Diethanolamine → 2-[{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}(2-hydroxyethyl)amino]ethanol

HRID 2407484Notes

Reaction equation

C(N(C(C)C)CC)(C)C.[NH:10]([CH2:14][CH2:15][OH:16])[CH2:11][CH2:12][OH:13].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:29]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[C:32]([F:42])[CH:31]=3)[O:27][N:26]=2)=[CH:21][CH:20]=1>CN(C)C=O>[F:42][C:32]1[CH:31]=[C:30]([C:28]2[O:27][N:26]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([CH2:18][N:10]([CH2:14][CH2:15][OH:16])[CH2:11][CH2:12][OH:13])=[CH:20][CH:21]=3)[N:29]=2)[CH:35]=[CH:34][C:33]=1[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Diisopropylethylamine (23.5 mL, 0.136 mol) and diethanolamine (14.2 g, 0.135 mol) are added to a stirred solution of 3-(4-chloromethylphenyl)-5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole (33 g, 0.090 mol) in N,N-dimethyl-formamide (200 mL). The reaction mixture is heated at 90° C. for 2.5 hrs, the solvent is removed under reduced pressure and the residue is treated with demineralized water (200 mL) to get a solid which is filtered and washed with n-hexane (150 mL) and diethyl ether (100 mL) to furnish 2-[{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}(2-hydroxyethyl)amino]ethanol.

Workup

customthe solvent is removed under reduced pressure
additionthe residue is treated with demineralized water (200 mL)
customto get a solid which
filtrationis filtered
washwashed with n-hexane (150 mL) and diethyl ether (100 mL)

Sources & evidence

ORD record: ord-e3c168f02d6d4e668c789ad546ba97cc
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809539B2

Reaction notes

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