Methanesulfonic Acid → 7-(3-Chloro-phenylamino)-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide

HRID 733680Notes

Reaction equation

HRID 733680 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:12]3[CH:20]=[CH:19][NH:18][C:13]=3[C:14](Cl)=[N:15][CH:16]=2)=[O:10])[CH2:3][CH2:2]1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].CS(O)(=O)=O>O1CCOCC1.CO>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:12]3[CH:20]=[CH:19][NH:18][C:13]=3[C:14]([NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[C:22]([Cl:21])[CH:23]=3)=[N:15][CH:16]=2)=[O:10])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 79323-ChloroanilineHCID 57840793HCID 57840793, compound

Product 1

HCID 578408167-(3-Chloro-phenylamino)-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 7-chloro-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide (20 mg), 3-chloroaniline (15 ul), and methanesulfonic acid (9 ul) in 1,4-dioxane (0.5 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 partitioned between ethyl acetate and 5% sodium hydrogen carbonate solution whereby the title compound remained as a solid at the interface. The solid was filtered off, and washed with 5% sodium hydrogen carbonate solution, water and diethyl ether, then sucked dry and dried at 60° C. under vacuum to afford the title compound (17 mg).

Workup

  1. customThe solid mass obtained
  2. customtransferred to a round bottom flask
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and 5% sodium hydrogen carbonate solution whereby the title compound
  5. filtrationThe solid was filtered off
  6. washwashed with 5% sodium hydrogen carbonate solution, water and diethyl ether
  7. customsucked dry
  8. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-9f991311697d44acbebfd627947ff3ec
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

Loading…