Hydrochloric Acid → HCID 178523835, compound

HRID 406292Notes

Reaction equation

HRID 406292 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][C@H:10]1[CH2:13][C@H:12]([NH:14][C:15]([C:17]2[C:18]3[N:19]([CH:28]=[CH:29][N:30]=3)[C:20]([CH2:23][O:24]COC)=[CH:21][CH:22]=2)=[O:16])[CH2:11]1.Cl>C1COCC1.CC(O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][C@H:10]1[CH2:13][C@H:12]([NH:14][C:15]([C:17]2[C:18]3[N:19]([CH:28]=[CH:29][N:30]=3)[C:20]([CH2:23][OH:24])=[CH:21][CH:22]=2)=[O:16])[CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 178499437HCID 178499437, compound

Product 1

HCID 178523835HCID 178523835, compoundYield 400.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of N-{trans-3-[(2,3-dichlorophenyl)oxy]cyclobutyl}-5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxamide (598 mg, 1.328 mmol) in THF (5 mL) was added 5 to 6M HCl in 2-propanol (5 mL, 27.5 mmol) and a clear solution was observed. The reaction mixture was stirred under a nitrogen atmosphere at room temperature for 1 hour. More 5-6M HCl in 2-propanol (0.5 mL) was added and stirring continued for another hour when HPLC indicated the reaction to be complete. The mixture was concentrated in vacuo to give a colourless gum (2.163 g). This material was partitioned between ethyl acetate (30 mL) and sodium bicarbonate (2×15 mL). The organic phase was separated, washed with brine (15 mL), dried over magnesium sulphate and evaporated in vacuo to give the title compound as a yellow solid (537 mg).

Workup

  1. stirringstirring
  2. waitcontinued for another hour
  3. customthe reaction
  4. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3a86e154822c41d28f724c4c188c9e54
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

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