Cesium carbonate → HCID 90280686, compound

HRID 571975Notes

Reaction equation

HRID 571975 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6][CH2:7][C:8](=[O:12])[NH:9][C:10]=2[N:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:19](Cl)[C:20]1[CH:27]=[CH:26][C:23]([O:24][CH3:25])=[CH:22][CH:21]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6][CH2:7][C:8](=[O:12])[N:9]([CH2:19][C:20]3[CH:27]=[CH:26][C:23]([O:24][CH3:25])=[CH:22][CH:21]=3)[C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 59635319HCID 59635319, compound

Product 1

HCID 90280686HCID 90280686, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-chloro-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one (prepared as described in WO 2010/041194, 0.8 g, 3.99 mmol), Cs2CO3 (1.56 g, 4.78 mmol) and PMB-Cl (0.61 mL, 4.39 mmol) in DMF (8 mL) was stirred at rt for 4 h. The solvent was evaporated to dryness and the residue was partitioned between EA (20 mL) and water (25 mL). The aq. layer was extracted once with EA (15 mL) and the combined org. layers were washed with brine (20 mL), dried over Na2SO4 and concentrated to dryness. The residue (1.39 g) was crystallized in a mixture of ether/Hept (2:3). After filtration, the title compound was obtained as an orange solid (1.2 g, 93% yield).

Workup

  1. customThe solvent was evaporated to dryness
  2. customthe residue was partitioned between EA (20 mL) and water (25 mL)
  3. extractionThe aq. layer was extracted once with EA (15 mL)
  4. washlayers were washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue (1.39 g) was crystallized in a mixture of ether/Hept (2:3)
  8. filtrationAfter filtration

Sources & evidence

ORD record
ord-b489ef9674ce448db03133899121c2ec
Source dataset
uspto-grants-2015_05
Patent number
US09029368B2

Reaction notes

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