1,1'-Carbonyldiimidazole → 4-(3-bromo-4-fluorophenyl)-3-(4-(2-methoxyethylamino)-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5(4H)-one

HRID 69757

Reaction equation

HRID 69757 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:13]2[C:17]([NH:18][CH2:19][CH2:20][O:21][CH3:22])=[N:16][O:15][N:14]=2)=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[C:23](=[O:24])[O:12][N:11]=[C:10]2[C:13]2[C:17]([NH:18][CH2:19][CH2:20][O:21][CH3:22])=[N:16][O:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178495897HCID 178495897, compound

Product 1

HCID 666056984-(3-bromo-4-fluorophenyl)-3-(4-(2-methoxyethylamino)-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5(4H)-oneYield 98.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidamide (76.5 g, 0.204 mol), 1,1′-carbonyldiimidazole (49.7 g, 0.307 mol), and ethyl acetate (720 mL) was heated to 60° C. and stirred for 20 min. LCMS indicated reaction completed. The reaction was cooled to room temperature, washed with 1N HCl (2×750 mL), dried over sodium sulfate, and concentrated to give the desired product (80.4 g, 98%) as a crude brown solid. LCMS for C13H12BrFN5O4 (M+H)+: m/z=400.0, 402.0. 1H NMR (400 MHz, DMSO-d6): δ 7.94 (t, J=8.2 Hz, 1 H), 7.72 (dd, J=9.1, 2.3 Hz, 1 H), 7.42 (m, 1 H), 6.42 (t, J=5.7 Hz, 1 H), 3.46 (t, J=5.4 Hz, 2 H), 3.36 (t, J=5.8 Hz, 2 H), 3.26 (s, 3 H).

Workup

  1. customreaction
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with 1N HCl (2×750 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cb4382b372044a8ab1ee0b2caa0c406f
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Linked notes

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