[ CAS No. 77290-31-4 ] {[proInfo.proName]}

Name: 77290-31-4|tert-Butyl 4-(cyanomethyl)piperazine-1-carboxylate|96%
Brand: Ambeed
SKU: A697516
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3d Animation Molecule Structure of 77290-31-4

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Quality Control of [ 77290-31-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 77290-31-4 ]

SDS Specification

Alternatived Products of [ 77290-31-4 ]

Product Details of [ 77290-31-4 ]

CAS No. :	77290-31-4	MDL No. :	MFCD06795916
Formula :	C₁₁H₁₉N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OJUKCGDZZNLDPC-UHFFFAOYSA-N
M.W :	225.29	Pubchem ID :	21936030
Synonyms :

Calculated chemistry of [ 77290-31-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	67.96
TPSA :	56.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.57
Log Po/w (XLOGP3) :	0.71
Log Po/w (WLOGP) :	0.3
Log Po/w (MLOGP) :	0.22
Log Po/w (SILICOS-IT) :	0.35
Consensus Log Po/w :	0.83

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.42
Solubility :	8.56 mg/ml ; 0.038 mol/l
Class :	Very soluble
Log S (Ali) :	-1.48
Solubility :	7.53 mg/ml ; 0.0334 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.06
Solubility :	19.6 mg/ml ; 0.0871 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.44

Safety of [ 77290-31-4 ]

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 [ 77290-31-4 ]

* 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 [ 77290-31-4 ]

[ 77290-31-4 ] Synthesis Path-Downstream 1~45

1
[ 107-14-2 ]
[ 57260-71-6 ]
[ 77290-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃;	To a stirred solution of N-Boc piperazine (1 g) in dry THF (20 ml), triethylamine (3 ml), followed by chloroacetonitrile (5.02 ml) were added dropwise. The reaction mixture was allowed to stir at room temperature for overnight. The solvent was removed under vacuum and residue was diluted ethyl acetate (20 ml). The organic layer was concentrated to dryness under reduced pressure to afford tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate, which was used for the next reaction without further purification.1H NMR (400 MHz, CDCl3): delta 1.47 (s, 9H), 2.55 (t, 4H, J=6 Hz), 3.49 (t, 4H, J=4 Hz), 3.55 (s, 2H).GC MS: 225

Reference： [1]Monatshefte fur Chemie,2016,vol. 147,p. 2221 - 2234
[2]Patent: US2007/249579,2007,A1 .Location in patent: Page/Page column 132

2
[ 77290-31-4 ]
[ 294622-55-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyridine; hydrogen sulfide; triethylamine; In hexane; ethyl acetate;	tert-Butyl 4-thiocarbamoylmethylpiperazine-1-carboxylate A solution of tert-butyl 4-cyanomethylpiperazine-1-carboxylate (4.5 g, 0.020 mol) in a 3:1 mixture of triethylamine/pyridine (40 mL) at room temperature was bubbled with hydrogen sulfide for 30 minutes. The reaction mixture was stirred for 18 hours at room temperature and then concentrated under vacuum. The residue was treated with a mixture 1:4 mixture of ethyl acetate/hexane and the resulting solid was collected by filtration and washed with the ethyl acetate/hexane mixture to provide tert-butyl 4-thiocarbamoylmethyl-piperazine-1-carboxylate (3.93 g, 75%). H-NMR (dmso-d6): 9.87 (1H, bs), 9.07 (1H, bs), 3.35 (4H, t), 2.34 (4H, t), 1.29 (9H, s); LC/MS: M+1: 259.6.

Reference： [1]Patent: US2002/86996,2002,A1
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4296 - 4299

3
[ 57260-71-6 ]
[ 590-17-0 ]
[ 77290-31-4 ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12.0h;	INTERMEDIATE 18Terr-butyl 4-(lH-tetrazol-5-ylmethyi piperazine-l -cafboxylate (i-18)Step A: Tert-butyl 4-(cyanomethyl)piperazine-l-carboxylate; To a stirred solution of 2.7 g (15 mmol) of tert-butyl piperazine-l-carboxylate in 30 mL of anhydrous N^-dimethylformamide was added 2.4 g (17 mmol) of potassium carbonate followed by 2,1 g (17 mmol) of bromoacetonitrile. The resulting heterogeneous mixture was stirred at ambient temperature of 12 h, quenched with water then extracted with ethyl acetate. The combined organic layers were washed with water then brine, dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-75% acetone in hexanes gradient to afford the title compound as clear gum (1.0 g, 30%). 1H-NMR (500 MHz, CDC13) 5 3.53 (s, 2 H), 3.48 (t, J- 5.0 Hz, 4H), 2.53 (t, J - 5.0 Hz, 4H), 1.45 (s, 9H). LC-MS: m/z (ES) 226.2 (MH)

Reference： [1]Patent: WO2020/92196,2020,A1 .Location in patent: Page/Page column 93
[2]Patent: WO2012/12314,2012,A1 .Location in patent: Page/Page column 58
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4296 - 4299
[4]Organic Process Research and Development,2012,vol. 16,p. 741 - 747

4
[ 77290-31-4 ]
[ 909707-10-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4296 - 4299

5
[ 77290-31-4 ]
C₃₂H₃₉N₅O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4296 - 4299

6
[ 77290-31-4 ]
C₂₇H₃₁N₅OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4296 - 4299

7
[ 77290-31-4 ]
[ 349671-08-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4296 - 4299

8
[ 77290-31-4 ]
4-Methyl-2-[3'-(2-piperazin-1-yl-thiazol-4-yl)-biphenyl-3-yl]-pentanoic acid cyanomethyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4296 - 4299

9
ammonium chloride [ No CAS ]
[ 107-14-2 ]
[ 57260-71-6 ]
[ 77290-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	The 1-cyanomethylpiperazine used as a starting material was prepared as follows: A mixture of 1-(tert-butoxycarbonyl)piperazine (5 g), 2-chloroacetonitrile (1.9 ml), potassium carbonate (4 g) and DMF (20 ml) was stirred at anbient temperature for 16 hours. A saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using diethyl ether as eluent. There was thus obtained 1-(tert-butoxycarbonyl)-4-cyanomethylpiperazine as a solid (5.7 g); NMR Spectrum: (CDCl3) 1.45 (s, 9H), 2.5 (m, 4H), 3.45 (m, 4H), 3.55 (s, 2H).

Reference： [1]Patent: US2004/48881,2004,A1

10
[ 77290-31-4 ]
[ 1269430-46-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium azide; triethylamine hydrochloride; In toluene; at 80℃; for 12.0h;	Step B: Tert-butyl 4-(lH etrazoi-5-ylmethyl)piperazine-l-carboxylate (i-18); To a stirred suspension of 1.50 g (6.66 mmol) of the title compound from Step A above in 25 mL of anhydrous toluene was added 1.38 g (10.0 mol) of triethylaminehydrochloride followed by 0.65 g (10 mmol) of sodium azide. The resuling mixture was heated to 80 C for 12 h then cooled to ambient temperature. All volatiles were removed in vacuo, and the residue suspended in 5 mL of brine and 1.0 N aqueous hydrogen chloride solution was added until pH of ~4 was achieved. The aqueous phase was extracted with chloroform and the combined organics were dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-100% acetone in hexanes gradient to afford the title compound (i-18) as white solid (1.1 g, 63%). 1H-NM (500 MHz, DMSO<¼) delta 3.82 (s, 2 H), 3.29 (br s, 4H), 2.38-2.34 (m, 4H), 1.36 (s, 9H). LC-MS: mJz (ES) 269.0 (MH)+.

Reference： [1]Patent: WO2012/12314,2012,A1 .Location in patent: Page/Page column 58-59

11
[ 77290-31-4 ]
1-(1H-tetrazol-5-ylmethyl)piperazine bistrifluoroacetic acid salt [ No CAS ]

Reference： [1]Patent: WO2012/12314,2012,A1

12
[ 77290-31-4 ]
[ 1040631-47-7 ]

Reference： [1]Patent: WO2020/92196,2020,A1 .Location in patent: Page/Page column 93-94
[2]Organic Process Research and Development,2012,vol. 16,p. 741 - 747

13
[ 77290-31-4 ]
[ 927210-23-9 ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 741 - 747
[2]Organic Process Research and Development,2012,vol. 16,p. 741 - 747

14
[ 77290-31-4 ]
[ 1314217-69-0 ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 741 - 747
[2]Organic Process Research and Development,2012,vol. 16,p. 741 - 747

15
[ 77290-31-4 ]
C₂₉H₃₄F₃N₅O₆ [ No CAS ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 741 - 747

16
[ 24424-99-5 ]
[ 77290-31-4 ]