Potassium Carbonate → HCID 86643692, compound

HRID 1672752Notes

Reaction equation

HRID 1672752 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15]([C:17]1[C:18]([Cl:26])=[N:19][C:20]([S:24][CH3:25])=[N:21][C:22]=1Cl)=[O:16]>O1CCOCC1>[Cl:26][C:18]1[C:17]2[C:15](=[O:16])[NH:14][CH2:13][C@H:9]3[N:8]([CH2:12][CH2:11][CH2:10]3)[C:22]=2[N:21]=[C:20]([S:24][CH3:25])[N:19]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86643693HCID 86643693, compound

Product 1

HCID 86643692HCID 86643692, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1,4-Dioxane (5.4 mL) and potassium carbonate (770 mg, 5.60 mmol) were added to (S)—N-[(pyrrolidin-2-yl)methyl]-4,6-dichloro-2-methylthiopyrimidine-5-carboxylic acid amide hydrochloride (100 mg, 0.280 mmol) obtained in Reference Example 8, and the mixture was stirred at 80° C. for 2 hours. The mixture was filtered through sellite, and the residue was washed with chloroform. After concentrating the filtrate under reduced pressure, the residue was purified by silica gel column chromatography to give (S)-7-chloro-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (10.6 mg, 13%).

Workup

  1. customobtained in Reference Example 8
  2. filtrationThe mixture was filtered through sellite
  3. washthe residue was washed with chloroform
  4. concentrationAfter concentrating the filtrate under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc263f72db644a25855c8b9a406e3349
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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