N,N-Dimethylglycine → HCID 178483965, compound

HRID 2290000Notes

Reaction equation

HRID 2290000 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][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]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.[CH3:40][N:41]([CH3:46])[CH2:42][C:43](O)=[O:44]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:40][N:41]([CH3:46])[CH2:42][C:43]([O:24][CH2:23][CH2:22][CH2:21][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([F:25])[CH:15]=1)[N:12]=[CH:11][C:10]([C:8]([NH:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][CH:26]=1)=[O:9])=[C:19]2[OH:20])=[O:44]

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178522910HCID 178522910, compound

Product 1

HCID 178483965HCID 178483965, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-quinolinecarboxamide from Example No. 110 (0.23 g), EDC hydrochloride (0.22 g), and DMAP (0.022 g) in 7 mL pyridine is added N,N-dimethylglycine (0.12 g). The reaction is allowed to stir at room temperature overnight. The solvent is removed in vacuo and the residue partitioned between CH2Cl2 and water. The organic layer is washed once with water, once with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is adsorbed onto silica and purified by chromatography on a Biotage Flash 40S column (eluent 1.5% MeOH:CH2Cl2 (1 L), 2.5% MeOH:CH2Cl2 (1 L), and 4% MeOH:CH2Cl2 (1 L)). The product-containing fractions are concentrated in vacuo to give a white solid which is further triturated in EtOH, filtered, washed with hexanes, and dried. (0.14 g, 51%).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue partitioned between CH2Cl2 and water
  3. washThe organic layer is washed once with water, once with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography on a Biotage Flash 40S column (eluent 1.5% MeOH:CH2Cl2 (1 L), 2.5% MeOH:CH2Cl2 (1 L), and 4% MeOH:CH2Cl2 (1 L))
  8. concentrationThe product-containing fractions are concentrated in vacuo
  9. customto give a white solid which
  10. customis further triturated in EtOH
  11. filtrationfiltered
  12. washwashed with hexanes
  13. customdried

Sources & evidence

ORD record
ord-78f3f8e922584a808ba53285296fbcff
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…