1,1'-Carbonyldiimidazole → HCID 66606496, compound

HRID 69788Notes

Reaction equation

HRID 69788 reaction equation
[OH:1][N:2]=[C:3]([C:15]1[C:19]([NH:20][CH2:21][CH2:22][O:23][CH3:24])=[N:18][O:17][N:16]=1)[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1.[C:25](N1C=CN=C1)(N1C=CN=C1)=[O:26]>C(OCC)(=O)C>[CH3:24][O:23][CH2:22][CH2:21][NH:20][C:19]1[C:15]([C:3]2[N:4]([C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:13])([F:14])[F:12])[CH:6]=3)[C:25](=[O:26])[O:1][N:2]=2)=[N:16][O:17][N:18]=1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 178495896N'-hydroxy-4-[(2-methoxyethyl)amino]-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide

Product 1

HCID 66606496HCID 66606496, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

N′-Hydroxy-4-[(2-methoxyethyl)amino]-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide (1.4 g, 3.80 mmol) and 1,1′-carbonyldiimidazole (1.16 g, 7.16 mmol) were dissolved in ethyl acetate (20 mL). The reaction mixture was heated at 70° C. for 40 minutes. Additional 1,1′-carbonyldiimidazole (0.26 g, 1.16 mmol) was added. After stirring at 70° C. for another 50 minutes, the reaction was allowed to cool to room temperature. Ethyl acetate (20 mL) was added and the crude reaction was washed with 1N HCl in water (2×20 mL). Brine was added to aid in the separation of the first wash. The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel with an eluent of ethyl acetate in hexanes gave the desired product (1.3 g, 90%). LCMS calculated for C14H13F3N5O4 (M+H)+: m/z=372.0. 1H NMR (400 MHz, DMSO-d6): δ 8.07 (s, 1H), 7.92 (m, 2H), 7.79 (t, J=8.1 Hz, 1H), 6.42 (t, J=6.0 Hz, 1H), 3.47 (t, J=5.8 Hz, 2H), 3.38 (q, J=5.0 Hz, 2H), 3.24 (s, 3H).

Workup

  1. temperatureto cool to room temperature
  2. customthe crude reaction
  3. washwas washed with 1N HCl in water (2×20 mL)
  4. additionBrine was added to aid in the separation of the first wash
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel with an eluent of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-877de82a1a764275ac213941ccea3e6e
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Reaction notes

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