Sodium Sulfate → HCID 10195805, compound

HRID 970377Notes

Reaction equation

HRID 970377 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]([OH:22])[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[C:4](=[O:23])[CH2:3]1.[O:24]=[C:25]1[NH:30][C:29]2[CH:31]=[C:32]([CH:35]=O)[CH:33]=[CH:34][C:28]=2[S:27][CH2:26]1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH4-].[Na+]>CN(C=O)C>[OH:22][C@H:9]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1)[CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][CH2:35][C:32]2[CH:33]=[CH:34][C:28]3[S:27][CH2:26][C:25](=[O:24])[NH:30][C:29]=3[CH:31]=2)[CH2:3][C:4]1=[O:23]

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 109433483-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehydeHCID 58699957HCID 58699957, compound

Product 1

HCID 10195805HCID 10195805, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-1-[(R)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-2-one (4e) (1 equiv.), 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbaldehyde (in) (1.1 equiv.), and Na2SO4 in DMF is stirred until the imine has formed, then is filtered through a sintered glass funnel. The filtrate is concentrated to dryness in vacuo, and the residue is dissolved in MeOH. NaBH4 (1 equiv.) is added, and the reaction is stirred until the imine is consumed. The solvent is removed in vacuo and the residue is taken up in dilute HCl. The mixture is neutralized with dilute NaOH and extracted with CH2Cl2. Drying (Na2SO4), concentration, and flash chromatography on silica gel gives the title compound.

Workup

  1. customhas formed
  2. filtrationis filtered through a sintered glass funnel
  3. concentrationThe filtrate is concentrated to dryness in vacuo
  4. dissolutionthe residue is dissolved in MeOH
  5. customis consumed
  6. customThe solvent is removed in vacuo
  7. extractionextracted with CH2Cl2
  8. customDrying
  9. concentration(Na2SO4), concentration, and flash chromatography on silica gel

Sources & evidence

ORD record
ord-af6cb3c5c15c49a3830120c395ea7608
Source dataset
uspto-grants-2007_12
Patent number
US07312212B2

Reaction notes

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