Sodium borohydride → N,N-bis(2-hydroxyethyl)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide

HRID 1166286

Reaction equation

HRID 1166286 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[CH:23][C:22]([C:32]([F:35])([F:34])[F:33])=[N:21]2)=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:6][C:7](OC)=[O:8].[BH4-].[Na+]>CO>[OH:8][CH2:7][CH2:6][N:5]([CH2:4][CH2:3][OH:2])[S:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[CH:23][C:22]([C:32]([F:33])([F:35])[F:34])=[N:21]2)=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 22647645Methyl N-(2-Methoxy-2-oxoethl)-N-({4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}sulfonyl)glycinate

Product 1

HCID 10162229N,N-bis(2-hydroxyethyl)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl N-(2-methoxy-2-oxoethyl)-N-({4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}sulfonyl)glycinate prepared as in example 2.A. (0.330 g, 0.628 mmol) in anhydrous methanol (50 mL), was added NaBH4 (0.4 g, 10.6 mmol) and the mixture was allowed to stand at room temperature for 2 hours. Additional NaBH4 (0.4 g, 10.6 mmol) was then added and after 1 hour, the solvent was removed in vacuo. The residue was dissolved in water (100 mL), saturated with NaCl and the pH was adjusted to 2 with 1N HCl. The solution was extracted with ethyl acetate (200 mL). The organic solution was washed with sat. NaCl (50 mL), dried over MgSO4, filtered and concentrated under vacuum to afford 0.285 g (97% yield) of the product as a white powder: mp, 79.1° C.; 1H NMR (dmso-d6/300 MHz) δ 7.87 (d, 2H, J=8.7 Hz), 7.54 (d, 2H, J=8.7 Hz), 7.23-7.16 (m, 5H), 4.81 (exchangeable with D2O, t, 2H, J=5.4 Hz), 3.52-3.46 (m, 4H), 3.20 (t, 4H, J=6.0 Hz), 2.30 (s, 3H); HRMS (M+H)+ calcd. for C21H23F3N3O4S: 470.1361; found 470.1330.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water (100 mL), saturated with NaCl
  3. extractionThe solution was extracted with ethyl acetate (200 mL)
  4. washThe organic solution was washed with sat. NaCl (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3fa295a02fce4fd19ca9b7d7016d92ee
Source dataset
uspto-grants-2003_09
Patent number
US06613790B2

Linked notes

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