Hydrochloric Acid → HCID 58094765, compound

HRID 1530094Notes

Reaction equation

HRID 1530094 reaction equation
[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21](=S)[NH2:22])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[C:5]2[S:6][CH:7]=[CH:8][N:4]2[N:3]=1.IC.CO[CH:28](OC)[CH2:29][NH2:30].Cl.C(=O)(O)[O-].[Na+]>CC(C)=O.CCOC(C)=O>[NH:30]1[CH:29]=[CH:28][N:22]=[C:21]1[C:12]1[S:11][C:10]([C:9]2[C:2]([CH3:1])=[N:3][N:4]3[CH:8]=[CH:7][S:6][C:5]=23)=[N:14][C:13]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516892Sodium BicarbonateHCID 86649610HCID 86649610, compound

Product 1

HCID 58094765HCID 58094765, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)-4-phenyl-1,3-thiazole-5-carbothioamide (223 mg, 0.6 mmol) obtained in the similar manner described in Example 111-B(ii) in acetone (12 mL), was added iodomethane (75 μL, 1.2 mmol), and the mixture was stirred at rt for 2 h. The solvent was evaporated, and the residue was suspended in AcOH (12 mL). To the residue was added aminoacetaldehyde dimethylacetal (100 μL, 0.9 mmol), and the mixture was stirred at 90° C. for 16 h. The reaction mixture was allowed to cool to rt, then concentrated, and the residue was dissolved in THF (12 mL). To the solution was added 6N hydrochloric acid (400 μL, 2.4 mmol), and the mixture was stirred at 70° C. for 2 h. The reaction mixture was allowed to cool to rt, and then were added saturated aqueous solution of sodium bicarbonate (50 mL) and EtOAc (50 mL). The aqueous layer was extracted with EtOAc (50 mL), and the organic layer was dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/hexane=20/80→100/0) to give the title compound (133 mg, 61%) as a yellow solid.

Workup

  1. customobtained in the similar manner
  2. customThe solvent was evaporated
  3. stirringthe mixture was stirred at 90° C. for 16 h
  4. temperatureto cool to rt
  5. concentrationconcentrated
  6. dissolutionthe residue was dissolved in THF (12 mL)
  7. stirringthe mixture was stirred at 70° C. for 2 h
  8. temperatureto cool to rt
  9. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  10. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  11. customInsoluble materials were removed by filtration
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=20/80→100/0)

Sources & evidence

ORD record
ord-7a0abb1ea4494017980baaf57796af85
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

Loading…