Sodium Carbonate → HCID 10020676, compound

HRID 1063102Notes

Reaction equation

HRID 1063102 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7](N3CCNCC3)=[CH:8][C:9]=2[CH2:11][CH2:12][CH3:13])[S:4][C:3]=1[C:20]([NH2:22])=[O:21].[CH3:23][N:24]1[CH2:30][CH2:29][CH2:28][C@H:25]1[CH2:26][OH:27].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:27][CH2:26][CH:25]3[CH2:28][CH2:29][CH2:30][N:24]3[CH3:23])=[CH:8][C:9]=2[CH2:11][CH2:12][CH3:13])[S:4][C:3]=1[C:20]([NH2:22])=[O:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 11723489HCID 11723489, compound

Product 1

HCID 10020676HCID 10020676, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture pyridine-triflate intermediate (see Example 1) (10 mg) and N-methyl-L-prolinol (40 mg) in dioxane was heated under Ar at 90° C. for 3 h. The mixture was cooled to room temperature, and Na2CO3 (2 M, 0.2 mL) was added. The mixture was heated at 100° C. under Ar for 10 h, cooled to room temperature and diluted with water (1 mL). The mixture was extracted with EtOAc, dried with Na2SO4 and concentrated. The residue was purified by preparative silica gel chromatography to give 6 mg of the title compound as a white solid.

Workup

  1. temperatureThe mixture was heated at 100° C. under Ar for 10 h
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative silica gel chromatography

Sources & evidence

ORD record
ord-86e85276922b4fbcb9153fabd5a5942e
Source dataset
uspto-grants-2005_11
Patent number
US06964956B2

Reaction notes

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