[Cl:28].[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>CO>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[NH2:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH3:12])[N:10]=[C:6]2[C:5]([C:13]([NH:15][CH2:16][CH:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH:24]([OH:27])[CH2:25][CH3:26])[CH2:21][CH2:22]2)=[O:14])=[CH:4][C:3]=1[Cl:28]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 103413815-amino-6-chloro-2-ethyl-N-{[1-(2-hydroxybutyl)piperidin-4-yl]methyl}-imidazo[1,2-a]pyridine-8-carboxamide

Product 1

HCID 223132655-AMINO-6-CHLORO-2-ETHYL-N-{[1-(2-HYDROXYBUTYL)PIPERIDIN-4-YL]METHYL}IMIDAZO[1,2-a]PYRIDINE-8-CARBOXAMIDE OXALATEYield 142.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-amino-6-chloro-2-ethyl-N-{[1-(2-hydroxybutyl)piperidin-4-yl]methyl}-imidazo[1,2-a]pyridine-8-carboxamide (Example 13, Step 3, 79 mg, 0.19 mmol) was dissolved in methanol (3 mL) and acidified with oxalic acid (17.4 mg, 0.13 mmol) in methanol (2 mL). The mixture was then concentrated and a white precipitate was washed with ethyl acetate to afford (92 mg, 80%) of the title compound.

Workup

  1. concentrationThe mixture was then concentrated
  2. washa white precipitate was washed with ethyl acetate

Sources & evidence

ORD record
ord-51e857823e564950b4b992938bd17c0f
Source dataset
uspto-grants-2005_10
Patent number
US06951867B2

Reaction notes

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