N-bromobutanimide → HCID 58994541, compound

HRID 1190227Notes

Reaction equation

[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:32])C(=O)C1>CC#N>[Br:32][C:18]1[CH:17]=[C:16]([CH2:15][N:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:24])[CH3:23])[CH2:14][CH2:13]2)[CH:21]=[CH:20][C:19]=1[NH2:22]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-piperazin-1-ylmethyl}-phenylamine (as prepared in the previous step, 204 mg, 0.582 mmol) in CH3CN (6 mL) was cooled to 0° C. and treated dropwise with NBS as a solution in CH3CN (6 mL). The solvents were evaporated in vacuo. The residue was taken up in EtOAc and washed with satd aq NaHCO3. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of the residue on a 20-g Isolute SPE column on a FlashMaster system with 25-50% EtOAc-hexane afforded the title compound (80.9 mg, 32%) as an off-white solid. Mass spectrum (ESI, m/z): Calcd. for C19H34N3OSiBr, 428.2/430.2 (M+H). found 428.1/430.0.

Workup

customThe solvents were evaporated in vacuo
washwashed with satd aq NaHCO3
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue on a 20-g Isolute SPE column on a FlashMaster system with 25-50% EtOAc-hexane

Sources & evidence

ORD record: ord-5a6e831f19cd45129c3d25d09f1c0b28
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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