Sodium Bicarbonate → HCID 21192697, compound

HRID 1418395Notes

Reaction equation

HRID 1418395 reaction equation
O=[C:2]1[CH2:5][N:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.Cl.Cl.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:15]=1[C:16]([NH2:18])=[NH:17].C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:18][C:16]1[C:15]2[C:14](=[CH:22][CH:21]=[CH:20][C:19]=2[F:23])[NH:13][C:2]2([CH2:5][N:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]2)[N:17]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4595261HCID 4595261, compoundHCID 22008823HCID 22008823, compound

Product 1

HCID 21192697HCID 21192697, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 3-oxoazetidine-1-carboxylate (Y. Nitta, T. Yamagouchi, T. Tanaka; Heterocycles, 1986, 24, 25) (175 mg, 1.22 mmol) and 2-amino-6-fluorobenzamidine dihydrochloride (Example C, 280 mg, 1.22 mmol) in dry DMF (10 ml) were heated at 80° C. for 4 hours. The resulting solution was cooled and poured into aqueous sodium bicarbonate solution and the resulting mixture was extracted with ethyl acetate. The extracts were concentrated and the residue purified by flash chromatography on silica eluting with dichloromethane/methanol (10:1) to give the title compound as a solid (0.13 g) m.p. 210°-212° C.

Workup

  1. temperatureThe resulting solution was cooled
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. concentrationThe extracts were concentrated
  4. customthe residue purified by flash chromatography on silica eluting with dichloromethane/methanol (10:1)

Sources & evidence

ORD record
ord-82a093017dbf43259db028bfbe524804
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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