N-bromobutanimide → 2-Bromo-4-(cis-3,5-dimethyl-piperazine-1-sulfonylmethyl)-phenylamine

HRID 1190119Notes

Reaction equation

[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([S:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH2:3]1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)Cl>[Br:27][C:17]1[CH:18]=[C:13]([CH2:12][S:9]([N:4]2[CH2:5][C@H:6]([CH3:8])[NH:7][C@H:2]([CH3:1])[CH2:3]2)(=[O:11])=[O:10])[CH:14]=[CH:15][C:16]=1[NH2:19]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 283 mg (0.999 mmol) of 4-(cis-3,5-dimethyl-piperazine-1-sulfonylmethyl)-phenyl amine (as prepared in the previous step) in CH2Cl2 (15 mL) was cooled to −78° C. and treated portionwise with 176 mg (0.989 mmol) of NBS. The mixture was stirred at −78° C. for 1 h and at RT for 2 h. The mixture was diluted with CH2Cl2 (15 mL) and washed with saturated aqueous NaHCO3 (1×20 mL) and brine (1×20 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 356 mg (98%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C13H20N3O2SBr, 362.0/364.0 (M+H). found 361.8/363.3.

Workup

washwashed with saturated aqueous NaHCO3 (1×20 mL) and brine (1×20 mL)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9efe1d5be81a484d9f6be0759b5f2b10
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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