HCID 13772790, compound → HCID 21796341, compound

HRID 868063Notes

Reaction equation

HRID 868063 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:27])[C:15]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][N:17]3[CH2:20][CH3:21])=[CH:12][C:11]=2[F:28])[S:8][CH:9]=1)=[N+]=[N-].[H][H]>C(O)(=O)C.[Pd]>[NH2:1][CH2:4][C:5]1[N:6]=[C:7]([C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:27])[C:15]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][N:17]3[CH2:20][CH3:21])=[CH:12][C:11]=2[F:28])[S:8][CH:9]=1

Participants

5

Reactant 2

HCID 13772790HCID 13772790, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21796341HCID 21796341, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 0.87 g (2.17 mmol) ethyl 7-[4-(azidomethyl)-2-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 125 ml acetic acid was stirred with 0.10 g 10% palladium on carbon catalyst and hydrogen gas bubbled through for 1.5 hours. After filtration, evaporation of solvent and trituration with ether gave 0.77 g of ethyl 7-[4-(aminomethyl)-2-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate.

Workup

  1. custombubbled through for 1.5 hours
  2. filtrationAfter filtration, evaporation of solvent and trituration with ether

Sources & evidence

ORD record
ord-c891a821133b4c9d9e621bea2b813534
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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