Methylamine → 2',4'-Difluoro-N-(3-(2-hydroxy-1-(methylamino)ethyl)phenyl)biphenyl-4-sulfonamide

HRID 221395Notes

Reaction equation

HRID 221395 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][NH2:29]>C(O)C>[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]([NH:29][CH3:28])[CH2:27][OH:26])[CH:20]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 866562622',4'-Difluoro-N-(3-(oxiran-2-yl)phenyl)biphenyl-4-sulfonamide

Product 1

HCID 673287382',4'-Difluoro-N-(3-(2-hydroxy-1-(methylamino)ethyl)phenyl)biphenyl-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% methylamine in ethanol, the title compound was obtained as a light orange powder (165 mg) by flash chromatography of mixture of regioisomers which gave ABD783. 1H NMR (400 MHz, CDCl3): δ 2.10 (3H, s), 3.51 (1H, m), 3.60-3.62 (2H, m), 5.10 (3H, br s), 6.70-6.95 (3H, m), 7.10-7.15 (4H, m), 7.20-7.25 (1H, m), 7.34 (2H, d, J=8 Hz) and 7.73 (2H, d, J=8 Hz). MS, m/z: Calcd, 418.11. Found, 418.09 (M).

Sources & evidence

ORD record
ord-e924b4bcaa5342a1ba20ae10a1d2584b
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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