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

HRID 1874429Notes

Reaction equation

HRID 1874429 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[CH:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1.[N:24]([C:27](OCC)=O)=C=S.[Cl-].O[NH3+].C([N:38](CC)C(C)C)(C)C>CO.C(O)C.CS(C)=O>[NH2:38][C:27]1[N:1]=[C:2]2[CH:3]=[CH:4][C:5]([O:8][C:9]3[CH:10]=[C:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:12]=[CH:13][C:14]=3[CH3:15])=[CH:6][N:7]2[N:24]=1

Participants

8

Reactant 4

HCID 21645Hydroxylamine HClHCID 81531DiisopropylethylamineHCID 85320Ethyl isothiocyanatoformateHCID 57749176Tert-butyl {3-[(6-aminopyridin-3-yl)oxy]-4-methylphenyl}carbamate

Product 1

HCID 57749391Tert-butyl {3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}carbamateYield 87%

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]-4-methylphenyl}carbamate (1.69 g, 5.35 mmol), DMSO (5 mL), ethyl isothiocyanatoformate (843 mg, 6.42 mmol), ethanol (20 mL), methanol (20 mL), hydroxylammonium chloride (2.43 g, 35.0 mmol) and N,N-diisopropylethylamine (4.35 mL, 25.0 mmol) as starting materials, the title compound (1.55 g, 87%) was obtained as a white solid.

Sources & evidence

ORD record
ord-4db9f563c2f542eb90a1e5ba9c8f4e56
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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