Water → HCID 86649010, compound

HRID 518094Notes

Reaction equation

HRID 518094 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9]([N:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[CH2:18][O:19][CH3:20])[N:8]=1.O.CN([CH:25]=[O:26])C>>[Cl:6][C:7]1[C:12]([CH:25]=[O:26])=[N:11][CH:10]=[C:9]([N:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[CH2:18][O:19][CH3:20])[N:8]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 866490092-Chloro-6-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine

Product 1

HCID 86649010HCID 86649010, compoundYield 64%

Procedure

Phosphoryl chloride (1.2 mL) was added dropwise to DMF (10 mL) at 0° C., and the mixture was stirred for 20 min. To the reaction mixture was added a solution of 2-chloro-6-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine (1.45 g) in DMF (3 mL), and the mixture was stirred at 50° C. for 16 hr. Water was added to the reaction mixture, and the mixture was stirred for 2 hr, and extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient: 5→50% ethyl acetate/hexane) to give the title compound (1.04 g, 64%).

Workup

  1. stirringthe mixture was stirred at 50° C. for 16 hr
  2. stirringthe mixture was stirred for 2 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent gradient: 5→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f650a64aefbf41f6aaee5473f1e96573
Source dataset
uspto-grants-2015_08
Patent number
US09115139B2

Reaction notes

Loading…