Triethylamine → Adamantane-1-carboxylic acid (5-chloro-thiazol-2-yl)-amide
Reaction equation
[NH2:1][C:2]1[S:3][C:4]([Cl:7])=[CH:5][N:6]=1.[C:8]12([C:18](Cl)=[O:19])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1.C(OCC)(=O)C>[Cl:7][C:4]1[S:3][C:2]([NH:1][C:18]([C:8]23[CH2:17][CH:12]4[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]4)[CH2:15]2)[CH2:9]3)=[O:19])=[N:6][CH:5]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-amino-5-chlorothiazole (2.00 g, 14.9 mmol), 1-adamantanecarbonyl chloride (3.54 g, 17.8 mmol), 4-dimethylaminopyridine (1.10 g, 0.90 mmol) and triethylamine (4.15 mL, 23.0 mmol) in 80 mL of THF was stirred at 80° C. for 48 hours. The mixture was cooled to ambient temperature, diluted with 100 mL of ethyl acetate and washed with brine. The layers were separated and the aqueous phase was extracted twice with 50 mL of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, dichloromethane) afforded 2.27 g of the title compound: MS (DCI/NH3) m/z 297 (M+H)+.
Workup
- temperatureThe mixture was cooled to ambient temperature
- washwashed with brine
- customThe layers were separated
- extractionthe aqueous phase was extracted twice with 50 mL of ethyl acetate
- dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customPurification by column chromatography (SiO2, dichloromethane)
Sources & evidence
- ORD record
- ord-bda2508b03034f0f9d6e0795045818d3
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006275B2
Reaction notes
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