Methanesulfonic Acid → HCID 68867526, compound

HRID 733722Notes

Reaction equation

HRID 733722 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.[CH3:27][O:28][C:29]1[C:30]([NH2:35])=[CH:31][CH:32]=[CH:33][CH:34]=1.CS(O)(=O)=O>O1CCOCC1.CO>[ClH:25].[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH:35][C:13]1[N:14]=[CH:15][C:16]([C:17]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[O:18])=[C:11]2[C:10]([CH3:26])=[CH:9][NH:8][C:12]=12

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 70002-MethoxyanilineHCID 57840771HCID 57840771, compound

Product 1

HCID 68867526HCID 68867526, 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 (120 mg), o-anisidine (71 ul), and methanesulfonic acid (41 μl) in 1,4-dioxane (2 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 (2×10 ml) and water (2×10 ml). The organic layer was dried (MgSO4) and evaporated to give a brown oil. The residue was purified by Biotage chromatography over silica gel (9 g), eluting with hexane followed by 25% ethyl acetate/hexane followed by 50% ethyl acetate/hexane. The residue was dissolved in ethyl acetate (10 ml) and treated with a solution of 1M hydrochloric acid in diethyl ether (10 drops). The resultant solid precipitate was then filtered off, sucked dry then dried at 40° C. under vacuum to afford the title compound (56 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 (2×10 ml) and water (2×10 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customto give a brown oil
  9. customThe residue was purified by Biotage chromatography over silica gel (9 g)
  10. washeluting with hexane
  11. dissolutionThe residue was dissolved in ethyl acetate (10 ml)
  12. additiontreated with a solution of 1M hydrochloric acid in diethyl ether (10 drops)
  13. filtrationThe resultant solid precipitate was then filtered off
  14. customsucked dry
  15. customthen dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-bd2c037ca3a947079d6e529dee210e1f
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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