[ CAS No. 1016731-24-0 ] {[proInfo.proName]}

Name: 1016731-24-0|Benzyl 3-(aminomethyl)azetidine-1-carboxylate|98%
Brand: Ambeed
SKU: A679061
Rating: 94 (35 reviews)

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3d Animation Molecule Structure of 1016731-24-0

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Quality Control of [ 1016731-24-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1016731-24-0 ]

SDS Specification

Alternatived Products of [ 1016731-24-0 ]

Product Details of [ 1016731-24-0 ]

CAS No. :	1016731-24-0	MDL No. :	MFCD07772065
Formula :	C₁₂H₁₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BYCVYBQLKZYFBQ-UHFFFAOYSA-N
M.W :	220.27	Pubchem ID :	24692921
Synonyms :		Chemical Name :	Benzyl 3-(aminomethyl)azetidine-1-carboxylate

Calculated chemistry of [ 1016731-24-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	64.52
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) :	-7.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.43
Log Po/w (XLOGP3) :	0.71
Log Po/w (WLOGP) :	0.68
Log Po/w (MLOGP) :	1.14
Log Po/w (SILICOS-IT) :	1.0
Consensus Log Po/w :	1.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.6
Solubility :	5.53 mg/ml ; 0.0251 mol/l
Class :	Very soluble
Log S (Ali) :	-1.45
Solubility :	7.73 mg/ml ; 0.0351 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.48
Solubility :	0.729 mg/ml ; 0.00331 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 1016731-24-0 ]

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

Application In Synthesis of [ 1016731-24-0 ]

* 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 [ 1016731-24-0 ]

[ 1016731-24-0 ] Synthesis Path-Downstream 1~21

1
[ 2384368-92-5 ]
[ 1016731-24-0 ]
[ 2410576-62-2 ]

Yield	Reaction Conditions	Operation in experiment
0.09%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h;	92 Intermediate 92A: Benzyl 3-(((2-fluoro-4-(methoxycarbonyl)-6- nitrophenyl)amino)methyl)azetidine-1-carboxylate A mixture of methyl 4-chloro-3-fluoro-5-nitrobenzoate (600 mg, 2.57 mmol), benzyl 3-(aminomethyl)azetidine-1-carboxylate (566 mg, 2.57 mmol) and potassium carbonate (1065 mg, 7.71 mmol) in DMF (10 mL) was stirred at RT for 3 days. The mixture was diluted with EtOAc (15 mL) and was washed with a solution of aqueous saturated sodium bicarbonate (2 x 15 mL). The organic layer was dried over sodium sulfate and concentrated. The crude product was subjected to ISCO flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient) to yield benzyl 3-(((2-fluoro-4- (methoxycarbonyl)-6-nitrophenyl)amino)methyl)azetidine-1-carboxylate (1.02 mg, 2.322 mmol, 0.090 % yield) as light brown gum. LC/MS (M+H): 418; LC retention time: 1.00 min (analytical HPLC Method 3).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/33514, 2020, A1 Location in patent: Paragraph 00240

2
[ 63603-09-8 ]
[ 1016731-24-0 ]
[ 2410576-23-5 ]

Yield	Reaction Conditions	Operation in experiment
73.2%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h;	1 Intermediate 1A: Benzyl 3-(((2-methoxy-4-(methoxycarbonyl)-6- nitrophenyl)amino)methyl)azetidine-1-carboxylate A mixture of methyl 4-chloro-3-methoxy-5-nitrobenzoate (2.79 g, 11.35 mmol), benzyl 3-(aminomethyl)azetidine-1-carboxylate (2.5 g, 11.35 mmol) and potassium carbonate (4.71 g, 34.0 mmol) in DMF (20 mL) was stirred at 60 °C for 18 hours. The mixture was diluted with EtOAc (35 mL) and was washed with a solution of sodium sulfate and concentrated. The crude product was subjected to ISCO flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient) to yield benzyl 3-(((2- methoxy-4-(methoxycarbonyl)-6-nitrophenyl)amino)methyl)azetidine-1-carboxylate (3.755 g, 8.31 mmol, 73.2 % yield) as red gum. LC/MS (M+H): 430; LC retention time: 1.07 min (analytical HPLC Method 3). 1H NMR (499 MHz, CHLOROFORM-d) d 8.51 (d, J=1.9 Hz, 1H), 8.21 - 8.13 (m, 1H), 7.57 - 7.51 (m, 1H), 7.41 - 7.31 (m, 5H), 5.15 - 5.05 (m, 2H), 4.22 - 4.11 (m, 2H), 3.99 - 3.86 (m, 8H), 3.82 - 3.73 (m, 2H), 2.94 - 2.79 (m, 1H)

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/33514, 2020, A1 Location in patent: Paragraph 00188

3
[ 1016731-24-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 60 °C 2: sodium dithionite; water / ethanol / 4 h / 80 °C 3: water; sodium hydroxide / tetrahydrofuran / 18 h / 50 °C 4: triethylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C