Triethylamine → HCID 10892841, compound

HRID 1597191Notes

Reaction equation

HRID 1597191 reaction equation
[CH3:1][O:2][C@@H:3]([C:5]1[N:10]=[C:9](CS([O-])(=O)=O)[CH:8]=[CH:7][N:6]=1)[CH3:4].[CH3:16][N:17]([CH3:27])[S:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:20])=[O:19].C(N(CC)CC)C>O1CCCC1>[CH3:16][N:17]([CH3:27])[S:18]([N:21]1[CH2:26][CH2:25][N:24]([C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C@H:3]([O:2][CH3:1])[CH3:4])[N:10]=2)[CH2:23][CH2:22]1)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1094966N,N-dimethylpiperazine-1-sulfonamideHCID 86757428HCID 86757428, compound

Product 1

HCID 10892841HCID 10892841, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-(1-methoxyethyl)-pyrimidin-4-yl-methanesulfonate (prepared according to the method of Example 1, Step E, 2.11 g, 9.1 mmol) in tetrahydrofuran (20 mL) was added dimethylsulfamoyl piperazine (prepared according to the method disclosed in U.S. Pat. No. 2,748,129, 1.94 g, 10 mmol) followed by triethylamine (1.4 mL, 10 mmol). The reaction was refluxed for 15 h, and evaporated to an oily residue. This was extracted with ethyl acetate (20 mL) and the extract was washed first with a saturated aqueous solution of sodium bicarbonate and then with water (10 mL). The ethyl acetate extract was dried over sodium sulfate, filtered, and the filtrate was evaporated to a crude product, which was chromatographed over silica gel. Elution with a mixture of 9:1 ethyl acetate and methanol and evaporation of the solvents gave the title compound of Example 1, Step F (1.75 g, 59%); mp, 65-70° C., [α]D+54.4° (c=1, methanol); 1H NMR (CDCl3, 300 MHz) δ1.48(d, 3H), 2.89(s,6H, 3.31(m, 4H), 3.37 (s, 3H), 3.78(m, 4H), 4.34(q, 1H), 6.41(d, 1H), 8.30(d, 1H).

Workup

  1. customprepared
  2. temperatureThe reaction was refluxed for 15 h
  3. customevaporated to an oily residue
  4. extractionThis was extracted with ethyl acetate (20 mL)
  5. washthe extract was washed first with a saturated aqueous solution of sodium bicarbonate
  6. extractionThe ethyl acetate extract
  7. dry with materialwas dried over sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate was evaporated to a crude product, which
  10. customwas chromatographed over silica gel
  11. washElution
  12. additionwith a mixture of 9:1 ethyl acetate and methanol and evaporation of the solvents

Sources & evidence

ORD record
ord-9b91963a5fef4fbb89d01db8da409513
Source dataset
uspto-grants-2001_09
Patent number
US06294538B1

Reaction notes

Loading…