Carbodiimide → HCID 178429240, compound

HRID 734676Notes

Reaction equation

HRID 734676 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:21])[CH2:5][CH:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:7]=1[C:8](O)=[O:9].[Cl:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([NH2:32])[CH:30]=2)[NH:25][N:24]=1.N=C=N>CN(C=O)C>[Cl:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([NH:32][C:8]([C:7]3[CH:6]([C:11]4[CH:20]=[CH:19][C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[CH:12]=4)[CH2:5][C:4](=[O:21])[NH:3][C:2]=3[CH3:1])=[O:9])[CH:30]=2)[NH:25][N:24]=1

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 160998652-Methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 178507360HCID 178507360, compound

Product 1

HCID 178429240HCID 178429240, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 1, Step 2 (100 mg, 0.36 mmol, 1.0 equiv) was combined with 3-chloro-1H-indazol-5-amine (90 mg, 0.53 mmol, 1.5 equiv) and PS-carbodiimide resin (0.994 mmol/g loading, 564 mg, 0.53 mmol, 1.5 equiv) in 5 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 ethyl acetate. The solution was washed with 0.5 N HCl, 0.5 N NaOH, and satd. NaCl. The organic layer was concentrated en vacuo. The residue was triturated with methylene chloride/methanol/ethyl acetate to provide 20 mg (13%) of the title compound as a light pink powder. MS (ES+) m/e 431 [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 ethyl acetate
  6. washThe solution was washed with 0.5 N HCl, 0.5 N NaOH
  7. concentrationThe organic layer was concentrated en vacuo
  8. customThe residue was triturated with methylene chloride/methanol/ethyl acetate

Sources & evidence

ORD record
ord-bcb7d03a265b4a2aa77a76fb28b46a3c
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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