Acetic Acid → {1-[4-(6-Phenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362156Notes

Reaction equation

HRID 2362156 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20]N(C)C)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:32][C:33]1[NH:34][CH:35]=[CH:36][N:37]=1.CC(O)=O.CCO>C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][N:34]4[CH:35]=[CH:36][N:37]=[C:33]4[N:32]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 821402-AminoimidazoleHCID 66719111HCID 66719111, compound

Product 1

HCID 66668862{1-[4-(6-Phenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl EsterYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 1 (1.2 g, 2.9 mmol) and 2-aminoimidazole (0.77 g 4.3 mmol) were added into a solution of AcOH (2 mL) and EtOH (10 mL). The mixture was heated to reflux and stirred overnight. The solution was cooled to r.t. and diluted with 30 mL of DCM. The organic phase was washed with 0.1N HCl(aq) and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to give 1.2 g of 4-1 as a yellow solid. MS (ESI) m/e (M+H+): 441.3

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. washThe organic phase was washed with 0.1N HCl(aq) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-28a65aacbe9f4cbda96d52e036d0cbce
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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