Tert-butyl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate → N-((5-((2-aminopyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamide

HRID 626572Notes

Reaction equation

HRID 626572 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15]C(=O)OC(C)(C)C)[CH:10]=2)=[CH:6][CH:5]=[C:4]([NH:23][C:24]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:25])[N:3]=1>C(O)(C(F)(F)F)=O>[NH2:15][C:11]1[CH:10]=[C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:23][C:24]([NH:26][C:27](=[O:32])[C:28]([CH3:30])([CH3:29])[CH3:31])=[O:25])=[N:3][C:2]=2[CH3:1])[CH:14]=[CH:13][N:12]=1

Participants

3

Reactant 1

HCID 131735227Tert-butyl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate

Product 1

HCID 90410520N-((5-((2-aminopyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamideYield 98%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate (0.370 g, 0.834 mmol in TFA (5 mL) was stirred at RT for 0.5 h and concentrated to dryness to afford N-((5-((2-aminopyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamide (280 mg, 98%). MS (ESI) m/z: 344.2 (M+H+).

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3335abba83b643399b62ecb95fd29757
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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