[ CAS No. 741687-07-0 ]

Name: 741687-07-0|tert-Butyl 4-amino-4-ethylpiperidine-1-carboxylate|96%
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Quality Control of [ 741687-07-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 741687-07-0 ]

Product Details of [ 741687-07-0 ]

CAS No. :	741687-07-0	MDL No. :	MFCD12408566
Formula :	C₁₂H₂₄N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GJKGQHBSAKUVNM-UHFFFAOYSA-N
M.W :	228.33 g/mol	Pubchem ID :	45095672
Synonyms :

Calculated chemistry of [ 741687-07-0 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.92
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	68.95
TPSA :	55.56 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) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.87
Log Po/w (XLOGP3) :	1.44
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.44
Log Po/w (SILICOS-IT) :	1.19
Consensus Log Po/w :	1.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.9
Solubility :	2.88 mg/ml ; 0.0126 mol/l
Class :	Very soluble
Log S (Ali) :	-2.21
Solubility :	1.4 mg/ml ; 0.00613 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.93
Solubility :	2.66 mg/ml ; 0.0117 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.33

Safety of [ 741687-07-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 741687-07-0 ]

* 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 [ 741687-07-0 ]

[ 741687-07-0 ] Synthesis Path-Downstream 1~18

1
4-ethyl-4-isocyanato-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
[ 741687-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium trimethylsilonate; In tetrahydrofuran; at 18 - 25℃; for 18h;	Step B. To a solution of the above solid from step A (3.28g) in THF (50ml) was addedpotassium trimethylsilanolate (3.68g) and the resulting mixture was stirred at roomtemperature for 18 hours. The reaction mixture was partitioned between dichloromethane andsaturated sodium bicarbonate. The organic extracts were dried (MgSO4) and evaporated todryness to give the sub-title compound (2.42g) as an orange oil which was used withoutfurther purification. NMR(d6 DMSO): 0.75 (t, 3H), 1.1-1.4 (m, 6H), 1.3 (s, 9H), 3.1 (m, 2H),3.45(m,2H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3675 - 3678
[2]Patent: WO2006/1752,2006,A1 .Location in patent: Page/Page column 81

2
[ 124443-68-1 ]
[ 741687-07-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3675 - 3678

3
[ 578021-55-3 ]
[ 741687-07-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3675 - 3678

4
4-azidocarbonyl-4-ethyl-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
[ 741687-07-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3675 - 3678

5
[ 188792-67-8 ]
[ 741687-07-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3675 - 3678

6
4-ethyl-4-isobutoxycarbonyloxycarbonyl-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
[ 741687-07-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3675 - 3678

7
[ 90536-66-6 ]
[ 741687-07-0 ]
tert-butyl 4-ethyl-4-([4-(methylsulfonyl)benzyl]amino}carbonyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 2: Preparation offers-butyl 4-ethyl-4-([4-(methylsulfonyl)benzyl]amino}carbonyl)piperidine-1 -carboxylate; .To a solution of [4-(methylsulfonyl)phenyl]acetic acid (395mg) in dichloromethane(20ml) was added disopropyldiethylamine (0.38ml) followed by HATU (VOOmg) and mixturewas stirred for 10 minutes before the addition of tert-butyl 4-amino-4-ethylpiperidine-l-carboxylate (420mg). The resulting mixture was stirred at room temperature for 18 hours. Thereaction mixture was partitioned between dichloromethane and water. The organic extractswere dried (MgSCU) and evaporated to dryness. The residue was purified chromatography onsilica eluting with gradient of ethyl acetate and isohexane to give the sub-title compound asan oil (750mg). NMR (CDC13): 0.9 (t, 3H), 1.5 (s, 9H), 1.5 (m, 2H), 1.9 (m, 2H), 2.1 (m, 2H),3.0 (m, 2H), 3.1 (s, 3H), 3.7 (s, 2H), 3.8 (m, 2H), 5.2 (s, 1H), 7.6 9d, 2H), 8.0 (d, 2H).

Reference： [1]Patent: WO2006/1752,2006,A1 .Location in patent: Page/Page column 81

8
[ 1258066-22-6 ]
[ 741687-07-0 ]
[ 1258066-31-7 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7: tert-hutyl 4-ethyl-4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin- 4( l/f,3/f,5H)-yl)piperidine- 1 -carboxylate[0168] 1 -tert-QvXy 4-methyl 3-formyl- lH-pyrrolo[2,3-delta]pyridine- 1 ,4-dicarboxylate (211 mg, 0.692 mmol) was dissolved in MeOH (10 mL) and tert-hvXy 4-amino-4- ethylpiperidine-1 -carboxylate (158 mg, 0.692 mmol) were added followed by 2 drops of acetic acid. The solution was allowed to stir at room temperature for 2 h. Then sodium cyanoborohydride (44 mg, 0.692 mmol) was added over the course of 6 h at room temperature. The solution was quenched with water and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated in vacuo. Purification by silica gel chromatography (70% EtOAc/Hexanes) gave 127 mg of l-tert-buty 4-methyl 3-((l -(tert- butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)- lH-pyrrolo[2,3-delta]pyridine- 1 ,A- dicarboxylate. [M+H] found 417.[0169] 1 -tert-BvXy 4-methyl 3 -(( 1 -(tert-butoxycarbonyl)-4-ethylpiperidin-4- ylamino)methyl)-lH-pyrrolo[2,3-delta]pyridine-l,4-dicarboxylate (123 mg, 0.238 mmol) was stirred in MeOH (3 mL), IN NaOH (3 mL), and THF (2 mL) for 16 h. The mixture was concentrated in vacuo. Purification via basic prep HPLC 20% to 50% B in A gave 60 mg of 3-((l-(fert-butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-lH-pyrrolo[2,3-6]pyridine-4-carboxylic acid. 1U NMR (400 MHz, CD3OD) delta 8.29 (d, IH, J= 4.8 Hz),7.68 (s, IH), 7.52 (d, IH, J= 5.1 Hz), 4.31 (s, 2H), 3.95-4.01 (m, IH), 2.03 (q, 2H, J= 7.6Hz), 1.92-1.94 (m, 4H), 1.47 (s, 9H), 1.46 (m, 2H), 1.07 (t, IH, J= 7.3 Hz). [M+H] found403.[0170] 3-((l-(tert-Butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-l/-f-pyrrolo[2,3-6]pyridine-4-carboxylic acid (50 mg, 0.124 mmol), HATU (94 mg, 0.248 mmol), and A- dimethylaminopyridine (46 mg, 0.373 mmol) were stirred in DMF (3 mL) at room temperature for 1 h. The solution was concentrated in vacuo to give the title compound which was used without further purification.

Reference： [1]Patent: WO2010/144486,2010,A1 .Location in patent: Page/Page column 34-35

9
[ 1207178-24-2 ]
[ 741687-07-0 ]

Reference： [1]Patent: WO2016/94824,2016,A1

10
C₁₃H₂₄N₂O₃ [ No CAS ]
[ 741687-07-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; potassium hydroxide; In acetonitrile; at 20℃;	To a solution of the compound 3 (20.5 g, 80 rnmoi) in CH3CN (200 ml) and 5N KOH (10() nil) was added i,3-dibromo-5,5-dimethylimidazohdine-2,4-diorie (11.1 g, 40nunol). The mixture was stirred overnight at room temperature. Afier completion, the mixture was concentrated to remove CH3CN. Adjustment of the pH of the water phase to 5 was with 2N HC1 in ice bath, the mixture was extracted with EA and separated i1en adjustment of the pH of water phase to 10. The precipitate was collected to afford the compound 4 (10 g, 55%) as a white solid.

Reference： [1]Patent: WO2016/94824,2016,A1 .Location in patent: Page/Page column 51; 52

11
[ 741687-07-0 ]
C₃₄H₄₄N₆O₄S [ No CAS ]

Reference： [1]Patent: WO2016/94824,2016,A1

12
[ 741687-07-0 ]
C₂₉H₃₆N₆O₂S [ No CAS ]

Reference： [1]Patent: WO2016/94824,2016,A1

13
[ 741687-07-0 ]
C₁₉H₂₈N₂O₄ [ No CAS ]

Reference： [1]Patent: WO2016/94824,2016,A1

14
[ 741687-07-0 ]
C₃₄H₄₄N₄O₅S [ No CAS ]

Reference： [1]Patent: WO2016/94824,2016,A1

15
[ 741687-07-0 ]
C₂₄H₂₈N₄OS*ClH [ No CAS ]

Reference： [1]Patent: WO2016/94824,2016,A1

16
[ 741687-07-0 ]
C₂₉H₃₅N₅O₃S [ No CAS ]

Reference： [1]Patent: WO2016/94824,2016,A1

17
[ 5798-75-4 ]
[ 741687-07-0 ]
C₂₁H₃₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos; In toluene; at 100℃;	A. solution of the compound 4 (1.0 g, 4.4 mmoi). ethyl 4-bromobenzoar.e (943 nig, 4.4 mmol), Pd2(dba)3 (202 mg, 0.22 mmol), Ruphos (103 mg, 0.22 nunol) arid Cs2CO3 (2.9 g, 8.8 inmol) in toluene (25 in) was stirred at 100C overnight. The mixture was concentrated and purified by silica gel column with EA:PE = 1:5 to affbrd compound 5 (1.0 g, 59%) as a light yellow solid.

Reference： [1]Patent: WO2016/94824,2016,A1 .Location in patent: Page/Page column 51; 52

18
[ 91419-52-2 ]
[ 741687-07-0 ]

Reference： [1]Patent: WO2016/94824,2016,A1

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H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
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Environmental hazards
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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

[ CAS No. 741687-07-0 ]

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[ 741687-07-0 ] Synthesis Path-Downstream 1~18

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Amines

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Piperidines

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[ 741687-07-0 ]

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[ 741687-07-0 ]