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Chemical Structure| 690261-84-8 Chemical Structure| 690261-84-8

Structure of 690261-84-8

Chemical Structure| 690261-84-8

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Product Details of [ 690261-84-8 ]

CAS No. :690261-84-8
Formula : C10H11F3O
M.W : 204.19
SMILES Code : O=C(OC(C)(C)C)N1CCC(C2N=C(N)SC=2)CC1
MDL No. :MFCD07773046

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Application In Synthesis of [ 690261-84-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 690261-84-8 ]

[ 690261-84-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 17356-08-0 ]
  • [ 301221-79-4 ]
  • [ 690261-84-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethanol; at 60℃; for 8h; The bromomethylketone prepared as described in Steps A through C of the synthesis of Intermediate 14 (1.68 g, 5.47 mmol) was combined with thiourea (625 mg, 8.21 mmol) and potassium carbonate (1.51 g, 10.9 mmol) in ethanol and the resulting mixture was stirred at 60 °C for 8 h. The reaction mixture was then concentrated and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted again with ethyl acetate and the combined organic layers were washed with brine, dried over anhydrous MGS04, filtered, and concentrated to give 1.42 g of crude aminothiazole product.
In isopropyl alcohol; at 20℃; for 1h; a) Preparation of 4-(2-amino-thiazol-4-yl)-piperidine-1 -carboxylic acid tert-butyl ester A suspension of thiourea (7.7g, 0.1 mol) in 520 ml of isopropanol is slowly added to a solution of <strong>[301221-79-4]4-(2-bromo-acetyl)-piperidine-1-carboxylic acid tert-butyl ester</strong> (14.3 g, 50.5 mmol) in 260 ml of isopropanol. The reaction mixture is stirred for 1 h at room temperature and subsequently poured slowly into 500 ml of a 1 N aqueous sodium carbonate solution, keeping the temperature between 20 and 30 °C by ice cooling. After separation of the phases, the aqueous layer is extracted twice with ethyl acetate. The combined organic phase is washed with brine and with water, dried over sodium sulfate and evaporated to dryness, delivering directly 4-(2-amino-thiazol-4-yl)-piperidine-1 -carboxylic acid tert-butyl ester as beige cristals. 1H-NMR (400 MHz, CDCI3): delta = 1.46 (s, 9H), 1.53 (dd, 2H), 1 .95 (dd, 2H), 2.61 - 2.82 (m, 3H), 4.14 (bs, 2H), 4.88 - 4.93 (m, 2H), 6.09 (s, 1 H). MS: m/z = 284 (M+1 ).
In isopropyl alcohol; at 20℃; for 1h; a) Preparation of 4-(2-amino-thiazol-4-yl)piperidine-1-carboxylic acid tert-butyl ester A suspension of thiourea (7.7 g, 0.1 mol) in 520 ml of isopropanol is slowly added to a solution of <strong>[301221-79-4]4-(2-bromo-acetyl)-piperidine-1-carboxylic acid tert-butyl ester</strong> (14.3 g, 50.5 mmol) in 260 ml of isopropanol. The reaction mixture is stirred for 1 h at room temperature and subsequently poured slowly into 500 ml of a 1 N aqueous sodium carbonate solution, keeping the temperature between 20 and 30° C. by ice cooling. After separation of the phases, the aqueous layer is extracted twice with ethyl acetate. The combined organic phase is washed with brine and with water, dried over sodium sulfate and evaporated to dryness, delivering directly 4-(2-amino-thiazol-4-yl)piperidine-1-carboxylic acid tert-butyl ester as beige crystals. 1H-NMR (400 MHz, CDCl3): delta=1.46 (s, 9H), 1.53 (dd, 2H), 1.95 (dd, 2H), 2.61-2.82 (m, 3H), 4.14 (bs, 2H), 4.88-4.93 (m, 2H), 6.09 (s, 1H). MS: m/z=284 (M+1).
 

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