Hydrochloric Acid → HCID 67610940, compound

HRID 1418391Notes

Reaction equation

HRID 1418391 reaction equation
C1O[C:4]2([CH2:9][CH2:8][N:7]([C:10]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)=[O:11])[CH2:6][CH2:5]2)OC1.[ClH:18].Cl.[NH2:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:22]=1[C:23]([NH2:25])=[NH:24].Cl>C(O)C>[ClH:18].[NH2:25][C:23]1[C:22]2[C:21](=[CH:29][CH:28]=[CH:27][C:26]=2[F:30])[NH:20][C:4]2([CH2:5][CH2:6][N:7]([C:10]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)=[O:11])[CH2:8][CH2:9]2)[N:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12185909HCID 12185909, compoundHCID 22008823HCID 22008823, compound

Product 1

HCID 67610940HCID 67610940, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

1-(1H-Imidazol-1-ylcarbonyl)-4-piperidone ethylene ketal (Example EE, 156 mg., 0.66 mmol) was added to 2-amino-6-fluorobenzamidine dihydrochloride (150 mg, 0.66 is mmol) in ethanol (10 ml) together with an excess of HCl (1M in ether). This mixture was heated to 55° C. overnight, concentrated in vacuo and purified by flash column chromatography eluting with dichloromethane, increasing the gradient to dichloromethane/methanol (10:1), to give a solid which triturated from ethanol/ether to give yellow crystals, m.p. 260° C. (dec.).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by flash column chromatography
  3. washeluting with dichloromethane
  4. temperatureincreasing the gradient to dichloromethane/methanol (10:1)
  5. customto give a solid which
  6. customtriturated from ethanol/ether
  7. customto give yellow crystals, m.p. 260° C. (dec.)

Sources & evidence

ORD record
ord-e458bfbb3c15431aa15886bf6867d3ee
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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