Sodium Azide → HCID 59463204, compound

HRID 1712971Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-{[5-(2-hydroxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-1-yl]carbonyl}thiophene-2-carbonitrile (0.300 g, 0.60 mmol) in DMF (5 mL) was added sodium azide (0.120 g, 1.80 mmol) and aluminum trichloride (0.240 g, 1.80 mmol). The reaction mixture was allowed to stir at 100° C. overnight and then concentrated. The residue was purified by column chromatography to give 2-(3-pyridin-3-yl-1-{[5-(2H-tetrazol-5-yl)-2-thienyl]carbonyl}-4,5-dihydro-1H-pyrazol-5-yl)phenol (I-226). LCMS: (FA) ES+ 436, ES-434.

Workup

concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-91d80b62a78345e2aee3a13ac69d77d7
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795249B2

Reaction notes

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