HCID 117667705, compound → HCID 117667361, compound

HRID 712726Notes

Reaction equation

HRID 712726 reaction equation
[N:1]([C@@H:4]([C:6]1[C:11]([F:12])=[CH:10][N:9]=[CH:8][C:7]=1[C:13]1[CH:14]=[C:15]2[C:20](=[N:21][CH:22]=1)[N:19]([C:23]([NH2:25])=[O:24])[CH2:18][CH2:17][CH2:16]2)[CH3:5])=[N+]=[N-]>CCOC(C)=O.CO.[Pd]>[NH2:1][C@@H:4]([C:6]1[C:11]([F:12])=[CH:10][N:9]=[CH:8][C:7]=1[C:13]1[CH:14]=[C:15]2[C:20](=[N:21][CH:22]=1)[N:19]([C:23]([NH2:25])=[O:24])[CH2:18][CH2:17][CH2:16]2)[CH3:5]

Participants

5

Reactant 1

HCID 117667705HCID 117667705, compound

Product 1

HCID 117667361HCID 117667361, compoundYield 34.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-[4-((R)-1-azido-ethyl)-5-fluoro-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (90 mg, 0.24 mmol) is dissolved in a mixture of EtOAc (2 mL) and MeOH (3 mL). The flask is flushed with Argon. Pd/C (26 mg, 0.024 mmol, 10%) is added and the flask is flushed with H2. After stirring for 18 hrs, the reaction is diluted with EtOAc and MeOH (10 mL of a 1:1 mixture), filtered and concentrated. The residue is dissolve in 1 mL of MeOH and 2 drops of water is added. The solution is filtered and purified by reverse phase HPLC to give 26 mg of the titled product.

Workup

  1. customThe flask is flushed with Argon
  2. customthe flask is flushed with H2
  3. additionthe reaction is diluted with EtOAc and MeOH (10 mL of a 1:1 mixture),
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue is dissolve in 1 mL of MeOH
  7. addition2 drops of water is added
  8. filtrationThe solution is filtered
  9. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-397f8903d2eb44faa4d008fc27fdd8b1
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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