HCID 66665651, compound → HCID 56645443, compound

HRID 872343Notes

Reaction equation

HRID 872343 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[C:25]([C:26]5[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=5)=[CH:24][CH:23]=[CH:22][N:21]4[C:33]=3[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C>Cl.O1CCOCC1>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:25]2[C:20]3[N:21]([C:33]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:8]5([NH2:7])[CH2:11][CH2:10][CH2:9]5)=[CH:13][CH:14]=4)[N:19]=3)[CH:22]=[CH:23][CH:24]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 66665651HCID 66665651, compound

Product 1

HCID 56645443HCID 56645443, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

81 mg (0.15 mmol) (1-{4-[8-(4-Fluorophenyl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert.-butyl ester, intermediate example Int-300-0, were dissolved in 7 mL 4 M hydrogen chloride in dioxane. The reaction mixture was stirred over night at room temperature. After evaporation of the solvent the residue was dissolved in methanol and purified by chromatography on silicagel (amine phase, eluents: methanol/ammonia) followed by an additional chromatography (amine phase, eluents: ethyl acetate/hexane) yielding 38.2 mg (55.2%) of the title compound.

Workup

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in methanol
  3. custompurified by chromatography on silicagel (amine phase, eluents: methanol/ammonia)

Sources & evidence

ORD record
ord-b6b460782f83412180b852338dc1ecd3
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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