[ CAS No. 550378-39-7 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 550378-39-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 550378-39-7 ]

SDS Specification

Alternatived Products of [ 550378-39-7 ]

Product Details of [ 550378-39-7 ]

CAS No. :	550378-39-7	MDL No. :	MFCD06796559
Formula :	C₁₂H₁₇ClN₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	QNQVBYGRFHOBNO-MERQFXBCSA-N
M.W :	256.73	Pubchem ID :	20820180
Synonyms :

Calculated chemistry of [ 550378-39-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	71.49
TPSA :	55.56 ?2

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) :	0.0
Log Po/w (XLOGP3) :	1.68
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	0.89
Consensus Log Po/w :	1.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.49
Solubility :	0.836 mg/ml ; 0.00326 mol/l
Class :	Soluble
Log S (Ali) :	-2.46
Solubility :	0.888 mg/ml ; 0.00346 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.35
Solubility :	1.13 mg/ml ; 0.00442 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.67

Safety of [ 550378-39-7 ]

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 [ 550378-39-7 ]

* 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 [ 550378-39-7 ]
Downstream synthetic route of [ 550378-39-7 ]

[ 550378-39-7 ] Synthesis Path-Upstream 1~2

1
[ 122536-74-7 ]
[ 550378-39-7 ]

Reference： [1] Patent: US2004/10017, 2004, A1, . Location in patent: Page/Page column 13; 17
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1690 - 1694

2
[ 501-53-1 ]
[ 550378-39-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1690 - 1694

[ 550378-39-7 ] Synthesis Path-Downstream 1~8

1
[ 208772-42-3 ]
[ 550378-39-7 ]
[ 400653-25-0 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 24.0h;	1-Cbz-3S-[[1-(t-butyloxycarboxy)indol-6-yl]carbonyl]-aminopyrrolidine [CHEMMOL-00020] [0247] To a solution of the compound from Part B (6.95 g, 21.7 mmol) in glacial HOAc (40 mL) was added anisole (4 mL), and HCl gas was bubbled into reaction for 20 min. The reaction solvent was removed in vacuo and the residue was triturated with Et2O (200 mL). The solid was filtered and dried to give 5.7 g of <strong>[550378-39-7]1-Cbz-3S-aminopyrrolidine hydrochloride</strong> salt. [0248] To a solution of the hydrochloride salt (0.49 g, 1.91 mmol) in DMF (20 mL) was added 1-t-butyloxycarbonylindole-6-carboxylic acid (0.5 g, 1.91 mmol), diisopropylethylamine (0.33 mL, 1.91 mmol), HOBt (0.26 g, 1.91 mmol), and DCC (0.4 g, 1.91 mmol). The reaction was stirred for 24 h at room temperature. The resultant precipitate was removed by filtration, and the mother liquor was concentrated in vacuo to an oil. The resultant oil was dissolved in EtOAc (250 mL) and washed sequentially with 1 N NaHCO3, water, 1.5 N citric acid, and water. The organic layer was dried (MgSO4) and evaporated in vacuo to an amorphous solid of the crude title compound (0.87 g, 98%). [0249] TLC Rf (D) 0.64; [0250] MS 464 (M+H)+.; 1-Cbz-3S-[[1-(t-Butyloxycarbonyl)indol-6-yl]carbonyl]-aminopyrrolidine [0331] The title compound was prepared according to the procedure described in Example 2C.

Reference： [1]Patent: US2004/10017,2004,A1 .Location in patent: Page/Page column 13; 17

2
[ 122536-74-7 ]
[ 550378-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid; In methoxybenzene; for 0.333333h;	1-Cbz-3S-[[1-(t-butyloxycarboxy)indol-6-yl]carbonyl]-aminopyrrolidine [CHEMMOL-00020] [0247] To a solution of the compound from Part B (6.95 g, 21.7 mmol) in glacial HOAc (40 mL) was added anisole (4 mL), and HCl gas was bubbled into reaction for 20 min. The reaction solvent was removed in vacuo and the residue was triturated with Et2O (200 mL). The solid was filtered and dried to give 5.7 g of 1-Cbz-3S-aminopyrrolidine hydrochloride salt. [0248] To a solution of the hydrochloride salt (0.49 g, 1.91 mmol) in DMF (20 mL) was added 1-t-butyloxycarbonylindole-6-carboxylic acid (0.5 g, 1.91 mmol), diisopropylethylamine (0.33 mL, 1.91 mmol), HOBt (0.26 g, 1.91 mmol), and DCC (0.4 g, 1.91 mmol). The reaction was stirred for 24 h at room temperature. The resultant precipitate was removed by filtration, and the mother liquor was concentrated in vacuo to an oil. The resultant oil was dissolved in EtOAc (250 mL) and washed sequentially with 1 N NaHCO3, water, 1.5 N citric acid, and water. The organic layer was dried (MgSO4) and evaporated in vacuo to an amorphous solid of the crude title compound (0.87 g, 98%). [0249] TLC Rf (D) 0.64; [0250] MS 464 (M+H)+.; 1-Cbz-3S-[[1-(t-Butyloxycarbonyl)indol-6-yl]carbonyl]-aminopyrrolidine [0331] The title compound was prepared according to the procedure described in Example 2C.
	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 1.0h;	General procedure: A 200 mL round bottom flask was charged with (S)-tert-butyl 1-phenethylpiperidin-3-ylcarbamate (Intermediate 1; 388 mg, 1.27 mmol). 4 N HCl/dioxane (5.0 mL) was added, and the resulting solution was allowed to stir at room temperature. After 1 hour, the reaction was concentrated under reduced pressure. The residue was dissolved in MeOH and the solution was reconcentrated. The resulting material was used directly without further purification.

Reference： [1]Patent: US2004/10017,2004,A1 .Location in patent: Page/Page column 13; 17
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1690 - 1694

3
[ 550378-39-7 ]
[ 1253856-46-0 ]
[ 1253856-48-2 ]