Triethylamine → HCID 22873793, compound

HRID 1683873Notes

Reaction equation

HRID 1683873 reaction equation
Cl.[CH2:2]([S:4]([CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][C@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1)(=[O:6])=[O:5])[CH3:3].[CH:24]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH2:25].C(N(CC)CC)C>CN(C)C(=O)C>[CH2:2]([S:4]([CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:25][CH2:24][S:26]([CH3:29])(=[O:28])=[O:27])(=[O:6])=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19354Methyl vinyl sulfoneHCID 22873789HCID 22873789, compound

Product 1

HCID 22873793HCID 22873793, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

5-(2-Ethylsulphonylethyl)-3-(2(R)-pyrrolidinylmethyl)-1H-indole hydrochloride (Preparation 5; 200 mg, 0.56 mmol) was dissolved in N,N-dimethylacetamide (4 ml) under nitrogen at room temperature, then methyl vinyl sulphone (0.06 ml, 0.69 mmol) and triethylamine (0.2 ml) were added. The resulting mixture was heated at 100° C. for 18 hours, allowed to cool, then partitioned between ethyl acetate and water. The organic phase was separated, washed with water, dried (Na2SO4) and evaporated under reduced pressure. The resulting crude material was purified by column chromatography on silica gel, eluting with a gradient of ethanol in dichloromethane (0 to 5% ethanol), to afford the title compound as a gum (130 mg). Rf 0.70 (SS 4). [α]D25 +43° (c=0.1, CH3OH). Found: C,55.38; H,7.12; N,6.50. C20H30N2O4S2 ; 0.10 CH2Cl2 requires C,55.48; H,7.00; N,6.44%. δ(CDCl3): 1.38(3H,t), 1.50-1.90(5H,m), 2.22(1H,m), 2.60-2.80(3H,m), 2.90-3.35(12H,m), 3.48(1H,m), 5.30(0.20H,s,CH2Cl2), 6.98-7.10(2H,m), 7.30(1H,d), 7.44(1H,s), 8.22(1H,br s).

Workup

  1. temperatureto cool
  2. custompartitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe resulting crude material was purified by column chromatography on silica gel
  8. washeluting with a gradient of ethanol in dichloromethane (0 to 5% ethanol)

Sources & evidence

ORD record
ord-3a655e3d3fa94110b47e1a2a780d01e9
Source dataset
uspto-grants-1997_06
Patent number
US05639779

Reaction notes

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