Potassium hydroxy sulfite → HCID 117667332, compound

HRID 712640Notes

Reaction equation

HRID 712640 reaction equation
S1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([C:13]3[CH:14]=[C:15]4[C:20](=[N:21][CH:22]=3)[N:19]([C:23]([NH2:25])=[O:24])[CH2:18][CH2:17][CH2:16]4)[CH:10]=[N:11][CH:12]=2)[CH2:3][CH2:2]1.O[O:27][S:28]([O-:30])=O.[K+]>O1CCOCC1.O>[O:27]=[S:28]1(=[O:30])[CH2:2][CH:3]=[C:4]([C:7]2[CH:8]=[C:9]([C:13]3[CH:14]=[C:15]4[C:20](=[N:21][CH:22]=3)[N:19]([C:23]([NH2:25])=[O:24])[CH2:18][CH2:17][CH2:16]4)[CH:10]=[N:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86305856HCID 86305856, compound

Product 1

HCID 117667332HCID 117667332, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To 6-[5-(3,6-dihydro-2H-thiopyran-4-yl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (57 mg, 0.16 mmol) in 2 mL of 1:1 dioxane/H2O is added oxone (266 mg, 0.32 mmol). The mixture is stirred for 2 h. The mixture is quenched by addition of sodium sulfite and concentrated. The residue is suspended into MeOH and filtered. The filtrate is concentrated and purified via the Preparative HPLC (5%-70% CH3CN/H2O) to give 62.6 mg of the titled product.

Workup

  1. customThe mixture is quenched by addition of sodium sulfite
  2. concentrationconcentrated
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. custompurified via the Preparative HPLC (5%-70% CH3CN/H2O)

Sources & evidence

ORD record
ord-45177530bce245dfadaafc798d274c33
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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