Hydrochloric Acid → HCID 68542319, compound

HRID 1992298Notes

Reaction equation

HRID 1992298 reaction equation
[CH3:1][C@@:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:19]=[N:20][CH:21]=[N:22][CH:23]=3)[CH:13]=2)[CH2:7][CH2:6][S:5][C:4]([NH:8]C(=O)C)=[N:3]1.[ClH:24]>>[ClH:24].[ClH:24].[CH3:1][C@@:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:19]=[N:20][CH:21]=[N:22][CH:23]=3)[CH:13]=2)[CH2:7][CH2:6][S:5][C:4]([NH2:8])=[N:3]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68543021HCID 68543021, compound

Product 1

HCID 68542319HCID 68542319, compoundYield 81%

Procedure

A solution of (S)-N-[4-Methyl-4-(3-pyrimidin-5-yl-phenyl)-5,6-dihydro-4H-[1,3]thiazin-2-yl]-acetamide (2.7 g, 8.3 mmoles, 1.0 equiv) is stirred in 5N hydrogen chloride (50 mL, 250 mmoles, 30 equiv) at 100° C. for 2 h. The reaction is cooled and the volatiles are removed under reduced pressure. The resulting residue is dissolved in water and extracted with ethyl acetate. The aqueous phase is neutralized with saturated aqueous sodium bicarbonate and extracted ethyl acetate. The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is filtered through a silica gel plug and washed with ethyl acetate. The silica gel plug is further washed with ethyl acetate containing ethyl acetate and 10% isopropyl amine. The 10% isopropyl amine in ethyl acetate wash is collected and the solvent removed under reduced pressure. The resulting free amine is dissolved in a solution of 100 mL of water containing 14 mL of 1 N HCl. The resulting solution is freeze dried to give the title compound (81% yield): MS (m/z): 285 (M+1).

Workup

  1. temperatureThe reaction is cooled
  2. customthe volatiles are removed under reduced pressure
  3. dissolutionThe resulting residue is dissolved in water
  4. extractionextracted with ethyl acetate
  5. extractionextracted ethyl acetate
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a residue
  10. filtrationThe residue is filtered through a silica gel plug
  11. washwashed with ethyl acetate
  12. washThe silica gel plug is further washed with ethyl acetate
  13. additioncontaining ethyl acetate and 10% isopropyl amine
  14. washThe 10% isopropyl amine in ethyl acetate wash
  15. customis collected
  16. customthe solvent removed under reduced pressure
  17. dissolutionThe resulting free amine is dissolved in a solution of 100 mL of water containing 14 mL of 1 N HCl
  18. customdried

Sources & evidence

ORD record
ord-8625d1dca2df45bb8420472fa4859a60
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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