169750-96-3|tert-Butyl (3-methylpiperidin-3-yl)carbamate| Ambeed

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Quality Control of [ 169750-96-3 ] Purity: 95% SDS Specification

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Product Details of [ 169750-96-3 ]

CAS No. :	169750-96-3
Formula :	C₁₁H₂₂N₂O₂
M.W :	214.30
SMILES Code :	O=C(OC(C)(C)C)NC1(C)CNCCC1
MDL No. :	MFCD13194151
InChI Key :	IKLFTJQKKCELGD-UHFFFAOYSA-N
Pubchem ID :	19691473

Safety of [ 169750-96-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 169750-96-3 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	50.36 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.59
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.24
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.27
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.15
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.31
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.51

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.69
Solubility	4.42 mg/ml ; 0.0206 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.9
Solubility	2.73 mg/ml ; 0.0127 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.65
Solubility	0.475 mg/ml ; 0.00222 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.73 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.79

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.

Downstream synthetic route of [ 169750-96-3 ]

[ 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)+.

References: [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)+.

References: [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.

References: [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.

References: [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.

References: [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.

References: [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.

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

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