Acetic Acid → HCID 77230640, compound

HRID 2173382Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](CC([O-])=O)C=[CH:4][CH:3]=1.[CH:12]([O:19][CH2:20][CH3:21])(OCC)OCC.[N-:22]=[N+:23]=[N-:24].[Na+].C(=O)(O)[O-:27].[Na+].[C:31](O)(=O)[CH3:32]>O>[N:7]1([C:2]2[N:1]=[C:32]([CH2:21][C:20]([O:19][CH3:12])=[O:27])[CH:31]=[CH:4][CH:3]=2)[CH:6]=[N:24][N:23]=[N:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (6-aminopyridin-2-yl)acetate (375 mg, 2.26 mmol) in glacial acetic acid (5 mL) was added triethyl orthoformate (1.13 mL, 6.77 mmol) and sodium azide (440 mg, 6.77 mmol). The reaction mixture was heated at 80° C. for 3 hours in a sealed vial and then cooled to ambient temperature. Once cooled, water (5 mL) and solid sodium bicarbonate were added until a pH range of 6-7 was achieved. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified via MPLC (0-100% EtOAc/Hex gradient) to afford methyl [6-(1H-tetrazol-1-yl)pyridin-2-yl]acetate. 1H NMR (500 MHz, DMSO-d6): 10.1 (s, 1H), 8.2 (t, 1H), 8 (d, 1H), 7.6 (d, 1H), 4.0 (s, 3H), 3.6 (s, 2H). (M+H−28)+192.

Workup

temperaturethen cooled to ambient temperature
temperatureOnce cooled
extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
dry with materialThe combined organic layers were then dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified via MPLC (0-100% EtOAc/Hex gradient)

Sources & evidence

ORD record: ord-f6c4110846514af7844bb23c01b70d9e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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