475105-35-2|(S)-tert-butyl 2-(aminomethyl)piperidine-1-carboxylate| Ambeed

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Quality Control of [ 475105-35-2 ] Purity: 95% SDS Specification

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Product Details of [ 475105-35-2 ]

CAS No. :	475105-35-2
Formula :	C₁₁H₂₂N₂O₂
M.W :	214.30
SMILES Code :	O=C(N1[C@H](CN)CCCC1)OC(C)(C)C
MDL No. :	MFCD06799358
InChI Key :	PTVRCUVHYMGECC-VIFPVBQESA-N
Pubchem ID :	1502020

Safety of [ 475105-35-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 475105-35-2 ] 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	1.0
Molar Refractivity	64.11
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.56 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.64
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	1.08
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.35
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	0.69
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.38

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.59
Solubility	5.57 mg/ml ; 0.026 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.	-1.84
Solubility	3.11 mg/ml ; 0.0145 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	-1.33
Solubility	10.1 mg/ml ; 0.0471 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.	-6.84 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)	2.68

Application In Synthesis of [ 475105-35-2 ]

* 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 [ 475105-35-2 ]

[ 475105-35-2 ] Synthesis Path-Downstream 1~21

1
[ 475105-35-2 ]
[ 143007-15-2 ]
[ 475105-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide); at 90℃; for 120.0h;	The amine D4 (0.607g), and 2-chloro-6, 7-difluoroquinoxaline McQuaid et. al. J. Med. Chem. (1992), 35 (18), 3319-24 (0.569g) were DISSOLVED IN DIMETHYLFORMAMIDE (LML) and heated to 90 C for 5 days under an atmosphere of argon. After cooling, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated brine, dried and evaporated. The residue was chromatographed over silica gel, eluting with a gradient of 10 to 50% ethyl acetate in hexane. The title compound was obtained as a pale yellow solid (0.460g), MHF 379. CLGH24F2N402 requires 378.
	In DMF (N,N-dimethyl-formamide); at 90℃; for 120.0h;	Description 7 : (S)-2-[(6, 7-DIFLUOROQUINOXALIN-2-YLAMINO) METHYL]-PIPERIDINE-1- carboxylic acid tert buty ester The amine D4 (0.607g), and 2-chloro-6, 7-difluoroquinoxaline McQuaid et. AL. J MED. Chem. (1992), 35 (18), 3319-24 (0.569g) were dissolved in dimethylformamide (LML) and heated to 90 C for 5 days under an atmosphere of argon. After cooling, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated brine, dried and evaporated. The residue was chromatographed over silica gel, eluting with a gradient of 10 to 50% ethyl acetate in hexane. The title compound was obtained as a pale yellow solid (0.460g), MET 379. CL9H24F2N402 requires 378.

References: [1]Patent: WO2004/41791,2004,A1 .Location in patent: Page 15.
[2]Patent: WO2004/41807,2004,A1 .Location in patent: Page 18.

2
[ 475105-34-1 ]
[ 475105-35-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol; for 16.0h;	The product from D3 (18. 2g) was dissolved in methanol (500ML) and treated with potassium carbonate (16. 1g). After stirring for 16h solvent was removed at reduced pressure and the residue partitioned between dichloromethane/water. The organic phase was separated, washed with brine, dried and solvent removed at reduced pressure. the residue was column chromatographed (silica gel, 0-10% (9: 1 methanol/ammonia) in dichloromethane eluant) to give the title compound (8.82g). Mass spectrum (APt : Found 215 (1W). CLLH22N202 requires 214. [A] D-32. 2&COMMAT; 28 c = 1% in chloroform. 1H NMR 8 : 1.20-1. 70 (8H, m), 1.46 (9H, s), 2.64-2. 80 (2H, m), 2.94 (1H, dd), 3.99 (1H, m) and 4.15 (1H, m).

References: [1]Patent: WO2004/41791,2004,A1 .Location in patent: Page 14-15.
[2]Patent: WO2004/41807,2004,A1 .Location in patent: Page 17.

3
[ 475105-35-2 ]
[ 549526-86-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18.0h;	Description 5 : (S)-2-(((1-BENZOFURAN-4-YL-METHANOYL)-AMINO)-METHYL)-PIPERIDINE-1- carboxylic acid tert-butyl ester To the amine from D4 (2.14g) in dichloromethane (50ML) was added BENZOFURAN-4- carboxylic acid (1.62g), followed by 1- (3-DIMETHYLAMINOPROPYL)-3-ETHYLCARBODIIMIDE hydrochloride (1.92g) and 1-HYDROXYBENZOTRIAZOLE hydrate (O. LG) and the mixture stirred at room temperature for 18H. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate solution. The organic phase was dried, evaporated and the residue chromatographed on silica gel eluting with a pentane/ethyl acetate gradient to afford the title product as a colurless solid (3g). Mass spectrum (API') : Found 381 (MNA+). C20H26N204 requires 358.

References: [1]Patent: WO2004/41807,2004,A1 .Location in patent: Page 17.

4
[ 475105-35-2 ]
[ 32779-36-5 ]
[ 475106-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; N-ethyl-N,N-diisopropylamine; In xylene; for 48.0h;Heating / reflux;	Description 13: (S)-2- [ (5-BROMO-PYRIMIDIN-2-YLAMINO)-METHYL]-PIPERIDINE-1- carboxylic acid tert butyl carbonate. The amine from D4 (lg), 5-bromo-2-chloropyrimidine (0.9g) were combined in XYLENE (20ML) containing potassium carbonate (1.29g) and diisopropylethylamine (2.43g) and warmed to reflux for 48h. The mixture was cooled to room temperature, filtered and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, pentane-25% ethyl acetate/pentane). The appropriate fractions were collected, solvent removed at reduced pressure to give the title compound (1.43g) as a colourless gum. Mass spectrum (APT) : Found 271 (&COMMAT;-TERT BOC). C15H23 79BRN402 requires 370.

References: [1]Patent: WO2004/41807,2004,A1 .Location in patent: Page 19.

5
[ 475105-35-2 ]
[ 77628-51-4 ]
[ 1040152-65-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 20.0h;	6-Methyl-imidazo[2,1-b]thiazole-5-carboxylic acid (2.0 g, 10.975 mmol) was dissolved in MeCN (35 mL), TBTU (3.52 g, 10.975 mmol) was added followed by the addition of DIPEA (2.82 mL, 16.462 mmol) and a solution of <strong>[475105-35-2](S)-2-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester</strong> (2.35 g, 10.975 mmol) in MeCN (20 mL). Stirring at rt was continued for 20 h. The reaction mixture was concentrated under reduced pressure, again diluted with EtOAc and subsequently washed with a sat. citric acid solution, a sat. NaHCO3 solution and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give 3.98 g (95%) of (S)-2-[(6-methyl-imidazo[2,1-b]thiazole-5-carbonyl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester as a slightly orange foam which was used without further purification. LC-MS: tR=0.80 min; [M+H]+=379.46.
95%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 20.0h;	STEP 1:6-Methyl-imidazo[2,l-b]thiazole-5-carboxylic acid (2.0 g, 10.975 mmol) was dissolved in MeCN (35 mL), TBTU (3.52 g, 10.975 mmol) was added followed by the addition of DIPEA (2.82 mL, 16.462 mmol) and a solution of (S)-2-aminomethyl-piperidine-l- carboxylic acid tert-butyl ester (2.35 g, 10.975 mmol) in MeCN (20 mL). Stirring at rt was continued for 20 h. The reaction mixture was concentrated under reduced pressure, again diluted with EtOAc and subsequently washed with a sat. citric acid solution, a sat. NaHCO3 solution and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give 3.98 g (95%) of (S)-2-[(6-methyl- imidazo[2, 1 -b]thiazole-5-carbonyl)-amino]-methyl} -piperidine- 1 -carboxylic acid tert- butyl ester as a slightly orange foam which was used without further purification. LC- MS: tR = 0.80 min; [M+H]+ = 379.46.

References: [1]Patent: US2010/222328,2010,A1 .Location in patent: Page/Page column 32-33.
[2]Patent: WO2008/139416,2008,A1 .Location in patent: Page/Page column 66.

6
[ 475105-35-2 ]
[ 1609082-37-2 ]
[ 1609341-89-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	Example 172 8-[(2,6-Difluorobenzyl)oxy]-2,6-dimethyl-N-[(2S)-piperidin-2-ylmethyl]imidazo[1,2-a]pyridine-3-carboxamide At RT, 53 mg (0.25 mmol, 1.1 equivalents) of <strong>[475105-35-2]tert-butyl (2S)-2-(aminomethyl)piperidin-1-carboxylate</strong> were added to 75 mg of 8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]-pyridine-3-carboxylic acid (Example 21A, 0.23 mmol, 1 equivalent), 90 mg of O-(7-azabenzotriazol-1-yl)-N,N,N'N'-tetramethyluronium hexafluorophosphate (HATU, 0.24 mmol, 1.05 equivalents) and 88 mg of N,N-diisopropylethylamine (0.12 ml, 0.68 mmol, 3 equivalents) in 1.4 ml of DMF, and the mixture was stirred at RT overnight. After the reaction had ended, the mixture was purified by preparative HPLC (method: RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The product fractions obtained were dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried over sodium sulphate, filtered, concentrated and lyophilized. This gave 66 mg (64% of theory; purity 95%) of the title compound. LC-MS (Method 2): Rt=0.65 min MS (ESpos): m/z=429.3 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=0.99-1.14 (m, 1H), 1.21-1.36 (m, 2H), 1.45-1.54 (m, 1H), 1.59-1.66 (m, 1H), 1.70-1.77 (m, 1H), 2.31 (s, 3H), 2.60-2.69 (m, 1H), 2.92-2.98 (m, 1H), 3.16-3.29 (m, 2H), 5.28 (s, 2H), 6.91 (s, 1H), 7.24 (t, 2H), 7.55-7.64 (m, 1H), 7.74 (t, 1H), 8.46 (s, 1H), [further signal hidden under solvent peaks].

References: [1]Patent: US2014/128372,2014,A1 .Location in patent: Paragraph 1646; 1647; 1648; 1649; 1650.

7
[ 475105-35-2 ]
[ 1246616-66-9 ]
C₂₇H₃₄N₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	In toluene; at 100℃; for 5h;	Compound 1 (7.43g, 23.3mmol) and Compound 2 (5.00g, 23.3mmol) were added to toluene (75ml). The mixturewas stirred at 100C for 5 hours. After the reaction mixture was cooled to room temperature, the solvent was removedin vacuo. The obtained crude was purified by silica-gel column chromatography and eluted with n-hexaneethyl acetateto give Compound 3 (7.78g, 65%).MS: m/z = 515 [M+H]+

References: [1]Patent: EP3196201,2017,A1 .Location in patent: Paragraph 0224; 0225.

8
[ 475105-35-2 ]
C₂₁H₂₂N₂O₅ [ No CAS ]

References: [1]Patent: EP3196201,2017,A1 .

9
[ 475105-35-2 ]
C₂₀H₂₀N₂O₅ [ No CAS ]

References: [1]Patent: EP3196201,2017,A1 .

10
[ 475105-35-2 ]
[ 1083283-39-9 ]

References: [1]Patent: WO2008/139416,2008,A1 .

11
[ 475105-35-2 ]
(S)-6-methyl-imidazo[2,1-b]thiazole-5-carboxylic acid [1-(2-cyclopropyl-5-p-tolyl-thiazole-4-carbonyl)-piperidin-2-ylmethyl]-amide [ No CAS ]

References: [1]Patent: WO2008/139416,2008,A1 .

12
[ 475105-35-2 ]
[ 7693-46-1 ]
tert-butyl (2S)-2-[[(4-nitrophenoxycarbonyl)amino]methyl]piperidine-1-carboxylate [ No CAS ]