Sodium Hydroxide → N-(tert-Butyl)-3'-fluoro-4'-(5-(methylsulfonamido)pyrazin-2-yl)-[1,1'-biphenyl]-2-sulfonamide

HRID 1524150Notes

Reaction equation

HRID 1524150 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[N:25][C:24]([N:27](S(C)(=O)=O)[S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][N:22]=3)=[C:17]([F:36])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CS(C)=O>[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[N:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][N:22]=3)=[C:17]([F:36])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:7])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131733124N-(tert-Butyl)-3'-fluoro-4'-(5-(N-(methylsulfonyl)methylsulfonamido) pyrazin-2-yl)-[1,1'-biphenyl]-2-sulfonamide

Product 1

HCID 90313735N-(tert-Butyl)-3'-fluoro-4'-(5-(methylsulfonamido)pyrazin-2-yl)-[1,1'-biphenyl]-2-sulfonamideYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 20 mL vial containing N-(tert-butyl)-3′-fluoro-4′-(5-(N-(methylsulfonyl)methylsulfonamido)pyrazin-2-yl)-[1,1′-biphenyl]-2-sulfonamide (38 mg, 0.068 mmol) were added a stir-bar and DMSO (1 mL). The mixture was sonicated until homogeneous, and then treated with NaOH (0.23 mL, 0.23 mmol, 1.0 N). The mixture was stirred at rt for 18.7 h before passing it through a syringe filter and subjecting it to HPLC purification thus yielding the title compound (28 mg, 86%). MS (ESI): mass calcd. for C21H23FN4O4S2, 478.11; m/z found, 479.1 [M+H]+. 1H NMR (600 MHz, DMSO-δ6) δ 11.29 (s, 1H), 8.82-8.72 (m, 1H), 8.46 (d, J=1.5, 1H), 8.07 (dd, J=7.9, 1.4, 1H), 7.98-7.91 (m, 1H), 7.71-7.65 (m, 1H), 7.65-7.58 (m, 1H), 7.43-7.32 (m, 3H), 7.05 (s, 1H), 3.41 (s, 3H), 1.03 (s, 9H).

Workup

  1. additionwere added a stir-bar
  2. customThe mixture was sonicated until homogeneous, and
  3. filtrationfilter
  4. customto HPLC purification

Sources & evidence

ORD record
ord-c5ef6f54bac04480a02d815944edda92
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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