Methanesulfonic Acid → HCID 68867325, compound

HRID 733669Notes

Reaction equation

HRID 733669 reaction equation
C(OC([N:8]1[C:12]2=[C:13]([Cl:25])[N:14]=[CH:15][C:16]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])=[C:11]2[C:10]([CH3:26])=[CH:9]1)=O)(C)(C)C.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.CS(O)(=O)=O>O1CCOCC1.CO>[ClH:25].[CH3:26][C:10]1[C:11]2[C:12](=[C:13]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:14]=[CH:15][C:16]=2[C:17]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[O:18])[NH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8083MorpholineHCID 57840771HCID 57840771, compound

Product 1

HCID 68867325HCID 68867325, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 7-chloro-3-methyl-4-(1-morpholin-4-yl-methanoyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (70 mg), morpholine (64 μl), and methanesulfonic acid (48 μl) in 1,4-dioxane (1 ml) was heated under microwave conditions at 180° C. for 30 minutes. The solid mass obtained was dissolved in methanol, transferred to a round bottom flask and evaporated. The residue was dissolved in dichloromethane (40 ml) and washed with 5% sodium hydrogen carbonate solution (4 ml). The organic layer was dried (MgSO4) and evaporated to give a pale brown foam. The residue was purified by Biotage chromatography over silica gel (50 g), eluting with 2% methanol/dichloromethane followed by 5% methanol/dichloromethane. The residue was dissolved in dichloromethane and treated with a solution of 1M hydrochloric acid in diethyl ether (10 drops). The solution was evaporated and triturated with diethyl ether and the resultant solid was then filtered off, sucked dry then dried at 40° C. under vacuum to afford the title compound (36 mg).

Workup

  1. customThe solid mass obtained
  2. customtransferred to a round bottom flask
  3. customevaporated
  4. dissolutionThe residue was dissolved in dichloromethane (40 ml)
  5. washwashed with 5% sodium hydrogen carbonate solution (4 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customto give a pale brown foam
  9. customThe residue was purified by Biotage chromatography over silica gel (50 g)
  10. washeluting with 2% methanol/dichloromethane
  11. dissolutionThe residue was dissolved in dichloromethane
  12. additiontreated with a solution of 1M hydrochloric acid in diethyl ether (10 drops)
  13. customThe solution was evaporated
  14. customtriturated with diethyl ether
  15. filtrationthe resultant solid was then filtered off
  16. customsucked dry
  17. customthen dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-10e9bfe4fbf3415cbca4ef47fc5e8616
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

Loading…