Ammonia → Tert-butyl 3-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenylcarbamate

HRID 578138Notes

Reaction equation

HRID 578138 reaction equation
[OH:1][N:2]=[C:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](O)=O)=[O:17])([CH3:14])([CH3:13])[CH3:12].N>>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:3]2[N:10]=[C:22]([C:21]3[CH:20]=[C:19]([NH:18][C:16](=[O:17])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])[CH:27]=[CH:26][CH:25]=3)[O:1][N:2]=2)[CH:5]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 308113N-HydroxynicotinimidamideHCID 8541623-(((Tert-butoxy)carbonyl)amino)benzoic acid

Product 1

HCID 67026126Tert-butyl 3-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenylcarbamate

Procedure

The title compound was prepared according to the procedure of Example 8 using N′-hydroxynicotinimidamide (Aldrich) and 3-(tert-butoxycarbonylamino)benzoic acid (Aldrich). 1H NMR (300 MHz, CDCl3) δ 1.56 (s, 9H), 6.71 (s, 1H), 7.39-7.58 (m, 2H), 7.68 (d, J=7.9 Hz, 1H), 7.89 (d, J=9.1 Hz, 1H), 8.24 (s, 1H), 8.45 (d, J=7.9 Hz, 1H), 8.77 (d, J=4.8 Hz, 1H), 9.40 (s, 1H) ppm; MS (DCI/NH3) m/z 339 (M+H)+, 356 (M+NH4)+.

Sources & evidence

ORD record
ord-d046024d99fe49f4bf49e249572c3649
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

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