1,1'-Carbonyldiimidazole → HCID 10355726, compound

HRID 1454924Notes

Reaction equation

HRID 1454924 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CN(C)C=O>[N:29]1([CH2:28][CH2:27][CH2:26][NH:25][C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:12])[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78250Indazole-3-carboxylic acidHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 10355726HCID 10355726, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Indazole-3-carboxylic acid (810 mg, 5 mmol) is heated at 60° C. in the presence of carbonyldiimidazole (891 mg, 5.5 mmol) in N,N-dimethylformamide (DMF) (14 ml) under argon for 3 h. 1-(3-Aminopropyl)-imidazole (597 μl, 5 mmol) in solution in DMF (2 ml) is added and the mixture is heated for 2 h and 20 min at 60° C. After cooling, the DMF is evaporated under vacuum to give a yellow oil which is chromatographed on 54 g of silica. The compound obtained is eluted with an ethyl acetate (AcOEt)/methanol (MeOH) (9/1) mixture.

Workup

  1. temperatureAfter cooling
  2. customthe DMF is evaporated under vacuum
  3. customto give a yellow oil which
  4. customis chromatographed on 54 g of silica
  5. customThe compound obtained
  6. washis eluted with an ethyl acetate (AcOEt)/methanol (MeOH) (9/1) mixture

Sources & evidence

ORD record
ord-c6ebf7466b294cf986559683937abcf8
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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