Hydrochloric Acid → HCID 56646040, compound

HRID 872341Notes

Reaction equation

HRID 872341 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]=[CH:24][CH:23]=[CH:22][N:21]4[C:26]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl.[OH-].[Na+]>C(Cl)Cl.CO.O1CCOCC1>[C:27]1([C:26]2[N:21]3[CH:22]=[CH:23][CH:24]=[N:25][C:20]3=[N:19][C:18]=2[C:15]2[CH:14]=[CH:13][C:12]([C:8]3([NH2:7])[CH2:11][CH2:10][CH2:9]3)=[CH:17][CH:16]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66665999HCID 66665999, compound

Product 1

HCID 56646040HCID 56646040, compoundYield 7.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of crude {1-[4-(3-phenyl-imidazo[1,2-a]pyrimidin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (390 mg) in DCM (0.9 mL) and methanol (0.57 mL) was added a solution of 4 M hydrogen chloride in dioxane (1.77 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/methanol. The combined organic phases were washed with brine, dried and concentrated in vacuo to give the crude title compound as a yellow oil. Purification was achieved by chromatography [amino phase silica; gradient elution: hexane to EtOAc], followed by trituration with diisopropylether at 0° C. to give the title compound (21.9 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. customto give the crude title compound as a yellow oil
  8. customPurification
  9. washwas achieved by chromatography [amino phase silica; gradient elution: hexane to EtOAc]
  10. customfollowed by trituration with diisopropylether at 0° C.

Sources & evidence

ORD record
ord-c827a01413bb46aea6d83b7ecf851503
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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