Hydrochloric Acid → HCID 68868166, compound

HRID 733756Notes

Reaction equation

HRID 733756 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:12])[N:10]([CH3:11])[C:6]=2[C:5]([C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])=[CH:4][N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].CS(O)(=O)=O.Cl>O1CCOCC1.C(OCC)(=O)C.C(OCC)C>[ClH:1].[Cl:21][C:22]1[CH:23]=[C:24]([NH:25][C:2]2[C:7]3[CH:8]=[C:9]([CH3:12])[N:10]([CH3:11])[C:6]=3[C:5]([C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:14])=[CH:4][N:3]=2)[CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 79323-ChloroanilineHCID 57840986HCID 57840986, compound

Product 1

HCID 68868166HCID 68868166, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-chloro-1,2-dimethyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine (68 mg), 3-chloroaniline (0.05 ml) and methanesulfonic acid (0.03 ml) in dry 1,4-dioxan was heated under microwave conditions at 180° C. for fifteen minutes. The reaction mixture was transferred to a round bottom flask and evaporated. The residue was partitioned between ethyl acetate (10 ml) and saturated sodium bicarbonate solution and washed with saturated sodium bicarbonate solution and water. The organic layer was dried (MgSO4) and evaporated to afford a brown oil. The oil was purified by Biotage chromatography on silica gel loading the column using dichloromethane and eluting with 5% ethyl acetate/hexane (200 ml) increasing the percentage of ethyl acetate to 20%, 50% and 100% to afford a white foam. The foam was dissolved in warm ethyl acetate and treated with 1M hydrochloric acid in diethyl ether. The mixture was evaporated, the residue triturated with diethyl ether to afford a white solid which was filtered off, washed with diethyl ether and dried to afford the title compound (59 mg).

Workup

  1. customThe reaction mixture was transferred to a round bottom flask
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate (10 ml) and saturated sodium bicarbonate solution
  4. washwashed with saturated sodium bicarbonate solution and water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customto afford a brown oil
  8. customThe oil was purified by Biotage chromatography on silica gel loading the column
  9. washeluting with 5% ethyl acetate/hexane (200 ml)
  10. temperatureincreasing the percentage of ethyl acetate to 20%, 50% and 100%
  11. customto afford a white foam
  12. customThe mixture was evaporated
  13. customthe residue triturated with diethyl ether
  14. customto afford a white solid which
  15. filtrationwas filtered off
  16. washwashed with diethyl ether
  17. customdried

Sources & evidence

ORD record
ord-4a43bfa002264524bf14eac968bb03e9
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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