4-METHYL-N-(3-OXO-3-(PYRROLIDIN-1-YL)PROPYL)BENZENESULFONAMIDE synthesis

6synthesis methods

Product Name:4-METHYL-N-(3-OXO-3-(PYRROLIDIN-1-YL)PROPYL)BENZENESULFONAMIDE
CAS Number:122081-15-6
Molecular formula:C14H20N2O3S
Molecular Weight:296.39

123-75-1 Synthesis

123-75-1
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Propanoyl chloride, 3-[[(4-methylphenyl)sulfonyl]amino]-

61341-03-5
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4-METHYL-N-(3-OXO-3-(PYRROLIDIN-1-YL)PROPYL)BENZENESULFONAMIDE

122081-15-6
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Yield:122081-15-6 97 g

Reaction Conditions:

in dichloromethane at 20; for 2 h;

Steps:

1 Synthesis of 3-{[(4-methylphenyl)sulfonyl]amino}-1-pyrrolidinylpropan-1-one (3)

To a solution of (2) (90.0 g, 0.37 mol) in SOCl2 (900 mL), stirred with refluxing for 2.5 h, then concentrated and residue was dissolved in DCM was added pyrrolidine (71.1 g, 0,99 mol) in DCM, then stirred at room temperature for 2 h. The reaction mixture was diluted with water and extracted with DCM (100 mL x 3), washed with brine, dried over Na₂SO₄and filtered, the filtrate was evaporated to remove the solvent. The residue was purified by on silica gel (DCM/MeOH = 80/1) to give compound 3 (97 g, 88%) as white solid. ¹H NMR (400 MHz, DMSO-d₆); δ 1.83-1.88 (m, 2H), 1.91 - 1.96 (m, 2H), 2,42 (s, 3H), 2.43-2,49 (t, 2H), 3.17-3.2 (m, 2H), 3.28-3.31 (t, 2H), 3.40-3.43 (t, 2H), 5.67-5,70 (t, 2H), 7.29-7,31 (d, J = 8 Hz, 2H), 7.74-7,62 (d, J = 8 Hz, 2H); MS Calcd,: 296; MS Found: 297 ([M+H]⁺).

References:

WO2015/38661,2015,A1 Location in patent:Paragraph 0137

98-59-9 Synthesis

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References

3-(TOLUENE-4-SULFONYLAMINO)-PROPIONIC ACID

42908-33-8
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References

98-09-9
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References

31867-78-4
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References