Hydrochloric Acid → N4-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-aminoisonicotinamide

HRID 1828441Notes

Reaction equation

[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18]C(=O)C)[CH:13]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C(O)C>[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 85 °C

Procedure

N4-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-(acetylamino)isonicotinamide (546 mg) dissolved in ethanol (12 ml) was added dropwise with concentrated hydrochloric acid (1.2 ml) at room temperature and stirred at 80-90° C. for 1 hour. The reaction solution was returned to room temperature, concentrated under reduced pressure, neutralized with 1 N sodium hydroxide and extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=60:1→20:1) to obtain 247.2 mg (52%) of the title compound as white crystals.

Workup

customwas returned to room temperature
concentrationconcentrated under reduced pressure
extractionextracted with chloroform
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=60:1→20:1)

Sources & evidence

ORD record: ord-a4174dac4bad4b44b79eb207637c13c5
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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