Methanesulfonic Acid → HCID 57840790, compound

HRID 733659Notes

Reaction equation

HRID 733659 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[CH:14][NH:13][C:8]=2[C:9](Cl)=[N:10][CH:11]=1)=[O:5])C.[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].CS(O)(=O)=O.[OH-].[K+]>O1CCOCC1.C(O)C>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:9]2[C:8]3[NH:13][CH:14]=[C:15]([CH3:16])[C:7]=3[C:6]([C:4]([OH:3])=[O:5])=[CH:11][N:10]=2)[CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 79323-ChloroanilineHCID 14797Potassium HydroxideHCID 57840812HCID 57840812, compound

Product 1

HCID 57840790HCID 57840790, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 7-chloro-3-methyl-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid ethyl ester (180 mg), 3-chloroaniline (160 μl), and methanesulfonic acid (98 μl) in 1,4-dioxane (5 ml) was heated under microwave conditions at 180° C. for 30 minutes. The solid mass obtained was suspended in ethanol (6 ml) and treated with a solution of potassium hydroxide (170 mg) in ethanol (2 ml) and then refluxed overnight. The ethanol was evaporated and replaced with methanol (8 ml) and potassium hydroxide (56 mg) added and then the mixture was refluxed overnight. The mixture was evaporated to dryness and the residue dissolved in water which washed twice with diethyl ether. The aqueous was then acidified with concentrated hydrochloric acid to afford a precipitate. The precipitate was filtered off and washed with water. The solid was then sucked dry and dried to afford the title compound (178 mg).

Workup

  1. customThe solid mass obtained
  2. temperaturerefluxed overnight
  3. customThe ethanol was evaporated
  4. additionadded
  5. temperaturethe mixture was refluxed overnight
  6. customThe mixture was evaporated to dryness
  7. dissolutionthe residue dissolved in water which
  8. washwashed twice with diethyl ether
  9. customto afford a precipitate
  10. filtrationThe precipitate was filtered off
  11. washwashed with water
  12. customThe solid was then sucked dry
  13. customdried

Sources & evidence

ORD record
ord-feac1b0203e14cbfb15bf64af4d3def3
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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