N-chlorosuccinamide → 4'-(5-Amino-6-chloropyrazin-2-yl)-N-tert-butyl-3'-fluorobiphenyl-2-sulfonamide

HRID 1523951Notes

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.[Cl:29]NC(=O)CCC(N)=O>CN(C=O)C>[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]([CH3:25])([CH3:27])[CH3:26])(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:28])=[N:6][C:7]=1[Cl:29]

Participants

Conditions

Temperature: 60 °C

Procedure

To a 25 mL round-bottomed flask were added a stirbar, 52 mg (0.13 mmol) 4′-(5-aminopyrazin-2-yl)-N-tert-butyl-3′-fluorobiphenyl-2-sulfonamide, 27 mg (0.20 mmol) N-chlorosuccinamide, and dry DMF (2.0 mL). The flask was sparged with nitrogen and heated at 60° Celsius for 18 hours before cooling to rt and subjecting the reaction mixture (after syringe filtration) to HPLC purification to give the title compound (29.6 mg, 52%). MS (ESI): mass calcd. for C20H20ClFN4O2S, 434.10; m/z found, 435.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6) δ 8.44 (d, J=2.0, 1H), 8.06 (dd, J=8.1, 1.5, 1H), 7.85 (dd, J=9.4, 6.8, 1H), 7.70-7.64 (m, 1H), 7.64-7.57 (m, 1H), 7.43-7.27 (m, 3H), 7.13 (s, 2H), 6.98 (d, J=3.7, 1H), 1.02 (s, 9H).

Workup

customThe flask was sparged with nitrogen
temperaturebefore cooling to rt
filtrationthe reaction mixture (after syringe filtration)
customto HPLC purification

Sources & evidence

ORD record: ord-e983671a9a8b4e8a95bb4cc8c2d7a8e9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079866B2

Reaction notes

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