Potassium bisulfate → HCID 22049996, compound

HRID 1832070Notes

Reaction equation

HRID 1832070 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][N:15]=2)[C:8](=[O:24])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])(O)(=O)=O.[K+]>O1CCCC1>[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([CH2:18][OH:19])=[CH:16][N:15]=2)[C:8](=[O:24])[CH:7]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 22049922HCID 22049922, compound

Product 1

HCID 22049996HCID 22049996, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 6-{[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]methyl}nicotinate (from preparation of step 3) (350 mg, 0.87 mmol) was added into anhydrous tetrahydrofuran (15 ml) and the solution was cooled to −78° C. Into the cold solution, was added lithium aluminum hydride (100 mg, 2.6 mmol). After the addition, the reaction mixture was warm to 0 C and continue stirring for one additional hour. Potassium hydrogen sulfate (1 N solution, 150 ml) was added slowly into the reaction mixture to quench the reaction. The resulting mixture was transferred to a separatory funnel and the product was extracted with ethyl acetate (200 ml×2). The combine ethyl acetate solution was dried over anhydrous magnesium sulfate and evaporated to dryness. LC/MS, tr=1.88 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-MS m/z 373 (M+H)

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was warm to 0 C
  3. customto quench
  4. customthe reaction
  5. customThe resulting mixture was transferred to a separatory funnel
  6. extractionthe product was extracted with ethyl acetate (200 ml×2)
  7. dry with materialThe combine ethyl acetate solution was dried over anhydrous magnesium sulfate
  8. customevaporated to dryness
  9. customLC/MS, tr=1.88 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50° C.)

Sources & evidence

ORD record
ord-ab40307a74104246aa38a80dd534ddca
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

Loading…