Hydrochloric Acid → HCID 59674002, compound

HRID 1891045Notes

Reaction equation

HRID 1891045 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([CH3:14])(=[N:10][N+:11]([O-:13])=[O:12])=[O:9])[CH:5]=[CH:6][CH:7]=1.[Br:15][C:16]1[C:17]([NH:23][C@H:24]([CH3:27])[CH2:25][OH:26])=[N:18][C:19](Cl)=[N:20][CH:21]=1.Cl.C([O-])(O)=O.[Na+]>C(#N)C.O1CCOCC1>[Br:15][C:16]1[C:17]([NH:23][C@H:24]([CH3:27])[CH2:25][OH:26])=[N:18][C:19]([NH:1][C:2]2[CH:3]=[C:4]([S:8]([CH3:14])(=[N:10][N+:11]([O-:13])=[O:12])=[O:9])[CH:5]=[CH:6][CH:7]=2)=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 58890883HCID 58890883, compound2×HCID 59674008HCID 59674008, compound

Product 1

HCID 59674002HCID 59674002, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 37 mg (0.17 mmol) of (RS)—S-(3-aminophenyl)-S-methyl-N-nitrosulfoximide in 3 ml of acetonitrile is mixed with 91 mg (0.34 mmol) of (R)-2-[(5-bromo-2-chloropyrimidin-4-yl)amino]propan-1-ol and 0.06 ml of a 4 molar solution of hydrochloric acid in dioxane, and it is stirred under reflux overnight. Another 0.05 ml of the 4 molar solution of hydrochloric acid in dioxane is added, and it is refluxed for another 6 hours. After TLC monitoring, it is mixed again with 92 mg (0.34 mmol) of (R)-2-[(5-bromo-2-chloropyrimidin-4-yl)amino]propan-1-ol and refluxed overnight. After cooling, the batch is made basic with saturated NaHCO3 solution and extracted from ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The residue that is obtained is purified by chromatography (DCM/EtOH 95:5). 24 mg (0.05 mmol, corresponding to 32% of theory) of the product is obtained (diastereomers A/B 1:1).

Workup

  1. temperatureunder reflux overnight
  2. temperatureit is refluxed for another 6 hours
  3. temperaturerefluxed overnight
  4. temperatureAfter cooling
  5. extractionextracted from ethyl acetate
  6. dry with materialThe combined organic phases are dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue that is obtained
  10. customis purified by chromatography (DCM/EtOH 95:5)
  11. custom24 mg (0.05 mmol, corresponding to 32% of theory) of the product is obtained (diastereomers A/B 1:1)

Sources & evidence

ORD record
ord-4b4cab32b9a0439384f029da5a287b39
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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