[ CAS No. 916421-36-8 ] {[proInfo.proName]}

Name: 916421-36-8|tert-Butyl 3-(4-aminophenyl)azetidine-1-carboxylate|97%
Brand: Ambeed
SKU: A968821
Rating: 96 (29 reviews)

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2D 3D

Structure of 916421-36-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 916421-36-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 916421-36-8 ]

SDS Specification

Alternatived Products of [ 916421-36-8 ]

Product Details of [ 916421-36-8 ]

CAS No. :	916421-36-8	MDL No. :	MFCD08751348
Formula :	C₁₄H₂₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XCLKFXTWLPMSFY-UHFFFAOYSA-N
M.W :	248.32	Pubchem ID :	56956222
Synonyms :

Calculated chemistry of [ 916421-36-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	75.87
TPSA :	55.56 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.81
Log Po/w (XLOGP3) :	1.95
Log Po/w (WLOGP) :	2.23
Log Po/w (MLOGP) :	1.94
Log Po/w (SILICOS-IT) :	1.54
Consensus Log Po/w :	2.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.59
Solubility :	0.637 mg/ml ; 0.00257 mol/l
Class :	Soluble
Log S (Ali) :	-2.74
Solubility :	0.45 mg/ml ; 0.00181 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.88
Solubility :	0.328 mg/ml ; 0.00132 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 916421-36-8 ]

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 [ 916421-36-8 ]

* 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 [ 916421-36-8 ]
Downstream synthetic route of [ 916421-36-8 ]

[ 916421-36-8 ] Synthesis Path-Upstream 1~3

1
[ 883901-62-0 ]
[ 916421-36-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: With hydrogen In ethyl acetate for 18 h; Stage #2: With palladium 10% on activated carbon In ethyl acetate for 20 h;	(b) tert-Butyl 3-(4-aminophenyl) azetidine- 1-carboxylate (17)A suspension of 10percent Pd/C (0.320 g) and tert-butyl-3-(4-nitrophenyl)azetidine-1- carboxylate (16) (2.14 g, 7.68 mmol) in EtOAc (16 mL) was stirred under a hydrogen atmosphere for 18 hours. Additional 10percent Pd/C (1.00 g) was added and stirringcontinued for a further 20 hours. The resulting mixture was filtered through a pad ofCelite, washing with EtOAc, and the filtrate concentrated in vacuo to give the titlecompound I7as a light yellow/cream solid (1.80g, 94percent); 1H NMR (300 MHz, CDCI3)O 7.12 (d, J= 8.3 Hz, 2H), 6.69 (dd, J= 6.5, 1.9 Hz, 2H), 4.29 (t, J= 8.7 Hz, 2H),3.93 (dd, J= 8.4, 6.1 Hz, 2H), 3.65(brs, 2H), 1.55-1.68 (m, 1H), 1.48 (5, 9H). LCMS10 B: rt4.964 mm; m/z249 [M+H].

Reference： [1] Patent: WO2014/26243, 2014, A1, . Location in patent: Page/Page column 89
[2] Patent: WO2014/26242, 2014, A1, . Location in patent: Page/Page column 133; 134

2
[ 254454-54-1 ]
[ 916421-36-8 ]

Reference： [1] Patent: WO2014/26243, 2014, A1,
[2] Patent: WO2014/26242, 2014, A1,

3
[ 636-98-6 ]
[ 916421-36-8 ]

Reference： [1] Patent: WO2014/26243, 2014, A1,
[2] Patent: WO2014/26242, 2014, A1,

[ 916421-36-8 ] Synthesis Path-Downstream 1~21

1
[ 883901-62-0 ]
[ 916421-36-8 ]

Yield	Reaction Conditions	Operation in experiment
94%		(b) tert-Butyl 3-(4-aminophenyl) azetidine- 1-carboxylate (17)A suspension of 10% Pd/C (0.320 g) and tert-butyl-3-(4-nitrophenyl)azetidine-1- carboxylate (16) (2.14 g, 7.68 mmol) in EtOAc (16 mL) was stirred under a hydrogen atmosphere for 18 hours. Additional 10% Pd/C (1.00 g) was added and stirringcontinued for a further 20 hours. The resulting mixture was filtered through a pad ofCelite, washing with EtOAc, and the filtrate concentrated in vacuo to give the titlecompound I7as a light yellow/cream solid (1.80g, 94%); 1H NMR (300 MHz, CDCI3)O 7.12 (d, J= 8.3 Hz, 2H), 6.69 (dd, J= 6.5, 1.9 Hz, 2H), 4.29 (t, J= 8.7 Hz, 2H),3.93 (dd, J= 8.4, 6.1 Hz, 2H), 3.65(brs, 2H), 1.55-1.68 (m, 1H), 1.48 (5, 9H). LCMS10 B: rt4.964 mm; m/z249 [M+H].

Reference： [1]Patent: WO2014/26243,2014,A1 .Location in patent: Page/Page column 89
[2]Patent: WO2014/26242,2014,A1 .Location in patent: Page/Page column 133; 134

2
[ 916421-36-8 ]
[ 1566543-77-8 ]

Reference： [1]Patent: WO2014/26243,2014,A1

3
[ 916421-36-8 ]
[ 1566543-79-0 ]

Reference： [1]Patent: WO2014/26243,2014,A1

4
[ 916421-36-8 ]
[ 1566542-79-7 ]

Reference： [1]Patent: WO2014/26243,2014,A1

5
[ 916421-36-8 ]
[ 1566543-78-9 ]

Reference： [1]Patent: WO2014/26243,2014,A1

6
[ 916421-36-8 ]
[ 3932-97-6 ]
[ 1566543-57-4 ]

Yield	Reaction Conditions	Operation in experiment
56%		(C) tert-Butyl 3-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yI) amino) phenyl)azetidine1-carboxylate (K4)Zinc chloride (1.0 M in Et20) (4.83 mL, 4.83 mmol) was added to a solution of 2,4-dichloro-5-(trifluoromethyl)pyrimidine (0.769 g, 3.54 mmol) in 1:1 dichloroethane/teitbutanol (64 mL) at room temperature under nitrogen. After stirring for 10 minutes, teit-butyl 3-(4-am inophenyl)azetidine- 1 -carboxylate (17) (0.800 g, 3.22 m mol) was added followed by Et3N (1.08 mL, 7.73 mmol). The resulting mixture was stirred at room temperature for 20 hours then the volatiles removed in vacuo. Water wasadded to the solid residue and the resulting suspension sonicatated for 2 minutes.The suspension was filtered, and the filter cake dried then adsorbed onto silica geland purified using column chromatography (CombiFlash Rf, 40 g Si02 Cartridge, 10-40% EtOAc in cyclohexane) to give a white solid. The solid was suspended in MeOH(7 mL) and sonicated for 30 seconds. The resulting suspension was filtered and thefilter cake was washed with MeOH (3 mL) then dried to give the title compound K4 asa white solid (0.777 g, 56%); 1H NMR (300 MHz, d6-DMSO) 0 10.6 (5, 1H), 8.79 (5, 1H), 7.66 (d, J= 8.4 Hz, 2H), 7.33 (d, J= 8.4 Hz, 2H), 4.23 (t, J= 7.6 Hz, 2H), 3.80 (5, 3H), 1.40 (5, 9H). LCMS-B: rt 8.810 mm; m/z 429 [M+H].

Reference： [1]Patent: WO2014/26243,2014,A1 .Location in patent: Page/Page column 89
[2]Patent: WO2014/26242,2014,A1 .Location in patent: Page/Page column 133; 134

7
[ 254454-54-1 ]
[ 916421-36-8 ]

Reference： [1]Patent: WO2014/26243,2014,A1
[2]Patent: WO2014/26242,2014,A1

8
[ 636-98-6 ]
[ 916421-36-8 ]