Acetic Acid → HCID 178525492, compound

HRID 2174360Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1)#[N:2].CC(O)=O.CCN(CC)CC.[N-:44]=[N+:45]=[N-:46].[Na+].Cl>O.CN(C=O)C>[NH:44]1[C:1]([C:3]2[CH:8]=[CH:7][C:6]([C:9]3[O:13][N:12]=[C:11]([C:14]4[CH:19]=[CH:18][C:17]([C:20]5[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:22][CH:21]=5)=[CH:16][CH:15]=4)[N:10]=3)=[CH:5][CH:4]=2)=[N:2][N:46]=[N:45]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-(4′-{5-[4-cyanophenyl]-[1,2,4]oxadiazol-3-yl}biphenyl-4-yloxy)butyric acid (3.17 g, 7.45 mmol), DMF (15 ml), AcOH (2.25 ml, 37.5 mmol), NEt3 (5.0 ml, 36 mmol), and NaN3 (2.89 g, 44.5 mmol) was stirred at 140° C. After 24 h water (150 ml) and concentrated hydrochloric acid (6 ml) were added. The product was isolated by filtration, washed with water, resuspended in MeCN (100 ml), heated to reflux (it did not dissolve completely), homogenized, and allowed to cool to room temperature. Filtration yielded 2.50 g (72%) of 4-(4′-{5-[4-(5-tetrazolyl)phenyl]-[1,2,4]oxadiazol-3-yl}biphenyl-4-yloxy)butyric acid as a solid.

Workup

customThe product was isolated by filtration
washwashed with water
temperatureheated
temperatureto reflux (it
dissolutiondid not dissolve completely),
stirringhomogenized
temperatureto cool to room temperature
filtrationFiltration

Sources & evidence

ORD record: ord-70527ce9d6bc4af7bc950cb4f0efff8f
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061067B2

Reaction notes

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