Tetrahydrofuran → HCID 178522853, compound

HRID 2290028Notes

Reaction equation

HRID 2290028 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21](O)=[O:22])=[CH:15][C:14]=3[F:24])=[O:9])=[CH:4][CH:3]=1.C1COCC1.S(Cl)(Cl)=O.[Cl:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1>CN(C=O)C.N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]([NH:42][CH2:41][C:40]2[CH:43]=[CH:44][C:37]([Cl:36])=[CH:38][CH:39]=2)=[O:22])=[CH:15][C:14]=3[F:24])=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 660364-ChlorobenzylamineHCID 178524524HCID 178524524, compound

Product 1

HCID 178522853HCID 178522853, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a flask containing 3-{[(4-chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-quinolinecarboxylic acid from Preparation No. 24 (0.11 g) and THF (3 mL) is added thionyl chloride (0.075 mL). The reaction mixture is stirred overnight then treated with one drop of DMF. After 4 hours, the reaction is concentrated under reduced pressure. The residue is triturated with toluene (2×) and dried in vacuo to afford a light yellow solid. The solid is dissolved in pyridine (2 mL), treated with p-chlorobenzylamine (0.04 mL), and a small amount of 4-dimethylaminopyridine is added. After stirring overinght, the reaction is concentrated under reduced pressure. The residue is triturated with toluene (3×) and dried in vacuo. The residue is adsorbed onto silica and chromatographed on silica eluting with 2% MeOH:CH2Cl2 to 6% MeOH:CH2Cl2. The product-containing fractions are evaporated to give a solid which is crystallized from methanol:toluene to afford 0.04 g of the title compound.

Workup

  1. customfrom Preparation No
  2. waitAfter 4 hours
  3. concentrationthe reaction is concentrated under reduced pressure
  4. customThe residue is triturated with toluene (2×)
  5. customdried in vacuo
  6. customto afford a light yellow solid
  7. stirringAfter stirring overinght
  8. concentrationthe reaction is concentrated under reduced pressure
  9. customThe residue is triturated with toluene (3×)
  10. customdried in vacuo
  11. customchromatographed on silica eluting with 2% MeOH
  12. customThe product-containing fractions are evaporated
  13. customto give a solid which
  14. customis crystallized from methanol

Sources & evidence

ORD record
ord-099d25d385454eeaa4de164c65311c1c
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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