[ CAS No. 1239320-11-6 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 1239320-11-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1239320-11-6 ]

Product Details of [ 1239320-11-6 ]

CAS No. :	1239320-11-6	MDL No. :	MFCD29085851
Formula :	C₁₂H₂₁NO₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PVWNPIKNKQATNC-UHFFFAOYSA-N
M.W :	291.36	Pubchem ID :	86730907
Synonyms :

Safety of [ 1239320-11-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1239320-11-6 ]

* 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.

Upstream synthesis route of [ 1239320-11-6 ]
Downstream synthetic route of [ 1239320-11-6 ]

[ 1239320-11-6 ] Synthesis Path-Upstream 1~1

1
[ 1239320-11-6 ]
[ 1211586-09-2 ]

Reference： [1] Patent: WO2016/90079, 2016, A1,

[ 1239320-11-6 ] Synthesis Path-Downstream 1~6

1
[ 1147557-97-8 ]
[ 124-63-0 ]
[ 1239320-11-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 0 - 20℃;	Compound 1 (5.0 g, 23.4 mmol) and triethylamine (2.9 g, 28.1 mmol) were dissolved in dichloromethane (50 mL)And then methanesulfonyl chloride (3.22 g, 28.13 mmol) was added dropwise at 0 C,Stir overnight at room temperature.TLC (petroleum ether / ethyl acetate volume ratio = 1/1, Rf = 0.5) showed completion of the reaction.The reaction solution was quenched with water, and the organic phase was washed with saturated ammonium chloride solution and dried to dryness to give Compound 2 (6.6 g) in a yield of 100%.
100%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a solution of ferf -butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (2 g , 9.4 mmol) in dichloromethane (25 mL) was added triethylamine (2.6 mL, 18.8 mmol). The solution was cooled to o C and a solution of methanesulfonylchloride (0.8 mL, 10.3 mmol) in dichloromethane (5 mL) was added dropwise. The mixture was stirred for 18 hours at room temperature and then washed with water and brine, dried (sodium sulfate), filtered and evaporated to afford the title compound (2.7 g, yield 100 %) as a white solid. (0905) NMR (CDC13): delta = 4.89 (m, 1 H), 3-94 (s, 4 H), 2.99 (s, 3 H), 2.70 (m, 2 H), 2.48 (m, 2 H) and 1.44 (s, 9 H).
99%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 20h;	Step 9 tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2- carboxylate [00182] ferf-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (505 mg, 2.37 mmol) was dissolved in DCM (6.0 mL). The solution was cooled to 0 C with an external ice-bath. Et3N (330 pL, 2.37 mmol) and DMAP (3.0 mg, 0.0237 mmol) were added. Methanesulfonyl chloride (184 pL, 2.37 mmol) was then added dropwise by syringe. The solution was stirred at 0 C for 2.0 hrs, was then allowed to warm to room temperature and stirred at room temperature for 18 hrs. A saturated solution of NH4CI (20 mL) was added and stirred at room temperature for 10 min. The layers were separated. The aqueous phase was extracted with DCM (3x30 mL). The combined organic phase was dried over anhydrous Na2SO4, concentrated by evaporation in vacuo to afford terf-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate (684 mg, 99%) as a white solid. [00183] 1HNMR (300 MHz, CDCI3): delta 4.89 (m, 1 H), 3.93 (s, 4 H), 2.99 (s, 3 H), 2.68 (m, 1 H), 2.48 (m, 2 H), 1.43 (s, 9 H).

73.2%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a stirred solution of <strong>[1147557-97-8]tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate</strong> 23-1 (500 mg, 2.34 mmol) in dichloromethane (10 mL) at 0C was added triethylamine (474.46 mg, 4.69 mmol, 653.53 uL) followed by rnesyl chloride (402.83 mg, 3.52 mmol, 272.18 uL) drop wise. The reaction mixture was allowed to stir at ambient temperature for 1 hour. The reaction mass was then diluted with DCM and washed with water, a saturated solution of NaHCO3 and brine. The organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to afford crude product that was triturated with diethyl ether to afford tert-butyl 6- methylsulfonyloxy-2-azaspiro[3.3]heptane-2-carboxylate 23-2 (500 mg, 1.72 mmol, 73 20% yield) as white semisolid. NMR (d6-DMSO, 400 MHZ) d 4.89-4.85 (m, 1H), 3.85-3.81 (m, 4H), 3.13 (s, 3H), 2.63-2.60 (m, 2H), 2.37-2.34 (m, 2H), 1.35 (s, 9H),
	With triethylamine; In dichloromethane; at 0℃; for 2h;	To a solution of <strong>[1147557-97-8]tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate</strong> (26.1) (500 mg, 2.34 mmol) and TEA (472 mg, 4.68 mmol) in DCM (5 mL) was added MsCl (322 mg, 2.81 mmol) dropwise at 0 C. The resulting mixture was stirred at 0 C for 2 h. TLC showed complete reaction. The mixture was poured into water and extracted with DCM. The organic phase was washed with water and brine, dried over Na2SO4 and concentrated to afford tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate (26.2) (700 mg, crude), which was used in next step without further purification.
40.7 g	With triethylamine; In tetrahydrofuran; at 0 - 0.35℃; for 2h;Inert atmosphere;	To a solution of <strong>[1147557-97-8]tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate</strong> (30.0 g) and triethylamine (29.2 mL) in THF (600 mL) was added methanesulfonyl chloride (13.0 mL) at 0 C. The mixture was stirred at room temperature under nitrogen atmosphere for 2 hr. The mixture was quenched with water at 0 C. and extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (40.7 g). 1H NMR (300 MHz, CDCl3) 51.43 (9H, s), 2.39-2.55 (2H, m), 2.61-2.76 (2H, m), 2.98 (3H, s), 3.93 (4H, s) 4.89 (1H, quin, J=7.18 Hz).
	With triethylamine; In dichloromethane; at 20℃; for 3.25h;	To a solution of <strong>[1147557-97-8]tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate</strong> (2.0 g, 9.38 mmol) in DCM (45 mL) at room temperature was added Et3N (3.27 mL, 23.4 mmol) and MsCl (1.1 mL, 14.1 mmol) sequentially. After 3.25 hours, the reaction was quenched by the addition of water and DCM. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layer was dried over sodium sulfate, filtered, and concentrated to afford crude material considered to be quantitative of tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate (9.38 mmol, 100% yield).
	With dmap; triethylamine; In dichloromethane; at 0℃; for 3h;	Commercially available /ert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (250 mg, 1.0 equiv), TEA (360 mg, 3.0 equiv) and DMAP (10 mg) were combined in DCM (25 mL) at 0C. MsCl (162 mg, 1.2 equiv) was added dropwise. The mixture was stirred at 0C for 3h. The reaction mixture was diluted with DCM (30 mL) and then washed with 1N HC1, water, and brine to afford /ert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate (324 mg, yield 95%) which was used without further purification.

Reference： [1]Patent: CN105646318,2016,A .Location in patent: Paragraph 0007
[2]Patent: WO2019/8025,2019,A1 .Location in patent: Page/Page column 141
[3]Patent: WO2013/13308,2013,A1 .Location in patent: Paragraph 00181-00183
[4]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 397 - 402
[5]Patent: WO2019/191112,2019,A1 .Location in patent: Page/Page column 323; 324
[6]Patent: WO2016/90079,2016,A1 .Location in patent: Paragraph 00489
[7]Patent: US2018/280389,2018,A1 .Location in patent: Paragraph 3468; 3629; 3630
[8]Patent: US2019/185469,2019,A1 .Location in patent: Paragraph 0825-0826
[9]Patent: WO2019/177997,2019,A1 .Location in patent: Paragraph 00251

2
[ 1181816-12-5 ]
[ 1239320-11-6 ]

Reference： [1]Patent: WO2013/13308,2013,A1

3
[ 1239320-11-6 ]
[ 1211586-09-2 ]

Reference： [1]Patent: WO2016/90079,2016,A1

4
[ 1239320-11-6 ]
[ 35344-95-7 ]
tert-butyl 6-(3-formylpyrazol-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.01%	With caesium carbonate; In N,N-dimethyl-formamide; for 16h;Heating;	To a stirred solution of tert-butyl 6-methylsulfonyloxy-2-azaspiro[3.3]heptane-2- carboxylate 23-2 (500 mg, 1.72 mmol) and lH-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> 23-3 (164.89 mg, 1.72 mmol) inDMF (10 mL) was added cesium carbonate (1.12 g, 3.43 mmol) and the reaction mixture was stirred at 80C for 16 hours. The reaction mixture was diluted with cold water and EtOAc, and the layers were separated. The organic layer was washed with water, brine, dried over NaiiSCfi and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford tert-butyl 6-(3-formylpyrazol-l-yl)-2-azaspiro[3.3]heptane-2- carboxylate 23-4 (420 mg, 1.44 mmol, 84.01% yield) as gummy solid. LC MS: ES+ 292.2.

Reference： [1]Patent: WO2019/191112,2019,A1 .Location in patent: Page/Page column 322; 323

5
[ 1239320-11-6 ]
[ 175277-99-3 ]
[ 2428639-79-4 ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;	Step a) tert-butyl 6-((2-chloro-4-fluorophenyl)sulfonyl)-2-azaspiro[3.3Jheptane-2-carboxylate In a 20ml glas tube, tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate (538 mg, 1.84 mmol), 2-chloro-4-fluorobenzenethiol (250mg, 1.54 mmol) and K2CO3 (425 mg, 3.07 mmol) were dissolved in DMF (7 ml) under argon atmosphere. The suspension was heated-up at 80°C for 4hr. The reaction mixture was diluted with ethyl acetate (20 ml), washed twice with water (40 ml), then with brine(40 ml). The organic layer was dried over MgSO i, filter off and the solvent was removed under reduced pressure. The crude was purified over 50g silica with heptane / EA 0 to 40% in 40min, after removing the solvent under vacuum the product was obtained as a colorless viscous oil (218 mg, 38%). MS (ESI): m/z = 302.1 [M-56+H]+.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2020/104494, 2020, A1 Location in patent: Page/Page column 133; 134

6
[ 1239320-11-6 ]
[ 1824024-00-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: Caswell No_. 744A / N,N-dimethyl-formamide / 24 h / 70 °C 2.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C 3.1: Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene / 3 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 4.2: 1 h / 20 °C 5.1: hydrogen; palladium 10% on activated carbon / ethanol

Reference： [1]Current Patent Assignee: 1CBIO - WO2022/91048, 2022, A1

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[ CAS No. 1239320-11-6 ] {[proInfo.proName]}

Quality Control of [ 1239320-11-6 ]

Related Doc. of [ 1239320-11-6 ]

Product Details of [ 1239320-11-6 ]

Safety of [ 1239320-11-6 ]

Application In Synthesis of [ 1239320-11-6 ]

[ 1239320-11-6 ] Synthesis Path-Upstream 1~1

[ 1239320-11-6 ] Synthesis Path-Downstream 1~6

Precautionary Statements-General

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