Diisopropylethylamine → 2-(4,4-Diethyl-2-oxo-1,3-oxazolidin-3-yl)-4,5-dihydronaphtho[1,2-d][1,3]thiazole-7-carbonitrile

HRID 1436072Notes

Reaction equation

[CH2:1]([C:3]([NH:8][C:9]1[S:10][C:11]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:22]#[N:23])[CH:18]=3)[C:12]=2[N:13]=1)([CH2:6][OH:7])[CH2:4][CH3:5])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:1]([C:3]1([CH2:4][CH3:5])[CH2:6][O:7][C:34](=[O:36])[N:8]1[C:9]1[S:10][C:11]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:22]#[N:23])[CH:18]=3)[C:12]=2[N:13]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

2-{[1-Ethyl-1-(hydroxymethyl)propyl]amino}-4,5-dihydronaphtho[1,2-d][1,3]thiazole-7-carbonitrile (0.29 g, 0.89 mmol), prepared in the previous step, was dissolved in methylene chloride (10 mL) and diisopropylethyl amine (0.37 mL, 2.1 mmol) was added and the mixture was cooled to 0° C. Triphosgene (108 mg, 1.07 mmol) was added and the mixture was stirred for 2 h. The mixture was then diluted with methylene chloride and washed with 2N HCl, saturated NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (10%-15% ethyl acetate in hexane) afforded the title compound (230 mg, 73%) as a white solid. HRMS: calcd for C19H19N3O2S+H+, 354.12707. Found (ESI-FT/MS, [M+H]1+), 354.127; Analytical HPLC: purity 98.1% at 210-370 nm, 10.7 min.; 98.8% at 316 nm, 10.7 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 min.

Workup

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

Sources & evidence

ORD record: ord-8947c166a510459388ffc3419a85a52c
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618989B2

Reaction notes

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