HCID 131730950, compound → HCID 131730952, compound

HRID 2035495Notes

Reaction equation

HRID 2035495 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[N:19]=[CH:18][C:17]([CH2:20][C:21]([NH2:23])=[O:22])=[C:16]([NH:24][CH2:25][C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=3)[CH:15]=2)=[CH:9][CH:8]=1)=[N+]=[N-]>C(O)C.[C].[Pd]>[NH2:1][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[N:19]=[CH:18][C:17]([CH2:20][C:21]([NH2:23])=[O:22])=[C:16]([NH:24][CH2:25][C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=3)[CH:15]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 131730950HCID 131730950, compound2×

Product 1

HCID 131730952HCID 131730952, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

229 mg of 6-{[4-(3-azidopropyl)phenyl]amino}-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 200) was dissolved in 30 mL of ethanol, to which 46 mg of 10% palladium carbon was added, and stirred under a hydrogen atmosphere at room temperature for 1 hour. The 10% palladium carbon was filtered off, the solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol=10:1 to chloroform:ammonia methanol=10:1) to obtain 161 mg (75%) of the title compound as a white crystalline powder.

Workup

  1. additionwas added
  2. filtrationThe 10% palladium carbon was filtered off
  3. customthe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (chloroform:methanol=10:1 to chloroform:ammonia methanol=10:1)

Sources & evidence

ORD record
ord-cfdcb962a0d848d899bc0e4224cf3371
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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