Formaldehyde → 1-(4'-Methylbenzenesulfonyl)-3-hydroxy-4-(pyrrolidin-1-ylmethyl)pyridin-2(1H)-one

HRID 2168184Notes

Reaction equation

HRID 2168184 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:12]2=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:19]=O.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:16]=[CH:15][C:14]([CH2:19][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[C:13]([OH:17])[C:12]2=[O:18])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 112770823-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one

Product 1

HCID 104278401-(4'-Methylbenzenesulfonyl)-3-hydroxy-4-(pyrrolidin-1-ylmethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4′-Methylbenzenesulfonyl)-3-hydroxypyridin-2(1H)-one (7) (250 mg, 0.94 mmol) and formaldehyde (200 mg, 2.07 mmol) are combined in aqueous ethanol (10 mL) and stirred for 30 minutes. Pyrrolidine (149 mg, 2.07 mmol) is then added and the reaction stirred for 12 hours. The solvent is removed by evaporation and the residue dissolved in methanol (5 mL) and purified via prep HPLC eluting with water/acetonitrile to afford the desired product. 1H NMR (300 MHz, DMSO) δ 1.87 (m, 2H), 1.99 (m, 2H), 2.44 (s, 3H), 3.09 (m, 2H), 3.40 (m, 2H), 4.19 (s, 2H), 6.51 (d, J=7.5 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.76 (d, J=7.5 Hz, 1H), 7.98 (d, J=8.1 Hz, 1H), 9.93 (broad s, 1H); 19F NMR (252 MHz, DMSO) δ 88.4; 13C NMR (75 MHz, DMSO) δ 21.5, 22.7, 50.5, 53.7, 108.7, 118.6, 119.4, 128.4, 129.7, 130.1, 133.1, 146.8, 147.7, 156.2; ES MS (M+1) 349.25; HRMS Calcd. For C17H20N2O4S, 348.42. Found (M+1) 349.42.

Workup

  1. stirringthe reaction stirred for 12 hours
  2. customThe solvent is removed by evaporation
  3. dissolutionthe residue dissolved in methanol (5 mL)
  4. custompurified via prep HPLC
  5. washeluting with water/acetonitrile

Sources & evidence

ORD record
ord-e58ddfc62c7c4785aad5d6bc0e6bad2e
Source dataset
uspto-grants-2015_06
Patent number
US09045495B2

Reaction notes

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