Triethylamine → Methyl 6-[2-(2-diethylaminomethylazetidin-1-yl)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoate

HRID 2177848Notes

Reaction equation

HRID 2177848 reaction equation
C(N(CC)CC)C.F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([CH2:18][C:19]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([O:29][CH3:30])[C:22]([C:31]2[CH:35]=[CH:34][O:33][CH:32]=2)=[CH:21][CH:20]=1)(=[O:17])=[O:16].Cl.Cl.[CH2:38]([N:40]([CH2:43][CH:44]1[CH2:47][CH2:46][NH:45]1)[CH2:41][CH3:42])[CH3:39]>C(#N)C>[CH2:38]([N:40]([CH2:43][CH:44]1[CH2:47][CH2:46][N:45]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([CH2:18][C:19]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([O:29][CH3:30])[C:22]([C:31]2[CH:35]=[CH:34][O:33][CH:32]=2)=[CH:21][CH:20]=1)(=[O:17])=[O:16])[CH2:41][CH3:42])[CH3:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67107606Methyl 6-(2-fluorobenzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate2×HCID 671079422-Diethylaminomethylazetidine dihydrochloride2×

Product 1

HCID 67107568Methyl 6-[2-(2-diethylaminomethylazetidin-1-yl)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoateYield 59.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

Triethylamine (0.762 ml) was added to a solution of methyl 6-(2-fluorobenzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate (Intermediate 96, 0.0657 g) and 2-Diethylaminomethylazetidine dihydrochloride (Intermediate 206, 0.314 g) in acetonitrile (10 ml) and the mixture was sealed in a microwave vial and heated in the microwave for 3 hours at 140° C. The mixture was cooled to room temperature and evaporated to dryness. DCM and water were added to the residue and the pH was adjusted to 6 by addition of 1M HCl. The organic layer was separated, washed with water, dried (Na2SO4) 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:water (350:20:3:2) to give methyl 6-[2-(2-diethylaminomethylazetidin-1-yl)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoate (0.051 g) as a brown gum.

Workup

  1. customthe mixture was sealed in a microwave vial
  2. temperatureThe mixture was cooled to room temperature
  3. customevaporated to dryness
  4. additionDCM and water were added to the residue
  5. additionthe pH was adjusted to 6 by addition of 1M HCl
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customthe residue was purified by chromatography on silica
  12. washeluting with a mixture of DCM: methanol: acetic acid:water (350:20:3:2)

Sources & evidence

ORD record
ord-14d3c3e883c840ec87fae69059f25b35
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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