Hydrochloric Acid → HCID 56646437, compound

HRID 872342Notes

Reaction equation

HRID 872342 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][N:21]4[C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl.[OH-].[Na+]>C(Cl)Cl.CO.O1CCOCC1>[CH3:27][O:26][C:24]1[CH:23]=[CH:22][N:21]2[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:18]([C:15]3[CH:14]=[CH:13][C:12]([C:8]4([NH2:7])[CH2:9][CH2:10][CH2:11]4)=[CH:17][CH:16]=3)[N:19]=[C:20]2[N:25]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66665421HCID 66665421, compound

Product 1

HCID 56646437HCID 56646437, compoundYield 50.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of crude {1-[4-(7-methoxy-3-phenyl-imidazo[1,2-a]pyrimidin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (550 mg) in DCM (3 mL) and methanol (1.9 mL) was added a solution of 4 M hydrogen chloride in dioxane (5.8 mL) and the mixture was stirred for 2 hours 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/methanol. The combined organic phases were washed with brine, dried and concentrated in vacuo. Purification was achieved by chromatography [silica; gradient elution: DCM to 8:2 DCM/ethanol] to give the title compound (220 mg).

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted three times
  3. additionwith a mixture of DCM/methanol
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. washwas achieved by chromatography [silica; gradient elution: DCM to 8:2 DCM/ethanol]

Sources & evidence

ORD record
ord-3a212a43515a42a4a61e72e654e445f9
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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