Tetrahydrofuran → 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-(4-fluorophenyl)-1H-imidazole-4-carboxylic acid

HRID 2356598Notes

Reaction equation

HRID 2356598 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[NH:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[O:21]1[C:26]2C=CC(N)=[CH:30][C:25]=2OCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].FC1C=CC(C#N)=CC=1.[O:51]1CCCC1>[Cl-].[Na+].O.ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH:30]=[C:25]([C:26]([OH:51])=[O:21])[N:13]=[C:12]3[C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 145174-FluorobenzonitrileHCID 891481,4-Benzodioxan-6-ylamineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178511896HCID 178511896, compound

Product 1

HCID 593841571-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-(4-fluorophenyl)-1H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-fluorobenzenecarboxamidine To a solution of 2.39 g (15.8 mmol) of 1,4-benzodioxan-6-amine in 30 mL of tetrahydrofuran at ambient temperature was added 8.7 ml (17.4 mmol) of 2.0 M (in tetrahydrofuran) sodium bis(trimethylsilyl)amide and the resulting solution was stirred for 20 min. To this reaction mixture was added 1.91 g (15.8 mmol) of 4-fluorobenzonitrile all at once. The resulting mixture was stirred at ambient temperature overnight and then poured into brine (50 mL) and dichloromethane (150 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as yellow solid which was used without further purification. LC/MS 273.2 (M+1).

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature overnight
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-153aa86d20e04f02b3c7fffa45246944
Source dataset
uspto-grants-2010_07
Patent number
US07759352B2

Reaction notes

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