1612172-62-9|1-(Cyclopropanesulfonyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole| Ambeed

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Quality Control of [ 1612172-62-9 ] Purity: 98% SDS Specification

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Product Details of [ 1612172-62-9 ]

CAS No. :	1612172-62-9
Formula :	C₁₂H₁₉BN₂O₄S
M.W :	298.17
SMILES Code :	CC1(C)OB(OC1(C)C)C2=CN(N=C2)S(=O)(C3CC3)=O
MDL No. :	MFCD29763678
InChI Key :	CWOOICDCNKJNSS-UHFFFAOYSA-N
Pubchem ID :	90177577

Safety of [ 1612172-62-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 1612172-62-9 ]

* 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 [ 1612172-62-9 ]

[ 1612172-62-9 ] Synthesis Path-Downstream 1~30

1
[ 1612172-54-9 ]
[ 1612172-62-9 ]
[ 1612164-61-0 ]

Yield	Reaction Conditions	Operation in experiment
5%	With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium carbonate; In acetonitrile; at 100℃; for 3h;	To a glass vial was added : l-(cyclopropylsulfonyl)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-lH-pyrazole (Example 51, step 6) (0.56 g, 1.8 mmol), N-(2-chloropyrimidin-4-yl)-l- isopropyl-2-methyl-lH-imidazo[4,5-c]pyridin-6-amine (Example 46, Step 7) (0.56 g, 1.8 mmol), Pd(Amphos)2Cl2 (65 mg, 0.092 mmol), a 2M solution of Na2C03 (1.4 mL, 2.8 mmol) and acetonitrile (2.5 mL). The mixture was degassed by nitrogen bubbling for 20 min. The reaction vial was sealed and stirred at 100 C in an oil bath for 3 h. The reaction mixture was cooled to room temperature, filtered and concentrated. The crude product was purified by reverse-phase HPLC and lyophilized to give the title compound (41 mg, 5 %). LCMS (ESI): RT 4.77 min, [M+H]+ 439.2, method = B; lH NMR (400 MHz, DMSO-d6) δ 10.16 (s, 1H), 8.66 (s, 1H), 8.56 (d, J= 0.8 Hz, 1H), 8.47 (d, J= 0.5 Hz, 1H), 8.39 (m, 2H), 7.24 (s, 1H), 4.78 (m, 1H), 2.58 (s, 3H), 1.63 (d, J= 6.9 Hz, 6H), 1.38 - 1.21 (m, 4H).

References: [1]Patent: WO2014/81718,2014,A1 .Location in patent: Page/Page column 126.
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 9080 - 9093.

2
[ 1612172-61-8 ]
[ 1612172-62-9 ]
[ 1612164-60-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium carbonate; In acetonitrile; at 100℃; for 1h;Inert atmosphere;	To a glass vial was added : l-(cyclopropylsulfonyl)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-lH-pyrazole (95 mg, 0.30 mmol), 6-((2-chloropyrimidin-4-yl)amino)-l-isopropyl-lH- pyrrolo[3,2-c]pyridine-3-carboxamide (50 mg, 0.15 mmol), Pd(Amphos)2Cl2 (5 mg, 0.008 mmol), a 2M solution of Na2C03 (0.11 mL, 0.23 mmol) and acetonitrile (2.5 mL). The mixture was degassed by nitrogen bubbling for 20 min. The reaction vial was sealed and stirred at 100 C in an oil bath for 1 h. The reaction mixture was cooled to room temperature, filtered and concentrated. The crude product was purified by reverse-phase HPLC and lyophilized to give the title compound(20 mg, 30%). LCMS (ESI): RT 4.13 min, [M+H]+ 467.2, method = B; lH NMR (400 MHz, DMSO-d6) δ 10.27 (s, 1H), 9.08 (t, J= 2.4 Hz, 1H), 8.70 (d, J= 0.5 Hz, 1H), 8.50 (s, 1H), 8.47 (d, J= 0.5 Hz, 1H), 8.37 (d, J= 5.9 Hz, 1H), 8.23 (s, 1H), 7.49 (s, 1H), 7.11 (s, 1H), 6.97 (d, J= 8.7 Hz, 1H), 6.63 (d, J= 8.8 Hz, 1H), 4.80 (m, 1H), 1.56 (d, J= 6.7 Hz, 6H), 1.40 - 1.31 (m, 2H), 1.30 - 1.23 (m, 2H).

References: [1]Patent: WO2014/81718,2014,A1 .Location in patent: Page/Page column 125.
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 9080 - 9093.

3
[ 269410-08-4 ]
[ 139631-62-2 ]
[ 1612172-62-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 5h;	To a solution of 4-pyrazoleboronic acid pinacol ester (1.02 g, 5.26 mmol) in DMF (15 mL) was added sodium hydride (60%, 0.32 g, 8 mmol) and cyclopropylsufonyl chloride (0.8 g, 5.78 mmol). The reaction was stirred at room temperature for 5 h. The mixture was then diluted with brine and extracted with EtOAc (3x). The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by flash chromatography on silica gel (solvent gradient: 0-100%) EtOAc in heptane) to give the title compound(0.8 g, 50%).
50%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 5h;	To a solution of 4-pyrazoleboronic acid pinacol ester (1.02 g, 5.26 mmol) in NN- dimethylformamide (15 mL) was added sodium hydride (60 wt% dispersion in mineral oil)(0.32 g, 8 mmol) and cyclopropylsufonyl chloride (0.8 g, 5.78 mmol). The reaction was stirred at room temperature for 5 h. The mixture was then diluted with brine and extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude material was purified via flash chromatography on silica gel (solvent gradient: 0%-100% EtOAc in heptane) to give l-(cyclopropylsulfonyl)-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (0.8 g, 50%).
49%		To a stirred solution of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH- pyrazole (1 g, 5.15 mmol) in DMF (15 mL) was added NaH (0.309 g, 7.73 mmol) and stirred for 5 min at room temperature. To the reaction mixture was addedcyclopropanesulfonyl chloride (0.797 g, 5.67 mmol) drop wise and stirred for 6 h at room temperature. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution (20 mL) and extracted with ethyl acetate (2x50 mL). The combined organic extracts were washed with water (50 mL) and saturated brine solution (2x50 mL). The organic layer was then dried over anhydrous sodium sulfate, filtered andconcentrated under reduced pressure. The crude material was purified by flash column chromatography (Combiflash, 24 g silica, 0-80% EtO Ac/PE) to afford 1- (cyclopropylsulfonyl)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (750 mg, 2.52 mmol, 49 % yield) as a white solid. NMR (400 MHz, DMSO-d6) d 8.36 (s, 1H), 8.30 (s, 1H), 3.17-0.00 (m, 1H), 1.31-1.25 (m, 14H), 1.21-1.17 (m, 2H).

22%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere;	Add 4- (4,4,5,5-tetramethyl-1,3,2-dioxolane-2-yl) -1H-pyrazole (3.0 g, 15 mmol), DMF (30 mL), NaH (0.62 g, 23 mmol) and cyclopropanesulfonyl chloride (2.4 g, 17 mmol) were replaced with nitrogen three times, and the reaction was stirred at room temperature for 24 h.Post-treatment: EA (50 mL) and water (50 mL) were added for dilution, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated by silica gel column chromatography (PE / EA (V / V) = 1/1) purification to give the title compound as a white solid (1.0 g, 3.4 mmol, 22%).
22%	In N,N-dimethyl-formamide; at 20℃; for 24h;	4- (4, 4, 5, 5-Tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-pyrazole (3.0 g, 15 mmol) , DMF (30 mL) , NaH (0.62 g, 23 mmol) and cyclopropanesulfonyl chloride (2.4 g, 17 mmol) were added to the single-necked bottle. The mixture was stirred at room temperature for 24 h, then diluted with EA (50 mL) and water (50 mL) . The organic phase was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EA (V/V) = 1/1) to give the title compound as a white solid (1.0 g, 3.4 mmol, 22%) . MS (ESI, pos. ion) m/z: 299.5 [M+H]+.
50 g		Under the protection of nitrogen and room temperature, pyrazole-4-boronic acid pinacol ester 8-1 (50g, 257.7mmol) was dissolved in tetrahydrofuran (800mL), and then,Add sodium hydride (60%, 15.5 g, 387.5 mmol) to the above reaction solution at 0 C. and continue stirring at this temperature for 30 minutes;Then, cyclopropanesulfonyl chloride (43.3 g, 308 mmol) was slowly added dropwise to the above reaction solution at 0 C; the reaction solution was raised to room temperature and stirring continued for 16 hours. After LCMS monitoring showed that the starting material disappeared, water (7 mL) was added to the reaction solution for quenching. The resulting mixture was filtered, and the filter cake was washed with ethyl acetate (50 mL×3 times). The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=10/1) to obtain 50 g of compound 8-2

References: [1]Patent: WO2014/81718,2014,A1 .Location in patent: Page/Page column 124; 125.
[2]Patent: WO2014/210354,2014,A1 .Location in patent: Page/Page column 39.
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 9080 - 9093.
[4]Patent: WO2020/168143,2020,A1 .Location in patent: Page/Page column 329; 330.
[5]Patent: CN110862390,2020,A .Location in patent: Paragraph 0448-0452.
[6]Patent: WO2020/43080,2020,A1 .Location in patent: Paragraph 00250.
[7]Patent: CN112538072,2021,A .Location in patent: Paragraph 0339-0344.

4
[ 1612172-62-9 ]
N-(2-(1-(cyclopropylsulfonyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)-1-isopropyl-3-(tetrahydrofuran-3-yloxy)-1H-pyrazolo[4,3-c]pyridin-6-amine [ No CAS ]