1,1'-Carbonyldiimidazole → HCID 46206098, compound

HRID 2366453Notes

Reaction equation

HRID 2366453 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[C:4]([F:11])[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[NH2:26][C:27]1[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([NH2:31])=[O:30]>N1C=CC=CC=1.CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[NH:36][C:35]3[CH:34]=[CH:33][CH:32]=[C:28]([C:29]([NH2:31])=[O:30])[C:27]=3[N:26]=2)=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3026814-Bromo-2-fluorobenzoic acidHCID 534228072,3-Diaminobenzamide dihydrochloride

Product 1

HCID 46206098HCID 46206098, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

4-Bromo-2-fluorobenzoic acid (5 g) in a mixture of pyridine (50 mL) and DMF (50 mL) at 45° C. was treated with CDI (0.856 g), stirred at 45° C. for 1 hour, treated with 2,3-diaminobenzamide dihydrochloride (5.1 g), stirred at ambient temperature for 18 hours and concentrated. The concentrate was dissolved in acetic acid (100 mL), heated at 70° C. for 1 hour and concentrated. The concentrate was partitioned between ethyl acetate and sodium bicarbonate solution and the organic phase was isolated, washed with brine and concentrated. The concentrate was flash chromatographed on silica gel with ethyl acetate.

Workup

  1. stirringstirred at ambient temperature for 18 hours
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in acetic acid (100 mL)
  4. temperatureheated at 70° C. for 1 hour
  5. concentrationconcentrated
  6. customThe concentrate was partitioned between ethyl acetate and sodium bicarbonate solution
  7. customthe organic phase was isolated
  8. washwashed with brine
  9. concentrationconcentrated
  10. customchromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-5e4343a074114417a6b36c56839e3f05
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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