Dimethylamine → N-(3-(1-(Dimethylamino)-2-hydroxyethyl)phenyl)-2',4'-difluorobiphenyl-4-sulfonamide

HRID 221396Notes

Reaction equation

HRID 221396 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.[CH3:28][NH:29][CH3:30]>C(O)C>[CH3:28][N:29]([CH3:30])[CH:25]([C:21]1[CH:20]=[C:19]([NH:18][S:15]([C:12]2[CH:13]=[CH:14][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:24]=[CH:23][CH:22]=1)[CH2:27][OH:26]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 866562622',4'-Difluoro-N-(3-(oxiran-2-yl)phenyl)biphenyl-4-sulfonamide

Product 1

HCID 45138189N-(3-(1-(Dimethylamino)-2-hydroxyethyl)phenyl)-2',4'-difluorobiphenyl-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using a method analogous to Method D, using 2′,4′-difluoro-N-(3-(oxiran-2-yl)phenyl)biphenyl-4-sulfonamide and 33% dimethylamine in ethanol, 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 from the mixture of isomers as gave ABD784. 1H NMR (300 MHz, CDCl3): δ 2.08 (6H, s), 3.40 (3H, m), 3.48 (1H, m), 3.62-3.64 (1H, m), 6.87-6.96 (3H, m), 7.04-7.12 (2H, m), 7.20-7.25 (1H, m), 7.33-7.40 (1H, m), 7.53 (2H, d, J=8 Hz) and 7.78 (2H, d, J=8 Hz). MS, m/z: Calcd, 432.132. Found, 432.56 (M).

Workup

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

Sources & evidence

ORD record
ord-8e5b537ffdef485591e1b715044ad490
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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