HCID 58724509, compound → HCID 58724420, compound

HRID 1844961Notes

Reaction equation

HRID 1844961 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([C:9]1[C:17]2[N:16]=[C:15]([NH:18][C:19]([C:21]3[N:22]=[CH:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:20])[NH:14][C:13]=2[CH:12]=[C:11]([N+:31]([O-])=O)[CH:10]=1)=[O:8]>CN(C=O)C.C(O)(=O)C.[Pd]>[NH2:31][C:11]1[CH:10]=[C:9]([C:7](=[O:8])[NH:6][C:2]2[NH:3][CH:4]=[CH:5][N:1]=2)[C:17]2[N:16]=[C:15]([NH:18][C:19]([C:21]3[N:22]=[CH:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:20])[NH:14][C:13]=2[CH:12]=1

Participants

5

Reactant 1

HCID 58724509HCID 58724509, compound

Product 1

HCID 58724420HCID 58724420, compoundYield 103.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

0.1 g (0.2 mmol) of isoquinoline-3-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-6-nitro-1H-benzoimidazol-2-yl]-amide (Example 129) was suspended in a mixture of 2 mL of DMF and 5 mL of acetic acid. To this stirring solution, −20 mg of 10% Pd on carbon was added, and the resulting mixture was hydrogenated at 42 psi of H2 at room temperature for 3.0 h. The reaction mixture was filtered, and the solid was washed with 5 mL of DMF. The filtrate and washings were combined and evaporated to reduce the volume to 10 mL, then diluted with saturated NaHCO3 (10 mL), and extracted with ethyl acetate. The organic layer was washed with water and brine and evaporated to provide 85 mg (91%) of isoquinoline-3-carboxylic acid [6-amino-4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 413 (M+1)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with 5 mL of DMF
  3. customevaporated
  4. additiondiluted with saturated NaHCO3 (10 mL)
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. customevaporated

Sources & evidence

ORD record
ord-6d289075e522457c9b5e6bfb5cdd0969
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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