Hydrochloric Acid → 1-[4-(5-Methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutanamine

HRID 872366Notes

Reaction equation

HRID 872366 reaction equation
[CH3:1][C:2]1[N:7]2[C:8]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4([NH:21]C(=O)OC(C)(C)C)[CH2:20][CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>C(Cl)Cl.CO.O1CCOCC1>[CH3:1][C:2]1[N:7]2[C:8]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4([NH2:21])[CH2:20][CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86691044Tert-butyl {1-[4-(5-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 666656671-[4-(5-Methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutanamineYield 41.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of crude tert-butyl {1-[4-(5-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl}carbamate (49 mg) in DCM (0.42 mL) and methanol (0.26 mL) was added a solution of 4 M hydrogen chloride in dioxane (0.54 mL) and the mixture was stirred overnight at rt. The mixture was poured onto ice, made alkaline with aqueous sodium hydroxide (2 N) and extracted three times with a mixture of DCM. The combined organic phases were washed with brine, dried and concentrated in vacuo to give 16 mg of the title compound in 42% overall yield.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted three times
  3. additionwith a mixture of DCM
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d055fd3cf7ce4d48853909c1f92fb0a2
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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