Carbodiimide → HCID 178429241, compound

HRID 734674Notes

Reaction equation

HRID 734674 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17](O)=[O:18])=[CH:5][CH:4]=1.[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:17]([C:10]3[CH:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:20])([F:21])[F:1])=[CH:8][CH:7]=4)[CH2:14][C:13](=[O:15])[NH:12][C:11]=3[CH3:16])=[O:18])[CH:30]=2)[NH:25][N:24]=1

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acidHCID 178507360HCID 178507360, compound

Product 1

HCID 178429241HCID 178429241, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 5, Step 2 (0.100 g, 0.330 mmol, 1.00 equiv), 3-chloro-1H-indazol-5-amine (84 mg, 0.502 mmol, 1.50 equiv) and PS-carbodiimide resin (456 mg, 0.502 mmol, 1.00 equiv) were suspended in 2.0 mL DMF and stirred overnight at room temperature. The reaction mixture was concentrated to approximately 1 mL DMF and water was added. The resulting precipitate was collected by filtration and washed with 50% CH2Cl2/hexanes. The product was purified by preparative reverse phase HPLC (19×50 Xterra Prep RP 10-90% CH3CN/5 mM NH4HCO3 over 9 min, 25 ml/min) to provide 5.0 mg (3%) of the title compound as a white solid. MS (ES+) m/e 449 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated to approximately 1 mL DMF and water
  2. additionwas added
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with 50% CH2Cl2/hexanes
  5. customThe product was purified by preparative reverse phase HPLC (19×50 Xterra Prep RP 10-90% CH3CN/5 mM NH4HCO3 over 9 min, 25 ml/min)

Sources & evidence

ORD record
ord-a0433b34417a487baeeaa05f0ec0f0a1
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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