1,1'-Carbonyldiimidazole → HCID 68536364, compound

HRID 2374688Notes

Reaction equation

HRID 2374688 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=O)=[C:9]([F:16])[CH:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:31][C:32]1[C:40]([NH2:41])=[CH:39][CH:38]=[CH:37][C:33]=1[C:34]([NH2:36])=[O:35]>N1C=CC=CC=1.CN(C=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]2[NH:41][C:40]3[CH:39]=[CH:38][CH:37]=[C:33]([C:34]([NH2:36])=[O:35])[C:32]=3[N:31]=2)=[C:9]([F:16])[CH:8]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 534228072,3-Diaminobenzamide dihydrochlorideHCID 68533538HCID 68533538, compound

Product 1

HCID 68536364HCID 68536364, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of EXAMPLE 22B (770 mg, 3.4 mmol) in pyridine (5 mL) and N,N′-dimethylformamide (10 mL) was treated with 1,1′-carbonyldiimidazole (763 mg, 3.4 mmol) at 40° C. for 30 minutes. 2,3-Diaminobenzamide dihydrochloride (826 mg, 5.1 mmol) was added and the mixture stirred at ambient temperature overnight. The mixture was concentrated and the residue refluxed overnight in 20 mL of xylene and 2 mL of acetic acid. After cooling and concentration, the residue was purified by flash chromatography on silica gel using ethyl acetate to give the title compound (550 mg, 50%). MS (DCI/NH3) m/z 342 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. temperaturethe residue refluxed overnight in 20 mL of xylene
  3. temperatureAfter cooling
  4. concentrationconcentration
  5. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9b5e666957904556822f3929a1ac302d
Source dataset
uspto-grants-2008_12
Patent number
US07462724B2

Reaction notes

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