HCID 90403394, compound → HCID 178433219, compound

HRID 1049379Notes

Reaction equation

HRID 1049379 reaction equation
C(OC[N:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[C:22]([CH3:37])=[N:23][C:24]([NH:27][C:28]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[O:29])=[CH:25][CH:26]=3)[CH:17]=[CH:16][N:15]=2)[N:11]=[N:10]1)(=O)C(C)(C)C>CO>[NH:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31](=[O:36])[C:32]([CH3:34])([CH3:33])[CH3:35])=[O:29])=[N:23][C:22]=3[CH3:37])[CH:17]=[CH:16][N:15]=2)[N:11]=[N:10]1

Participants

3

Reactant 1

HCID 90403394HCID 90403394, compound

Product 1

HCID 178433219HCID 178433219, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (4-(4-((2-Methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate (0.16 g, 0.314 mmol) and TEA (0.175 mL, 1.256 mmol) in MeOH (5 mL) was stirred at 40° C. for ˜40 h. The solvent was evaporated to dryness and the residue was purified by silica gel chromatography (MeOH/DCM), and lyophilized from MeCN/H2O to afford N-((5-((2-(1H-1,2,3-triazol-4-yl)pyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamide (62 mg, 50%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.18 (s, 1H), 10.40 (br s, 1H), 8.49 (d, J=5.9 Hz, 1H), 8.23 (br s, 1H), 7.93 (br s, 1H), 7.70 (d, J=8.8 Hz, 1H), 7.35 (br s, 1H), 6.90 (d, J=5.5 Hz, 1H), 2.26 (s, 3H), 1.21 (s, 9H); MS (ESI) m/z: 396.2 (M+H+).

Workup

  1. customThe solvent was evaporated to dryness
  2. customthe residue was purified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-3fec5dd690fd4dab8b1ef046285885e5
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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