Dabco → 1-[4-(4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenoxymethyl)benzyl]-4-aza-1-azoniabicyclo[2.2.2]octane bromide

HRID 133713

Reaction equation

[Br:1][CH2:2][C:3]1[CH:39]=[CH:38][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[N:18]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:17](=[O:26])[CH:16]3[CH2:27][CH2:28][CH:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[OH:30])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[N:40]12[CH2:47][CH2:46][N:43]([CH2:44][CH2:45]1)[CH2:42][CH2:41]2>C1(C)C=CC=CC=1>[Br-:1].[F:25][C:22]1[CH:21]=[CH:20][C:19]([N:18]2[C:17](=[O:26])[CH:16]([CH2:27][CH2:28][CH:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[OH:30])[CH:15]2[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([CH2:2][N+:40]45[CH2:47][CH2:46][N:43]([CH2:44][CH2:45]4)[CH2:42][CH2:41]5)=[CH:39][CH:38]=3)=[CH:14][CH:13]=2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

180 mg of (12) and 300 mg of 1,4-diazabicyclo[2.2.2]octane (DABCO) were dissolved in 5 ml of toluene and stirred at 80° C. for 90 min. After the reaction ended, the mixture was allowed to cool and the colorless solid was filtered off with suction. This gave 195 mg of product (13) of molecular weight 704.66 (C38H40BrF2N3O3); MS (ESI): 624.30 (MH+).

Workup

temperatureto cool
filtrationthe colorless solid was filtered off with suction

Sources & evidence

ORD record: ord-f13b1760a6a04352ae89953cf810fe2c
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390790B2

Linked notes

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