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Chemical Structure| 922516-41-4 Chemical Structure| 922516-41-4

Structure of 922516-41-4

Chemical Structure| 922516-41-4

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Product Details of [ 922516-41-4 ]

CAS No. :922516-41-4
Formula : C11H17ClN2O2S
M.W : 276.78
SMILES Code : O=C(C1=CSC(C2CCNCC2)=N1)OCC.[H]Cl

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Application In Synthesis of [ 922516-41-4 ]

* 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 [ 922516-41-4 ]

[ 922516-41-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 345637-71-0 ]
  • [ 922516-41-4 ]
  • [ 922516-42-5 ]
YieldReaction ConditionsOperation in experiment
88% Example 1 : This example illustrates the preparation of 1 ,2,3,4-tetrahydro-naphthalene-1- carboxylic acid (2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}- thiazol-4-yl)-amide (Compound No. 1.g.01 1 ) a) Preparation of 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid ethyl esterTo a solution of <strong>[345637-71-0](5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid</strong> (9.1 g, 36.1 mmol) in DMF (100 ml.) is added diisopropylethylamine (45 ml_, 216 mmol), followed by O- (benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 ml_), washed with saturated aqueous sodium bicarbonate solution (300 ml_), 1 M HCI solution (300 ml_), and brine (100 ml_). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10:1 ) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1- yO-acetylJ-piperidin^-ylHhiazole^-carboxylic acid ethyl ester (13.6 g, 88 %). 1H-NMR (400 MHz, CDCI3): delta = 1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1 H), 3.22-3.43 (m, 1 H), 4.03-4.12 (m, 1 H), 4.42 (q, 3H), 4.54-4.69 (m, 1 H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1 H), 8.10 (br, 1 H). MS: m/z = 209 (M+1 ).
88% To a solution of <strong>[345637-71-0](5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid</strong> (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O- (benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1 M HCI solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10: 1) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)- acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester (13.6 g, 88 %). 1 H-NMR (400 - -MHz, CDCI3): delta = 1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1 H), 3.22-3.43 (m, 1 H), 4.03-4.12 (m, 1 H), 4.42 (q, 3H), 4.54-4.69 (m, 1 H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1 H), 8.10 (br, 1 H). MS: m/z = 209 (M+1).
88% a) Preparation of 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole- 4-carboxylic acid ethyl esterTo a solution of <strong>[345637-71-0](5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid</strong> (9.1 g, 36.1 mmol) in DMF (100 ml_) is added diisopropylethylamine (45 ml_, 216 mmol), followed by 0-(benzotriazol- 1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 ml_), washed with saturated aqueous sodium bicarbonate solution (300 ml_), 1 M HCI solution (300 ml_), and brine (100 ml_). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10: 1 ) to give 2-{1 -[2-(5-methyl-3-trif luoromethyl-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-thiazole-4- carboxylic acid ethyl ester (13.6 g, 88 %). 1 H-NMR (400 MHz, CDCI3): delta = 1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1 H), 3.22-3.43 (m, 1 H), 4.03-4.12 (m, 1 H), 4.42 (q, 3H), 4.54-4.69 (m, 1 H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1 H), 8.10 (br, 1 H). MS: m/z = 209 (M+1).
88% a) Preparation of 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester To a solution of <strong>[345637-71-0](5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid</strong> (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1M HCl solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10:1) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester (13.6 g, 88%). 1H-NMR (400 MHz, CDCl3): delta=1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1H), 3.22-3.43 (m, 1H), 4.03-4.12 (m, 1H), 4.42 (q, 3H), 4.54-4.69 (m, 1H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1H), 8.10 (br, 1H). MS: m/z=209 (M+1).
a) Preparation of 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid ethyl ester To a solution of <strong>[345637-71-0](5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid</strong> (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O- (benzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1 M HCI solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10:1 ) to give 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazol-1 - yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester. 1H-NMR (400 MHz, CDCI3): delta = 1.40 (t, 3H), 1 .70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1 H), 3.22- 3.43 (m, 1 H), 4.03-4.12 (m, 1 H), 4.42 (q, 3H), 4.54-4.69 (m, 1 H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1 H), 8.10 (br, 1 H). MS: m/z = 209 (M+1 ).

  • 2
  • [ 345637-71-0 ]
  • [ 922516-41-4 ]
  • [ 125700-67-6 ]
  • [ 922516-42-5 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; a) Preparation of 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester To a solution of <strong>[345637-71-0](5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid</strong> (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1M HCl solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10:1) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetyl]piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester. 1H-NMR (400 MHz, CDCl3): delta=1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1H), 3.22-3.43 (m, 1H), 4.03-4.12 (m, 1H), 4.42 (q, 3H), 4.54-4.69 (m, 1H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1H), 8.10 (br, 1H). MS: m/z=209 (M+1).
 

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