Hydrochloric Acid → Methyl 6-[2-(3-diethylaminopropylamino)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoate

HRID 2177838Notes

Reaction equation

HRID 2177838 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH2:11][C:12]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([O:22][CH3:23])[C:15]([C:24]2[CH:28]=[CH:27][O:26][CH:25]=2)=[CH:14][CH:13]=1)(=[O:10])=[O:9].[CH2:29]([N:31]([CH2:36][CH3:37])[CH2:32][CH2:33][CH2:34][NH2:35])[CH3:30].Cl.C(=O)([O-])O.[Na+]>C(#N)C.C(N(CC)CC)C.C(Cl)Cl>[CH2:29]([N:31]([CH2:36][CH3:37])[CH2:32][CH2:33][CH2:34][NH:35][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH2:11][C:12]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([O:22][CH3:23])[C:15]([C:24]2[CH:28]=[CH:27][O:26][CH:25]=2)=[CH:14][CH:13]=1)(=[O:10])=[O:9])[CH3:30]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 61011N,N-Diethyl-1,3-propanediamineHCID 516892Sodium BicarbonateHCID 67107606Methyl 6-(2-fluorobenzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate2×

Product 1

HCID 67107645Methyl 6-[2-(3-diethylaminopropylamino)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoateYield 93.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
130 °C

Procedure

A solution of methyl 6-(2-fluorobenzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate (Intermediate 96, 0.07 g) in acetonitrile (2.2 ml) was added to a solution of N,N-diethyl-1,3-propanediamine (0.225 g) in triethylamine (0.07 g) in a microwave vial. The mixture was heated in the microwave at 130° C. for 2 hours. After cooling, DCM and hydrochloric acid (1M) were added and the pH was adjusted to 8 by addition of saturated aqueous sodium hydrogen carbonate. The mixture was extracted with DCM, washed with brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM, methanol, acetic acid and water (350:20:3:2) to give methyl 6-[2-(3-diethylaminopropylamino)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoate (0.083 g) as a colourless oil.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with DCM
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of DCM, methanol, acetic acid and water (350:20:3:2)

Sources & evidence

ORD record
ord-52f2999ba0d34835bc1897b1d794a736
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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