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 348044

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-415c9c1ff1584f0989e8ec94edd54a7c
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176194B2

Linked notes

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