Carbodiimide → HCID 178429246, compound

HRID 734677Notes

Reaction equation

HRID 734677 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=O)=[C:4]([F:19])[CH:3]=1.[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH2:30])[CH:28]=2)[NH:23][N:22]=1.N=C=N>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:30][C:27]2[CH:28]=[C:29]3[C:24](=[CH:25][CH:26]=2)[NH:23][N:22]=[C:21]3[Cl:20])=[O:18])=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 688260574-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 178507360HCID 178507360, compound

Product 1

HCID 178429246HCID 178429246, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 3, Step 2 (103 mg, 0.36 mmol, 1.0 equiv) was combined with 3-chloro-1H-indazol-5-amine (91 mg, 0.54 mmol, 1.5 equiv) and PS-carbodiimide resin (0.994 mmol/g loading, 580 mg, 0.54 mmol, 1.5 equiv) in 6 mL of DMF and reacted overnight at room temperature. The reaction mixture was filtered and washed alternately with MeOH and CH2Cl2 (twice), then with diethyl ether. The filtrate was concentrated en vacuo and redissolved in EtOAc. The solution was washed with 0.5 N HCl, 0.5 N NaOH and satd. NaCl. The organic layer was concentrated en vacuo. Following purification by flash chromatography (0-50% EtOAc in CH2Cl2), the solid was triturated with CH2Cl2 to provide 10 mg (6.5%) of the title compound as light pink crystals. MS (ES+) m/e 434 [M+H]+.

Workup

  1. customreacted overnight at room temperature
  2. filtrationThe reaction mixture was filtered
  3. washwashed alternately with MeOH and CH2Cl2 (twice), then with diethyl ether
  4. concentrationThe filtrate was concentrated en vacuo
  5. dissolutionredissolved in EtOAc
  6. washThe solution was washed with 0.5 N HCl, 0.5 N NaOH and satd
  7. concentrationThe organic layer was concentrated en vacuo
  8. custompurification by flash chromatography (0-50% EtOAc in CH2Cl2)
  9. customthe solid was triturated with CH2Cl2

Sources & evidence

ORD record
ord-dffa402b97f34aa18284dc0ff571e967
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

Loading…