Morpholine → 2',4'-Difluoro-N-(3-(1-hydroxy-2-morpholinoethyl)phenyl)biphenyl-4-sulfonamide

HRID 221394Notes

Reaction equation

HRID 221394 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]3[CH2:27][O:26]3)[CH:20]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([OH:26])[CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:20]=2)(=[O:16])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 866562622',4'-Difluoro-N-(3-(oxiran-2-yl)phenyl)biphenyl-4-sulfonamide

Product 1

HCID 451381862',4'-Difluoro-N-(3-(1-hydroxy-2-morpholinoethyl)phenyl)biphenyl-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using a method analogous to Method D, using 2′,4′-difluoro-N-(3-(oxiran-2-yl)phenyl)biphenyl-4-sulfonamide and 1 M morpholine in methanol, a mixture of regioisomers was obtained. Reverse-phase HPLC was used to purify the mixture and the title compound was obtained as a pale orange powder. 1H NMR (300 MHz, CDCl3): δ 2.20-2.40 (3H, m), 2.50-2.70 (2H, m), 3.60-3.80 (4H, m), 4.66 (1H, m), 6.85-7.00 (2H, m), 7.03-7.19 (3H, m), 7.20-7.30 (1H, m), 7.30-7.40 (1H, m), 7.57 (2H, d, J=8 Hz) and 7.91 (2H, d, J=8 Hz). MS, m/z: Calcd, 474.142. Found, 474.56 (M).

Workup

  1. additiona mixture of regioisomers
  2. customwas obtained
  3. customto purify the mixture

Sources & evidence

ORD record
ord-a5b82a32bbe541e093401a89d890f5cf
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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