1,1'-Carbonyldiimidazole → HCID 135508085, compound

HRID 2117043Notes

Reaction equation

HRID 2117043 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:19]3[CH2:25][CH:24]4[N:26]([CH3:27])[CH:21]([CH2:22][CH2:23]4)[CH2:20]3)[C:10]3[C:15]([O:16][C:17]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[NH:4].[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29]>O1CCOCC1>[CH3:27][N:26]1[CH:21]2[CH2:22][CH2:23][CH:24]1[CH2:25][CH:19]([N:9]1[C:8]3[CH:7]=[CH:6][C:5]([C:3]4[NH:4][C:28](=[O:29])[O:1][N:2]=4)=[CH:18][C:17]=3[O:16][C:15]3[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:20]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178479853HCID 178479853, compound

Product 1

HCID 135508085HCID 135508085, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of N-Hydroxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxamidine, 1 h (0.66 g; 1.81 mmol) in dioxane (20 mL) was added 1,1′-carbonyldiimidazole (0.44 g; 2.71 mmol), and the mixture was stirred at 110° C. for 4 h. The mixture was allowed to cool to rt, and the solvent was evaporated. The residue was purified via reverse phase HPLC (eluent gradient: 20 to 45% CH3CN in H2O containing 0.1% TFA) to yield 161 mg (17.6%) of title compound 3-[10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazin-3-yl]-4H-[1,2,4]oxadiazol-5-one, 2h as a TFA salt. MS m/z (MH+) 390.9.

Workup

  1. temperatureto cool to rt
  2. customthe solvent was evaporated
  3. customThe residue was purified via reverse phase HPLC (eluent gradient: 20 to 45% CH3CN in H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-f3883d3bebde4b9fb977760f87a8a472
Source dataset
uspto-grants-2008_10
Patent number
US07439239B2

Reaction notes

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