1,1'-Carbonyldiimidazole → HCID 86636675, compound

HRID 2075391Notes

Reaction equation

HRID 2075391 reaction equation
[F:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]([OH:14])=O)=[CH:7][CH:6]=2.N1(C(N2C=CN=C2)=O)C=CN=C1.[NH2:27][NH:28][C:29]([NH2:31])=[S:30]>CN(C=O)C>[F:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]([NH:27][NH:28][C:29]([NH2:31])=[S:30])=[O:14])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2723789ThiosemicarbazideHCID 57991948HCID 57991948, compound

Product 1

HCID 86636675HCID 86636675, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-fluoroisoquinoline-6-carboxylic acid (0.71 g, 3.72 mmol) and di(1H-imidazol-1-yl)methanone (1.21 g, 7.44 mmol) in DMF (9.0 mL) was stirred at room temperature for 1 hour and 20 minutes until no gas was evolved. The reaction mixture was heated at 70° C. for 40 minutes. Thiosemicarbazide (1.02 g, 11.2 mmol) was added, and the reaction mixture was stirred at 70° C. for another 30 minutes. The solvents were removed under reduced pressure. HCl (1.0 N, 50 mL) was added, and the solids were recovered by filtration, and washed with water to provide the product as an off-white solid (0.86 g, 89%). LCMS (API-ES) m/z: 265 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated at 70° C. for 40 minutes
  2. stirringthe reaction mixture was stirred at 70° C. for another 30 minutes
  3. customThe solvents were removed under reduced pressure
  4. additionHCl (1.0 N, 50 mL) was added
  5. filtrationthe solids were recovered by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-58a54495633c45f79e5a27cb056eb974
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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