4-Nitrophenethyl bromide → 1-{8-[2-(4-nitrophenyl)ethyl]-3,8-diazabicyclo[3.2.1]oct-3-yl}-2-[4-(1H-tetrazol-1-yl)pheny]ethanone

HRID 2173445Notes

Reaction equation

[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9](=[O:22])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[N:20][N:19]=[N:18]3)=[CH:13][CH:12]=1)[CH2:2]2.Br[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C>C(#N)C>[N+:32]([C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][N:8]2[CH:5]3[CH2:6][CH2:7][CH:1]2[CH2:2][N:3]([C:9](=[O:22])[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]4[CH:21]=[N:20][N:19]=[N:18]4)=[CH:15][CH:16]=2)[CH2:4]3)=[CH:27][CH:28]=1)([O-:34])=[O:33]

Participants

Conditions

Temperature: 60 °C

Procedure

1-(3,8-Diazabicyclo[3.2.1]oct-3-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone (100 mg, 0.335 mmol) was combined with 1-(2-bromoethyl)-4-nitrobenzene (77 mg, 0.34 mmol) and Hunig's base (43.3 mg, 0.335 mmol) in acetonitrile (1 mL) and stirred at 60° C. for 5 h. Purification by mass-directed HPLC afforded the title compound. LC/MS: [(M+1)]+=448.

Workup

customPurification by mass-directed HPLC

Sources & evidence

ORD record: ord-fb462cf5fe504140b7fc7ab12c110a64
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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