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

HRID 1524149Notes

Reaction equation

HRID 1524149 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([S:20]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:28])=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[C:24]([NH:23][S:20]([C:15]1[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([N:1]([S:20]([CH3:15])(=[O:22])=[O:21])[S:39]([CH3:38])(=[O:41])=[O:40])=[CH:7][N:6]=3)=[C:9]([F:28])[CH:10]=2)=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:22])=[O:21])([CH3:25])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 778446974'-(5-aminopyrazin-2-yl)-N-tert-butyl-3'-fluorobiphenyl-2-sulfonamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 mL vial were added a stir-bar, 4′-(5-aminopyrazin-2-yl)-N-(tert-butyl)-3′-fluoro-[1,1′-biphenyl]-2-sulfonamide (49 mg, 0.12 mmol), dry DCM (2.0 mL), DIPEA, (0.10 mL, 0.58 mmol), and methanesulfonyl chloride (0.020 mL, 0.25 mmol). The mixture was stirred at rt for 17.25 h before subjecting it to FCC to give impure title compound. The product was used in the next step without further purification.

Workup

  1. additionTo a 20 mL vial were added a stir-bar

Sources & evidence

ORD record
ord-e9e899dad28444c9a2102708c2c291f3
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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