Methanesulfonic Acid → HCID 68867276, compound

HRID 733665Notes

Reaction equation

HRID 733665 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.[Br:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31].CS(O)(=O)=O>O1CCOCC1.CO>[ClH:25].[Br:27][C:28]1[CH:29]=[C:30]([NH:31][C:13]2[N:14]=[CH:15][C:16]([C:17]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[O:18])=[C:11]3[C:10]([CH3:26])=[CH:9][NH:8][C:12]=23)[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 115623-BromoanilineHCID 57840771HCID 57840771, compound

Product 1

HCID 68867276HCID 68867276, 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, 3-bromoaniline (56 μl), and methanesulfonic acid (33 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 ethyl acetate and washed with 5% sodium hydrogen carbonate solution and water. The organic layer was dried (MgSO4) and evaporated to give an off-white solid. The solid was triturated with diethyl ether, filtered off and sucked dry. The solid was then dissolved in warm 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 (58 mg).

Workup

  1. customThe solid mass obtained
  2. customtransferred to a round bottom flask
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 5% sodium hydrogen carbonate solution and water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customto give an off-white solid
  9. customThe solid was triturated with diethyl ether
  10. filtrationfiltered off
  11. customsucked dry
  12. dissolutionThe solid was then dissolved in warm ethyl acetate (10 ml)
  13. additiontreated with a solution of 1M hydrochloric acid in diethyl ether (10 drops)
  14. filtrationThe resultant solid precipitate was then filtered off
  15. customsucked dry
  16. customthen dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-8128d167f3f04bfa92f9097847838a21
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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