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[ CAS No. 402927-97-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 402927-97-3

Chemical Structure| 402927-97-3

Chemical Structure| 402927-97-3

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Quality Control of [ 402927-97-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 402927-97-3 ]

Product Details of [ 402927-97-3 ]

CAS No. :	402927-97-3	MDL No. :	MFCD06805736
Formula :	C₆H₁₄N₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FLQSRSQNICPZIH-UHFFFAOYSA-N
M.W :	178.25	Pubchem ID :	11355826
Synonyms :

Calculated chemistry of [ 402927-97-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.32
TPSA :	71.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.87
Log Po/w (XLOGP3) :	-0.87
Log Po/w (WLOGP) :	0.07
Log Po/w (MLOGP) :	-0.96
Log Po/w (SILICOS-IT) :	-0.92
Consensus Log Po/w :	-0.36

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.33
Solubility :	83.2 mg/ml ; 0.467 mol/l
Class :	Very soluble
Log S (Ali) :	-0.16
Solubility :	125.0 mg/ml ; 0.699 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.33
Solubility :	84.1 mg/ml ; 0.472 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.09

Safety of [ 402927-97-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 402927-97-3 ]

* 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 [ 402927-97-3 ]
Downstream synthetic route of [ 402927-97-3 ]

[ 402927-97-3 ] Synthesis Path-Upstream 1~3

1
[ 287953-38-2 ]
[ 402927-97-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With trifluoroacetic acid In dichloromethane at 20℃; for 16 h;	6.30 g (22.63 mmol) of (1-methanesulfonyl-piperidin-4-yl)-carbamic acid tert-butyl ester are dissolved in DCM (74 mL) and 17.4 mL (226 mmol) TFA are added. The reaction is stirred at RT for 16 h. The solvent is removed under reduced pressure. The crude product is diluted with diethylether at 40° C., the precipitate is filtered, washed with water and dried. The product is dissolved in MeOH, polymer supported hydrogencarbonate (PL-HCO₃ MP Resin, Agilent Technologies) is added and the suspension is stirred for a few minutes. The resin is filtered and the solvent is removed under reduced pressure to afford 4.00 g of 1-methanesulfonyl-piperidin-4-ylamine. Yield: 99percent; ESI-MS: 179 [M+H]⁺; HPLC (Rt): 0.26 min (method E)
99%	Stage #1: With trifluoroacetic acid In dichloromethane at 20℃; for 16 h;	6.30 g (22.63 mmol) of (1 -methanesulfonyl-piperidin-4-yl)-carbamic acid tert-butyl ester are dissolved in DCM (74 mL) and 17.4 mL (226 mmol) TFA are added. The reaction is stirred at RT for 16 h. The solvent is removed under reduced pressure. The crude product is diluted with diethylether at 40 °C, the precipitate is filtered, washed with water and dried. The product is dissolved in MeOH, polymer supported hydrogencarbonate (PL-HC0₃ MP Resin, Agilent Technologies) is added and the suspension is stirred for a few minutes. The resin is filtered and the solvent is removed under reduced pressure to afford 4.00 g of 1 -methanesulfonyl-piperidin- 4-ylamine. Yield: 99percent; ESI-MS: 179 [M+H]⁺; HPLC (Rt): 0.26 min (method E)
80%	With trifluoroacetic acid In dichloromethane at 20℃; for 1.5 h;	Intermediate 7: 1-(methylsulfonyl)piperidin-4-amine To a solution of tert-butyl (1-(methylsulfonyl)piperidin-4-yl)carbamate (2.72 g; 9.77 mmol) in DCM (30 mL) was added TFA (10.6 mL; 143 mmol). The mixture was stirred at r.t. for 1.5 hours and concentrated in vacuo. The residue was triturated with diethyl ether (30 mL), filtered, and washed with diethyl ether (30 mL). The solid was dissolved in H₂O (60 mL), basified with aqueous NaOH to pH=11, and extracted with DCM/i-PrOH (10/1, 60 mL*10). The combined organic layers were dried over anhydrous Na₂SO₄, filtered, and concentrated to afford 1.4 g (80percent) of the title compound as a yellow oil. LC-MS: m/z 179.0 [M+H]⁺. ¹H NMR (300 MHz, CDCl₃) δ [ppm]: 3.50-3.38 (m, 2H), 2.82 (s, 3H), 2.80-2.61 (m, 3H), 1.80-1.70 (m, 2H), 1.33-1.23 (m, 2H).

Reference： [1] Patent: US8865744, 2014, B1, . Location in patent: Page/Page column 26
[2] Patent: WO2014/184327, 2014, A1, . Location in patent: Page/Page column 27
[3] Patent: US2015/225367, 2015, A1, . Location in patent: Paragraph 0406
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6549 - 6560
[5] Bioorganic Chemistry, 2015, vol. 61, p. 21 - 27

2
[ 402927-96-2 ]
[ 402927-97-3 ]

Reference： [1] Patent: US2003/232847, 2003, A1, . Location in patent: Page 15

3
[ 73874-95-0 ]
[ 402927-97-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6549 - 6560
[2] Patent: WO2014/184327, 2014, A1,
[3] Bioorganic Chemistry, 2015, vol. 61, p. 21 - 27

[ 402927-97-3 ] Synthesis Path-Downstream 1~5

1
[ 402927-97-3 ]
[ 741713-37-1 ]
[ 741713-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (4-amino-2-ethylsulfanylpyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone With 3-chloro-benzenecarboperoxoic acid In chloroform at -15℃; for 1h; Stage #2: 4-amino-1-methanesulfonylpiperidine In isopropyl alcohol at 100 - 110℃; for 1h; microwave irradiation;

Reference： [1]Chu, Xin-Jie; DePinto, Wanda; Bartkovitz, David; So, Sung-Sau; Vu, Binh T.; Packman, Kathryn; Lukacs, Christine; Ding, Qingjie; Jiang, Nan; Wang, Ka; Goelzer, Petra; Yin, Xuefeng; Smith, Melissa A.; Higgins, Brian X.; Chen, Yingsi; Xiang, Qing; Moliterni, John; Kaplan, Gerald; Graves, Bradford; Lovey, Allen; Fotouhi, Nader [Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6549 - 6560]

2
[ 402927-97-3 ]
[ 23002-51-9 ]
(1-methanesulfonyl-piperidin4-yl)-(1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium hydrogencarbonate; In DMF (N,N-dimethyl-formamide); at 100℃; for 5h;	Example 19 Methanesulfonyl-piperidin-4-yl)-(1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine To a stirred solution of (1-methanesulfonyl-piperidin4-yl)-(1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine (Example 18, 61 mg, 0.40 mmol) in DMF (2.5 mL), sodium bicarbonate (60 mg) and 1-methanesulfonyl-piperidin-4-ylamine(85 mg, 0.48 mmol) were added and the mixture was stirred at 100 C. for 5 hours. The solvent was removed under reduced pressure and the residue was treated with water and the mixture was extracted with EtOAc. The extract was dried with sodium sulfate and concentrated to give a solid, which was purified by reverse phase HPLC to give an off-white solid. 29 mg, 29%. MS (M+H)+, 297.

Reference： [1]Patent: US2005/277655,2005,A1 .Location in patent: Page/Page column 16

3
[ 402927-97-3 ]
[ 71406-74-1 ]
[ 1620988-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	In 2-methoxy-ethanol; at 90℃;Inert atmosphere;	General procedure: A mixture of a 5-substituted-2,4-dichloropyrimidine 5 (1.0mmol), amino compound 6 (1.0mmol) and N,N-diisopropylethylamine (2.0mmol, 0.258g) in 8.0mL of dry 2-methoxyethanol was stirred at room temperature for about 12h under N2 flow. Then another amino compound 7 (1.1mmol) was added. The reaction mixture was heated at 90C for another 12-18h. After the reaction was complete according to the TLC detection, solvent was removed under reduced pressure and the residue was purified by column chromatography using a mixture of trichloromethane and methanol, (60:1) as an eluent to give the target compounds in yields of 58-84%.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 84,p. 127 - 134

4
[ 402927-97-3 ]
[ 86718-18-5 ]
C₁₅H₂₂N₄O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 2-ethoxy-4-amino-5-nitro-benzoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 20℃; for 1h; Stage #2: 4-amino-1-methanesulfonylpiperidine In dichloromethane at 20℃;	1 Example 1Preparation of a compound of formula I (R = methyl) with the following reaction formula: triethylamine, 100 mL of dichloromethane were added to the round bottom flask in turn.The temperature was lowered to 0 ° C, and 8 mL of ethyl chloroformate was slowly dropped into the reaction solution under stirring, and slowly added to room temperature for 1 h after the completion of the dropwise addition;Subsequently, 16 g of a dichloromethane solution of the compound of the formula III was dropped into the reaction liquid.After the completion of the dropwise addition, the reaction was carried out at room temperature, and the reaction was completely monitored by TLC.The reaction solution was slowly added dropwise to ice water and extracted with dichloromethane.The organic layer was washed with brine, dried and concentrated to give a white solid.Recrystallization gave 31 g of the compound of formula I in a yield: 91%; purity 98.8%.

Reference： [1]Current Patent Assignee: CHENGDU GIANTECH HI TECH DEVELOPMENT - CN109053552, 2018, A Location in patent: Paragraph 0040; 0041; 0042; 0043; 0050; 0051; 0052; 0053

5
[ 402927-97-3 ]
[ 13292-22-3 ]
C₄₄H₆₁N₃O₁₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: 3-Formyl-rifamycin SV (RAL)was purchased from LKT Laboratories Inc. (>98%). RAL (250.0mg, 0.34 mmol) was dissolved in 50 ml CH2Cl2 and afterthe addition of catalyst (0.025 mmol HCl/EtOH) respective mixtures wereprepared with each of the following compounds taken separately: 1-adamantylamine,1-methylpiperazine,1-(2-pyridyl)piperazine,1-(4-fluorobenzyl)piperazine,1-(2,4,6-trimethylbenzyl)piperazine, 1-bis(4-fluorophenyl)methylpiperazine, 1-(ethanesulfonyl)piperazine, 1-(methylsulfonyl)piperidin-4-amine, 4-(dimethylamino)-piperidine,1-(4-pyridyl)piperazine, 1-(2-pyrimidyl)piperazinedihydrochloride, 1,9-dimethyl-1,4,9-triazaspiro[5.5]undecanetrihydrochloride, 3,4-dihydro-2H-spiro[isoquinoline-1,4?-piperidine],n-piperidin-4-yl-methanesulfonamide,1-[3-(trifluoromethyl)pyrid-2-yl]piperazine,1-(cyclohexylmethyl)-4-piperidinamine,1,4?-bipiperidine-4-carboxylic acid dihydrochloride, (4-amino-1-piperidinyl)acetic acid dihydrochloride, 2-oxo-2-(1-piperidinyl)ethanamine,1-(2-amino-ethyl)-pyrrolidin-2-one,4-amino-1-Boc-piperidine, 3-amino-2-piperidinonehydrochloride, 1-acetyl-4-aminopiperidine hydrochloride in1 ml of CH3OH. Amines containinghydrochloride were neutralized with an equivalent amount of KOH/EtOH (0.06 mmolor 0.12 mmol or 0.18 mmol) solution. The mixtures were stirred at 40C for halfan hour and after that 3/4 of the solvent volume was distilled off. To thecooled reaction mixture (room temperature) the reductant NaBH3CN (13mg, 0.15 mmol) was added portionwise over 1 min. The reaction mixture wasstirred for one hour. Next the reaction mixture was evaporated to dryness,dissolved in 50 ml of CH2Cl2 and extracted twice with 50ml of water and brine (theses stages were omitted for reactions with1,4?-bipiperidine-4-carboxylic acid dihydrochloride,(4-amino-1-piperidinyl)acetic acid dihydrochloride). The separated organiclayer was evaporated and the synthesized derivatives of <strong>[13292-22-3]<strong>[13292-22-3]3-formylrifamycin</strong> SV</strong>(compounds 1-23) were next purified by column chromatography with silicagel (25 cm × 1 cm, silica gel 60, 0.040-0.063 mm/230-400 mesh ASTM, Fluka) withdichloromethane/methanol (from 200:1 to 3:1) as an eluent.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 167,p. 96 - 104

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Ghs Precautionary Statements

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P103	Read label before use
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Code	Phrase
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P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
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P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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Code	Phrase
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P378
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere