Carbodiimide → HCID 178429248, compound

HRID 734675Notes

Reaction equation

HRID 734675 reaction equation
[F: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)=[CH:4][CH:3]=1.[Cl:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([NH2:29])[CH:27]=2)[NH:22][N:21]=1.N=C=N>CN(C=O)C>[Cl:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([NH:29][C:16]([C:9]3[CH:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:13][C:12](=[O:14])[NH:11][C:10]=3[CH3:15])=[O:18])[CH:27]=2)[NH:22][N:21]=1

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 160998624-(4-Fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acidHCID 178507360HCID 178507360, compound

Product 1

HCID 178429248HCID 178429248, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 2, Step 2 (170 mg, 0.68 mmol, 1.0 equiv) was combined with 3-chloro-1H-indazol-5-amine (172 mg, 1.02 mmol, 1.5 equiv) and PS-carbodiimide resin (0.994 mmol/g loading, 1.085 g, 1.02 mmol, 1.5 equiv) in 10 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. Purification by flash chromatography (0-50% EtOAc in CH2Cl2) followed by trituration with CH2Cl2 provided 45 mg (16.5%) of the title compound as light pink crystals. MS (ES+) m/e 399 [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. customPurification by flash chromatography (0-50% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-c82b5fa64eec4f9198cf58730559f601
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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