Hydroxylamine HCl → Tert-butyl {3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}carbamate

HRID 1874473Notes

Reaction equation

HRID 1874473 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[N:23]([C:26](OCC)=O)=C=S.[Cl-].O[NH3+].C([N:37](CC)C(C)C)(C)C>CO.C(O)C.CS(C)=O>[NH2:37][C:26]1[N:1]=[C:2]2[CH:3]=[CH:4][C:5]([O:8][C:9]3[CH:10]=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH:12]=[CH:13][CH:14]=3)=[CH:6][N:7]2[N:23]=1

Participants

8

Reactant 4

HCID 21645Hydroxylamine HClHCID 81531DiisopropylethylamineHCID 85320Ethyl isothiocyanatoformateHCID 57749334Tert-butyl 3-(6-aminopyridin-3-yloxy)phenylcarbamate

Product 1

HCID 57749279Tert-butyl {3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}carbamateYield 94%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

In the same manner as in Example 17-1 and using tert-butyl {3-[(6-aminopyridin-3-yl)oxy]phenyl}carbamate (15.0 g, 49.8 mmol), ethyl isothiocyanatoformate (7.18 g, 54.8 mmol), DMSO (50 mL), hydroxylammonium chloride (11.8 g, 170 mmol), N,N-diisopropylethylamine (21.2 mL, 122 mmol), ethanol (70 mL) and methanol (70 mL) as starting materials, the title compound (10.5 g, 94%) was obtained as a white solid.

Sources & evidence

ORD record
ord-67168c839fcc4a498f73b6428604e2d4
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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