Triethylamine → 4-[5-Chloro-2-(4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile

HRID 1436437Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=[N:4][C:3]=1[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.C(N(CC)CC)C.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([N:7]2[C:8]([CH3:12])([CH3:11])[CH2:9][O:10][C:29]2=[O:31])=[N:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([C:17]#[N:18])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-{5-Chloro-2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile (0.93 g, 3.0 mmol), prepared in the previous step, was dissolved in methylene chloride (25 mL), triethylamine (4.15 mL, 30 mmol) was added and the mixture was cooled to 0° C. Triphosgene (1.79 g, 6.0 mmol) was added and the mixture was stirred for 2 h. The mixture was then diluted with methylene chloride, washed with 2N HCl, saturated NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (10% acetone/hexane) afforded the title compound (220 mg, 22%) as a pale yellow solid. HRMS: calcd for C15H12ClN3O2S+H+, 334.04115; found (ESI, [M+H]+), 334.04; HPLC purity 100% at 210-370 nm, 10.6 min; 100% at 244 nm, 10.6 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 mm.

Workup

washwashed with 2N HCl, saturated NaHCO3, brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1fe8cc41ffae45aa8ecfdcb325b9a1a1
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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