[ CAS No. 169750-96-3 ] {[proInfo.proName]}

Name: 169750-96-3|tert-Butyl (3-methylpiperidin-3-yl)carbamate|95%
Brand: Ambeed
SKU: A113069
Rating: 96 (32 reviews)

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Quality Control of [ 169750-96-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 169750-96-3 ]

SDS Specification

Alternatived Products of [ 169750-96-3 ]

Product Details of [ 169750-96-3 ]

CAS No. :	169750-96-3	MDL No. :	MFCD13194151
Formula :	C₁₁H₂₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IKLFTJQKKCELGD-UHFFFAOYSA-N
M.W :	214.30	Pubchem ID :	19691473
Synonyms :

Calculated chemistry of [ 169750-96-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	64.15
TPSA :	50.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.59
Log Po/w (XLOGP3) :	1.24
Log Po/w (WLOGP) :	1.27
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	1.31
Consensus Log Po/w :	1.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.69
Solubility :	4.42 mg/ml ; 0.0206 mol/l
Class :	Very soluble
Log S (Ali) :	-1.9
Solubility :	2.73 mg/ml ; 0.0127 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.65
Solubility :	0.475 mg/ml ; 0.00222 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.79

Safety of [ 169750-96-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 169750-96-3 ]

* 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 [ 169750-96-3 ]
Downstream synthetic route of [ 169750-96-3 ]

[ 169750-96-3 ] Synthesis Path-Upstream 1~5

1
[ 1196506-86-1 ]
[ 169750-96-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogen In ethanol at 220℃; for 2 h; Inert atmosphere	A solution of rac-benzyl 3- ((?er?-butoxycarbonyl)amino)-3-methylpiperidine-l-carboxylate (78 mg, 0.22 mmol, made as described in WO09/140320) in EtOH (5 mL) was degassed by bubbling N₂ (g) through the solution for 10 min. Pd/C (10 wt.percent, 24 mg, 0.022 mmol) was added. A gas bag with a 3-way stopcock filled with H₂ was attached to the flask. The flask was evacuated under vacuum and then back-filled with H₂ (3X). The mixture was stirred for 2 h at RT. The solution was degassed by bubbling N₂ (g) through the solution for 10 min and filtered through Celite. The solution was concentrated to afford rac-tert-butyl (3- methylpiperidin-3-yl)carbamate (42 mg, 0.20 mmol, 88 percent yield) as a clear, colorless oil. MS (ESI, pos. ion) m/z: 215.1 (M+l).
72%	With hydrogen In methanol for 1 h;	[00252] Step E: Benzyl 3-(tert-butoxycarbonylamino)-3-methylpiperidine-l-carboxylate(1.4 g, 4.0 mmol) and 10percent Pd/C (0.21 g, 0.2 mmol) in MeOH (20 mL) were stirred under H₂ atmosphere (1 atm) for 1 hour. The catalyst was removed by filtration and washed with methanol. The filtrate was concentrated to give tert-butyl 3-methylpiperidin-3-ylcarbamate (0.62 g, 72percent yield) as a solid.

Reference： [1] Patent: WO2012/148775, 2012, A1, . Location in patent: Page/Page column 124; 125
[2] Patent: WO2009/140320, 2009, A1, . Location in patent: Page/Page column 73

2
[ 310454-53-6 ]
[ 169750-96-3 ]

Reference： [1] Patent: WO2009/140320, 2009, A1,

3
[ 664364-60-7 ]
[ 169750-96-3 ]

Reference： [1] Patent: WO2009/140320, 2009, A1,

4
[ 174543-78-3 ]
[ 169750-96-3 ]

Reference： [1] Patent: WO2009/140320, 2009, A1,

5
[ 71962-74-8 ]
[ 169750-96-3 ]

Reference： [1] Patent: WO2009/140320, 2009, A1,

[ 169750-96-3 ] Synthesis Path-Downstream 1~13

1
[ 1172068-39-1 ]
[ 169750-96-3 ]
C₂₄H₂₉BrN₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 143℃; for 24h;	[00507] N-(5-Bromo-4-fluoro-lH-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (100 mg, 0.298 mmol), <strong>[169750-96-3]tert-butyl 3-methylpiperidin-3-ylcarbamate</strong> (192 mg, 0.895 mmol) and DIEA (0.052 mL, 0.298 mmol) in n-BuOH (3 mL) were stirred at 143C (bath) for 24 hours. The solvent was removed, and the residue was dissolved in ethyl acetate (20 mL), washed with water (10 mL), brine (10 mL), dried (sodium sulfate), and concentrated in vacuo. The residue obtained was purified by C- 18 reverse phase flash chromatography (Biotage SP4 unit, C-18 25M+ column, 10- 80% CH3CN/water gradient; 30 CV). The product isolated was dissolved in DCM (2 mL), andTFA (0.5 mL) was added. The mixture was stirred at room temperature for 1 hour. The solvent was then removed. The residue was dissolved in DCM (1 mL), and 2N HCl in ether (3 mL) was added. The solid formed was collected by filtration to give N-(4-(3 -amino-3 -methylpiperidin- 1- yl)-5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide hydrochloride (12.8 mg, 7.96% yield) <n="165"/>as a solid. 1H NMR (400 MHz, (CD3)2SO) delta 12.09 (s, IH), 10.54 (s, IH), 9.37 (s, IH), 8.91 (d,IH), 8.70 (m, IH), 8.29 (s, IH), 8.05 (s, 3H), 7.83 (m, IH), 7.54 (s, IH), 3.40 (m, 2H), 3.27 (m, IH), 3.17 (m, 2H), 1.65 (m, 2H), 1.46 (m, IH), 2.00 (s, 3H); LCMS (APCI+) m/z 429 (M+H)+.

Reference： [1]Patent: WO2009/140320,2009,A1 .Location in patent: Page/Page column 163-164

2
[ 169750-96-3 ]
[ 1196507-71-7 ]
C₂₄H₂₉FN₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 150℃; for 24h;	00508] A mixture of N-(4,5-difluoro-lH-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (50 mg,0.18 mmol; Example 13, Step D), <strong>[169750-96-3]tert-butyl 3-methylpiperidin-3-ylcarbamate</strong> (78 mg, 0.37 mmol, Example C) and DIEA (0.032 mL, 0.182 mmol) in n-BuOH (1 mL) was stirred at 150C (bath) for 24 hours in a sealed tube. The solvent was removed, and the resulting residue was dissolved in ethyl acetate (20 mL), washed with water (10 mL), brine (10 mL), dried (sodium sulfate) and concentrated in vacuo. The residue obtained was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit, C- 18 25M column, 10-80% CH3CN/water gradient; 30CV). The product isolated was dissolved in DCM (2 mL), and TFA (0.5 mL) was added. The mixture was stirred at room temperature for 1 hour. The solvent was removed. The residue was dissolved in MeOH (1 mL), and 2N HCl in ether (3 mL) was added. The solid formed was collected by filtration to give N-(4-(3-amino-3-methylpiperidin-l-yl)-5-fluoro-lH-pyrrolo[2,3- b]pyridin-3-yl)nicotinamide hydrochloride (0.050 g, 56%) as a solid. 1H NMR (400 MHz, (CD3)2SO) delta 12.04 (s, IH), 11.03 (s, IH), 9.49 (s, IH), 8.95 (m, 2H), 8.27 (s, 2H), 8.18 (d, IH),7.93 (m, IH), 7.53 (d, IH), 3.43 (m, IH),. 3.36 (m, 2H), 3.04 (m, IH), 1.71 (m, IH), 1.51 (m, 2H), 1.31 (m, IH), 1.22 (s, 3H). LCMS (APCI+) m/z 369(M+H)+.

Reference： [1]Patent: WO2009/140320,2009,A1 .Location in patent: Page/Page column 164

3
[ 1196506-86-1 ]
[ 169750-96-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 220℃; for 2h;Inert atmosphere;	A solution of rac-benzyl 3- ((?er?-butoxycarbonyl)amino)-3-methylpiperidine-l-carboxylate (78 mg, 0.22 mmol, made as described in WO09/140320) in EtOH (5 mL) was degassed by bubbling N2 (g) through the solution for 10 min. Pd/C (10 wt.%, 24 mg, 0.022 mmol) was added. A gas bag with a 3-way stopcock filled with H2 was attached to the flask. The flask was evacuated under vacuum and then back-filled with H2 (3X). The mixture was stirred for 2 h at RT. The solution was degassed by bubbling N2 (g) through the solution for 10 min and filtered through Celite. The solution was concentrated to afford rac-tert-butyl (3- methylpiperidin-3-yl)carbamate (42 mg, 0.20 mmol, 88 % yield) as a clear, colorless oil. MS (ESI, pos. ion) m/z: 215.1 (M+l).
72%	With hydrogen;palladium 10% on activated carbon; In methanol; under 760.051 Torr; for 1h;	[00252] Step E: Benzyl 3-(tert-butoxycarbonylamino)-3-methylpiperidine-l-carboxylate(1.4 g, 4.0 mmol) and 10% Pd/C (0.21 g, 0.2 mmol) in MeOH (20 mL) were stirred under H2 atmosphere (1 atm) for 1 hour. The catalyst was removed by filtration and washed with methanol. The filtrate was concentrated to give tert-butyl 3-methylpiperidin-3-ylcarbamate (0.62 g, 72% yield) as a solid.

Reference： [1]Patent: WO2012/148775,2012,A1 .Location in patent: Page/Page column 124; 125
[2]Patent: WO2009/140320,2009,A1 .Location in patent: Page/Page column 73

4
[ 169750-96-3 ]
[ 1620011-38-2 ]
[ 1620013-22-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In isopropyl alcohol; at 100℃; for 0.333333h;	A mixture of 4-chloro-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (200 mg, 1.01 mmol), <strong>[169750-96-3]tert-butyl (3-methylpiperidin-3-yl)carbamate</strong> (227 mg, 1.06 mmol) and triethylamine (281 muL, 2.01 mmol) in isopropyl alcohol (1.2 mL) was stirred at 100 C. for 20 min. After cooling, the sub-title compound precipitated out and was collected by vacuum filtration, followed by washing with cold ether to give the sub-title compound as light yellow powder. LCMS calc. for C19H29N4O4 (M+H)+: m/z=377.2. Found: 377.2.

Reference： [1]Patent: US2014/200227,2014,A1 .Location in patent: Paragraph 0989; 0990

5
[ 169750-96-3 ]
6-(3-fluoro-5-isobutoxy-phenyl)-2-(2,2,4-trimethylpyrrolidin-1-yl)pyridine-3-carboxylic acid [ No CAS ]
tert-butyl N-[1-[[6-(3-fluoro-5-isobutoxy-phenyl)-2-(2,2,4-trimethylpyrrolidin-1-yl)pyridine-3-carbonyl]sulfamoyl]-3-methyl-3-piperidyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		A solution of 6-(3-fluoro-5-isobutoxy-phenyl)-2-(2,2,4-trimethylpyrrolidin-1-yl)pyridine-3-carboxylic acid (40.45 mg, 0.1000 mmol) and chlorosulfonyl isocyanate (16.98 mg, 10.44 muL, 0.1200 mmol) in dichloromethane (1.000 mL) was stirred for 45 minutes. Triethylamine (15.18 mg, 20.91 muL, 0.1500 mmol) and <strong>[169750-96-3]tert-butyl-N-(3-methyl-3-piperidyl)carbamate</strong> (32.15 mg, 0.1500 mmol) were added, and the reaction was stirred for three days. The reaction was purified by silica gel chromatography with 0-5% methanol in dichloromethane to give tert-butyl (1-(N-(6-(3-fluoro-5-isobutoxyphenyl)-2-(2,2,4-trimethylpyrrolidin-1-yl)nicotinoyl)sulfamoyl)-3-methylpiperidin-3-yl)carbamate (34 mg, 0.050 mmol, 50.%) as a colorless solid.

Reference： [1]Patent: US2016/95858,2016,A1 .Location in patent: Paragraph 4672; 4673

6
[ 169750-96-3 ]
4-[4-(2-tert-butyl-4-pyridyl)-2-thienyl]-3-chlorobenzoic acid [ No CAS ]
tert-butyl N-[1-[4-[4-(2-tert-butyl-4-pyridyl)-2-thienyl]-3-chlorobenzoyl]-3-methyl-3-piperidyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
300 mg		To a solution of 4-[4-(2-tert-butyl-4-pyridyl)-2-thienyl]-3-chloro-benzoic acid (300 mg, 0.8086 mmol) in DMF (10 mL), was added DIPEA (418 mg, 3.2344 mmol), followed by the addition of HATU (615 mg, 1.6172 mmol). The reaction mixture was stirred for 30 min at RT. tert-Butyl N-(3-methyl-3-piperidyl)carbamate (433 mg, 2.022 mmol) was added and the reaction mixture stirred for 16 h at RT. The reaction was monitored by TLC and LCMS. On completion, the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2100 mL). The combined organic layer was washed with water (250 mL) and brine (2*50 mL) and dried over anhydrous sodium sulfate to obtain 500 mg of crude product. The crude compound was purified by reverse phase combi-flash to afford tert-butyl N-[1-[4-[4-(2-tert-butyl-4-pyridyl)-2-thienyl]-3-chloro-benzoyl]-3-methyl-3-piperidyl]carbamate (300 mg) as a white solid.

Reference： [1]Patent: US2018/51013,2018,A1 .Location in patent: Paragraph 0865; 0866

7
[ 50-00-0 ]
[ 169750-96-3 ]
1,3-dimethylpiperidin-3-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of tert-butyl (3-methylpiperidin-3-yl) carbamate (50. mg, 0.23 mmol), paraformaldehyde (35 mg, 1.2 mmol), and sodium triacetoxyborohydride (84 mg, 0.40 mmol) in DCE (1.0 mL) was stirred at ambient temperature overnight. 4 N HCl in 1,4-dioxane (1 mL) was added and the resultant solution was stirred at ambient temperature for 5 h. The volatiles were removed in-vacuo and the residue was azeotropically washed with acetonitrile prior to placing it under high vacuum. The crude product was used in the subsequent reaction without further purification. LCMS for C7H16N2 (M+H)+: calculated m/z=129.2; found 129.1.

Reference： [1]Patent: US2018/9816,2018,A1 .Location in patent: Paragraph 1583

8
[ 310454-53-6 ]
[ 169750-96-3 ]