Triethylamine → HCID 22063585, compound

HRID 1828504Notes

Reaction equation

[C:1]([C:5]1[N:6]=[C:7]([CH:10](O)[CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:13]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.N12CCCN=C1CCCCC2>O1CCCC1>[C:1]([C:5]1[N:6]=[C:7](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:13]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

The tert-butyl N-(4-{2-[4-(tert-butyl)-1,3-thiazol-2-yl]-2-hydroxyethyl}-2-pyridyl)carbamate (1.80 g, 4.77 mmol) obtained in (C) was dissolved in anhydrous tetrahydrofuran (20 ml), added with triethylamine (2.33 ml, 16.7 mmol) and methanesulfonyl chloride (738 μl, 9.54 mmol), and stirred at 0° C. for 3.5 hours. After insoluble solids were removed, the reaction mixture was washed with tetrahydrofuran, and the solvent was evaporated under reduced pressure. The residue was dissolved in toluene (30 ml), added with 1,8-diazabicyclo[5.4.0]undec-7-ene (1.07 ml, 7.15 mmol), and refluxed by heating for 1 hour. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→2:1, v/v) to obtain the title compound (1.23 g, 72%).

Workup

customAfter insoluble solids were removed
washthe reaction mixture was washed with tetrahydrofuran
customthe solvent was evaporated under reduced pressure
dissolutionThe residue was dissolved in toluene (30 ml)
temperaturerefluxed
temperatureby heating for 1 hour
concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography (n-hexane

Sources & evidence

ORD record: ord-675d5715f9cc443c8a570b6f9417da02
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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