5-Chloro-2-fluorobenzene-1-carboximidamide → HCID 178517511, compound

HRID 1354327Notes

Reaction equation

HRID 1354327 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[NH:5].C([O:14][C:15]([CH:17]1[C:21](=O)[CH2:20][CH2:19][O:18]1)=O)C>CCO>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([C:4]2[N:6]=[C:15]([OH:14])[C:17]3[O:18][CH2:19][CH2:20][C:21]=3[N:5]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 219309795-Chloro-2-fluorobenzene-1-carboximidamideHCID 450902902-Furancarboxylicacid,tetrahydro-3-oxo-,ethylester(9CI)

Product 1

HCID 178517511HCID 178517511, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 2-fluoro-5-chlorobenzamidine (1.05 g, 6.08 mmol, 1.2 eq) in EtOH (20 ml) was added 3-oxo-tetrahydrofuran-2-carboxylic acid ethyl ester (prepared according to Moyer, M. P; Feldman, P. L.; Rapoport, H. J. Org. Chem, 1985, 50, 5223-5230; 800 mg, 5.06 mmol, 1 eq) in ethanol (5 ml). The reaction mixture was heated to 80° C. overnight. The reaction mixture was cooled to rt and the crude residue was purified by flash column chromatography (5% MeOH in CHCl3) to afford a white solid 2-(5-chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidin-4-ol (650 mg, 53%).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe crude residue was purified by flash column chromatography (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-09175061d59d43e4a1d46b04d32c5c84
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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