[ CAS No. 17193-28-1 ] {[proInfo.proName]}

Name: 17193-28-1|1-Amino-1-cyclopentanecarboxamide|97%
Brand: Ambeed
SKU: A169998
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2D 3D

Structure of 17193-28-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 17193-28-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17193-28-1 ]

SDS Specification

Alternatived Products of [ 17193-28-1 ]

Product Details of [ 17193-28-1 ]

CAS No. :	17193-28-1	MDL No. :	MFCD01735313
Formula :	C₆H₁₂N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YGVGITVCEHRBDK-UHFFFAOYSA-N
M.W :	128.17	Pubchem ID :	11116086
Synonyms :

Calculated chemistry of [ 17193-28-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.49
TPSA :	69.11 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) :	-7.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.17
Log Po/w (XLOGP3) :	-0.95
Log Po/w (WLOGP) :	-0.26
Log Po/w (MLOGP) :	-0.41
Log Po/w (SILICOS-IT) :	0.07
Consensus Log Po/w :	-0.07

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.03
Solubility :	137.0 mg/ml ; 1.07 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.02
Solubility :	123.0 mg/ml ; 0.962 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.45
Solubility :	45.7 mg/ml ; 0.356 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.19

Safety of [ 17193-28-1 ]

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 [ 17193-28-1 ]

* 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 [ 17193-28-1 ]
Downstream synthetic route of [ 17193-28-1 ]

[ 17193-28-1 ] Synthesis Path-Upstream 1~9

1
[ 49830-37-7 ]
[ 17193-28-1 ]

Yield	Reaction Conditions	Operation in experiment
27%	Stage #1: With sulfuric acid In dichloromethane at 15 - 40℃; for 1 h; Stage #2: With ammonia In dichloromethane; water at 0℃;	Preparation of 3-(1-Carbamoyl-1-cyclopentylamino)-1-propanesulfonic acid (Compound OT); To a 250 mL 1 neck flask containing 30percent NH₄OH (120 mL) was added NaCN (15.34 g, 0.31 mol) and NH₄Cl (19.75 g, 0.37 mol) with vigorous stirring. The corresponding ketone was added dropwise within 20 minutes at room temperature. The mixture was stirred for 3 days at room temperature follwed by extraction with dichloromehtnae (50 mL). The organic layer was separated and dried over anhydrous sodium sulfate for 2 hours. The sodium sulfate was removed by filtration, the solvent was removed under reduced pressure to yield the crude aminonitrile. The desired material was obtained as colorless oil after distillation under reduced pressure (14.03 g, 127 mmol, 51percent yield). Used as such. ¹H NMR (500 MHz, DMSO-d₆) δ 1.61-1.71 (m, 2H), 1.72-1.83(m, 4H), 1.8-1.94 (m, 2H), 2.42 (s, 2H); ¹³C NMR (125 MHz, DMSO-d₆) 23.0, 40.0, 54.2, 125.7 To 10 g of concentrated sulfuric acid stirred in an ice cooled water bath was added dropwise a solution of the aminonitrille (41 mmol). in 30 mL CH₂Cl₂, maintaining the internal temperature at 15° C. Then the bath was removed and the mixture heated to 40° C. for 1 hour. The mixture was cooled in ac ice bath and poured onto 200 g of crushed ice. The mixture was made pH 7-8 with 28percent aqueous NH₃and extracted with EtOAc (3.x.100 mL). The extracts were collected, dried (MgSO₄), and evaporated to dryness. The crude solid was recrystallized in EtOAc/Hex. The desired material was obtained as a white solid 1.36 g, 10.6 mmol, 27percent. ¹H NMR (500 MHz, DMSO-d₆) δ 1.37-1.41 (m, 2H), 1.57-1.63 (m, 2H), 1.68-1.76 (m, 2H), 1.78 (br s, 2H), 1.88-1.94 (m, 2H), 6.91 (br s, 1H), 7.40 (br s, 1H); ¹³C NMR (125 MHz, DMSO-d₆) 24.2, 39.3, 64.7, 180.0. A solution of 1,3-propane sultone (1M, 6.30 mL) in toluene was added to a solution of 2-amino-2-methylpropaneamide (0.4350 g, 4.26 mmol) in MTBK (7 mL) and ethanol (0.5 mL). The mixture was heated to reflux for 4 hours then cooled to room temperature. The solid was collected by suction filtration, rinsed with acetone (2.x.5 mL). The solid was dried 18 hours at 60° C. in the vacuum oven (0.74 g). The solid was recrystallized in ethanol (5 mL) and water (5 mL). After drying, the title compound was obtained as a fine white solid (0.39 g, 2.80 mmol, 45percent). ¹H NMR (500 MHz, D₂O) δ 1.72-1.76 (m, 4H), 1.91-2.02 (m, 4H), 2.08-2.14- (m, 2H), 2.86 (t, J=7.3 Hz, 2H), 3.00 (t, J=7.6 Hz, 2H); ¹³C NMR (125 MHz, D₂O) 22.0, 24.6, 34.8, 43.3, 48.0, 72.4, 174.8; ES-MS 249 (M-H)

Reference： [1] Patent: US2006/223855, 2006, A1, . Location in patent: Page/Page column 157

2
[ 711603-83-7 ]
[ 17193-28-1 ]

Reference： [1] Tetrahedron Letters, 2008, vol. 49, # 17, p. 2743 - 2747
[2] Patent: US6800761, 2004, B1, . Location in patent: Page column 7

3
[ 17191-51-4 ]
[ 17193-28-1 ]

Reference： [1] Journal of the Chemical Society. Perkin transactions 1, 1968, vol. 5, p. 531 - 540

4
[ 17191-44-5 ]
[ 17193-28-1 ]

Reference： [1] Journal of the Chemical Society. Perkin transactions 1, 1968, vol. 5, p. 531 - 540

5
[ 52-52-8 ]
[ 17193-28-1 ]

Reference： [1] Journal of the Chemical Society. Perkin transactions 1, 1968, vol. 5, p. 531 - 540

6
[ 16248-83-2 ]
[ 17193-28-1 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1967, vol. 37, p. 805 - 808[2] Zhurnal Obshchei Khimii, 1967, vol. 37, p. 856 - 859

7
[ 22649-37-2 ]
[ 17193-28-1 ]

Reference： [1] Journal of the Chemical Society, 1960, p. 2119 - 2132

8
[ 17193-28-1 ]
[ 638-29-9 ]
[ 138402-05-8 ]

Reference： [1] Tetrahedron Letters, 2008, vol. 49, # 17, p. 2743 - 2747

9
[ 17193-28-1 ]
[ 138402-05-8 ]

Reference： [1] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 115 - 127

[ 17193-28-1 ] Synthesis Path-Downstream 1~88

1
[ 5241-63-4 ]
[ 17193-28-1 ]
[ 17193-46-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540

2
[ 17193-28-1 ]
[ 25084-39-3 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1969,vol. 5,p. 2058 - 2062
Zhurnal Organicheskoi Khimii,1969,vol. 5,p. 2119 - 2124

3
[ 16248-83-2 ]
[ 17193-28-1 ]

Reference： [1]Journal of general chemistry of the USSR,1967,vol. 37,p. 805 - 808
Zhurnal Obshchei Khimii,1967,vol. 37,p. 856 - 859

4
[ 17191-51-4 ]
[ 17193-28-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540

5
[ 22649-37-2 ]
[ 17193-28-1 ]

Reference： [1]Journal of the Chemical Society,1960,p. 2119 - 2132

6
[ 17193-28-1 ]
[ 25074-20-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1969,vol. 5,p. 2058 - 2062
Zhurnal Organicheskoi Khimii,1969,vol. 5,p. 2119 - 2124

7
[ 17193-28-1 ]
(S)-Pyrrolidine-2-carboxylic acid [(S)-1-(1-carbamoyl-cyclopentylcarbamoyl)-3-methyl-butyl]-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1441 - 1447

8
1-aminocyclopentanecarbonitrile hydrochloride [ No CAS ]
[ 17193-28-1 ]

Reference： [1]Journal of general chemistry of the USSR,1967,vol. 37,p. 805 - 808
Zhurnal Obshchei Khimii,1967,vol. 37,p. 856 - 859

9
[ 17193-28-1 ]
[ 17193-66-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540

10
[ 17191-44-5 ]
[ 17193-28-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540

11
[ 52-52-8 ]
[ 17193-28-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540

12
[ 17193-28-1 ]
[ 638-29-9 ]
[ 253269-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran;	3 g of the compound prepared in the preceding step are placed in 70 ml of anhydrous THF and 3.3 ml of triethylamine, and 3 ml of valeryl chloride in 10 ml of anhydrous THF are added with stirring. A white suspension forms. The intermediate compound formed, but not isolated, is (N-valeryl)-<strong>[17193-28-1]1-aminocyclopentanecarboxamide</strong>. 6 g of potassium hydroxide pellets, 7 ml of water and 16 ml of methanol are added. The mixture is refluxed for 2 and a half hours, followed by addition of 9 g of ammonium chloride. After stirring this mixture for 15 minutes, it is concentrated under vacuum. The residue obtained is taken up in 40 ml of water and extracted with 10 ml of ethyl acetate and then with twice 5 ml of ethyl acetate. The combined organic phases are dried over sodium sulfate and filtered. The filtrate is concentrated to dryness. 4.85 g of the expected product are obtained. The NMR spectrum is similar to that described above. The hydrochloride of this compound can be prepared by adding concentrated hydrochloric acid. The hydrochloride melts at 240 C. with sublimation.

Reference： [1]Patent: US6800761,2004,B1 .Location in patent: Page column 7

13
[ 711603-83-7 ]
[ 17193-28-1 ]

Yield	Reaction Conditions	Operation in experiment
		5.1 g of the oxalate obtained in the preceding step are treated with 7.65 ml of concentrated sulfuric acid (d=1.84) for 45 minutes with stirring. An evolution of gas is observed and the temperature increases to 100 C. The mixture is cooled to about 35 C. and is poured into an ice/concentrated aqueous ammonia mixture (10 g/2.8 ml). The suspension formed is extracted 6 times in succession with chloroform containing 5% methanol. 3 ml of aqueous ammonia (d=0.92) is added to the aqueous phase and extraction is repeated with chloroform containing methanol (1/0.5; v/v). The combined organic phases are dried over sodium sulfate, filtered and concentrated. The expected product is obtained in the form of a white solid. [00087] m=3.79 g [00088] m.p.=95 C. [00089] The results of the analysis and the IR spectrum confirm the structure.

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 2743 - 2747
[2]Patent: US6800761,2004,B1 .Location in patent: Page column 7

14
[ 17193-28-1 ]
[ 638-29-9 ]
[ 177219-40-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In dichloromethane; water; at 0 - 20℃;	11.5 g (90 mmol) of <strong>[17193-28-1]1-aminocyclopentanecarboxamide</strong> were suspended in 16 ml of methylene chloride. Then, 270 ml of a 25% solution of K2CO3 were added and the mixture was cooled to 0-5C. At this temperature, 13 ml (108 mmol) of valeroyl chloride were slowly added while vigorously stirring. The reaction mixture was stirred for 2h at 0-5C and 1h at room temperature Then, the product was filtered and washed with water and methanol. The wet product was dried. Yield: 18g (99%).
87.3%	With triethylamine; In tetrahydrofuran; at 10 - 30℃; for 1h;	Example 5: Mw grams, volume mmol Eq. 1-Aminocyclopentane 128. 2 12.8 g 100 1. 0 carboxylic acid amide Valeroyl Chloride 120. 6 13.3 g, 13.0 mL 110 1. 1 Triethyl amine 101. 2 13.2 g, 18.1 mL 130 1. 3 THF Total 100 mL 21. 2 g <strong>[17193-28-1]1-AMINOCYCLOPENTANE carboxylic acid amide</strong> was suspended in a mixture of dry THF (80 mL) and Et3N and cooled to 10 C. A Solution of valeroyl chloride in THF (20 mL) was slowly added with vigorous (preferably mechanical) stirring. The reaction temperature was kept below 30 C and the resulted suspension was vigorously stirred for 1 h at room temperature (TLC monitoring: CH2CL2/MEOH 8: 1). The solvent was evaporated under reduced pressure and the white residue was suspended in water (200 mL) and stirred for 20 min at room temperature. The solid was filtered, washed two times with water (total 100 mL) and methyl t-butyl ether (30 mL) and dried at 50 C/10 MMHG until constant weight to give 18.5 g (87.3 % yield) OF M-23 as a white powder pure by NMR. This product was used without additional purification.
	With triethylamine; In dichloromethane; at 0℃;	General procedure: <strong>[17193-28-1]1-amino-cyclopentanecarboxamide</strong> (3) (8.0 g, 62.5 mmol) was acylated with alkyl acyl chloride (93.7 mmol) and triethylamine (17.3 mL, 125.0 mmol) in 50 mL dichloromethane(DCM) at 0 C.After the reaction was completed, the resulting mixture was addedwith 30 mLwater, and extracted with DCM (25 mL 3). The organiclayer was dried over MgSO4. After filtration, the solvent wasremoved under reduced pressure. The residue was dissolved in50 mL MeOH and then 50 mL 10 M KOH was added slowly. Themixturewas refluxed for 3 h. After cooled to room temperature, themixture was added 50 mL H2O and extracted with DCM(30 mL 4). The organic layer was dried over MgSO4, the solventwas removed under reduced pressure. The resulting residue waspurified by CC to give 5a-d.

Reference： [1]Patent: EP2194050,2010,A1 .Location in patent: Page/Page column 10; 11
[2]Patent: WO2004/72064,2004,A1 .Location in patent: Page 18
[3]European Journal of Medicinal Chemistry,2016,vol. 123,p. 115 - 127

15
2-butyl-1,3-diaza-spiro [4.4]nonan4-one [ No CAS ]
[ 110-62-3 ]
[ 17193-28-1 ]
[ 151257-03-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With ammonia; In hexane; water;	EXAMPLE 3 Preparation of 2-butyl-1,3-diaza-spiro[4.4]nonan-4-one (DSPC) Ammonia solution (20%; 20 g, 0.30 mol.) is added to a solution of 126 g of <strong>[17193-28-1]1-aminocyclopentanecarboxamide</strong> (>98%, 0.98 mol.) in 150 g of water. 86 g of valeraldehyde (0.99 mol.) are then added at 15 C., during which the temperature rises to 32 C. The reaction mixture is heated to 70 C. and stirred for 7 hours at that temperature. 350 ml of MIBK are added to the emulsion, and the mixture is cooled, with stirring, and the organic phase is separated off. The extract is extensively concentrated by evaporation (200 g), and 200 g of n-hexane are added, and the crystals are filtered off. After drying there remain 125 g of 2-butyl-1,3-diaza-spiro [4.4]nonan4-one (HPLC: 98.6%). The hexane phase is concentrated to about 2/3 and cooled to 15 C. A further 22 g of product are isolated, corresponding to a yield of 73% of the theoretical yield. 1 H-NMR (500 MHz, DMSO-d6): delta=0.90 ppm (t, 3-H), 1.20-1.70 (m, 14-H), 1.80-1.95 (m, 1-H), 4.30 (t, 1-H), 8.20 (s, 1-H). 13 C-NMR (125 MHz, DMSO-d6): delta=18.8 ppm, 22.0, 24.7, 26.4, 36.0, 36.2, 36.9, 67.5, 68.1, 179.9.

Reference： [1]Patent: US6037474,2000,A

16
[ 13820-09-2 ]
[ 17193-28-1 ]
2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.4%	In acetone;	EXAMPLE 1 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-one-monohydrochloride 20 g (0.156 mol) of <strong>[17193-28-1]1-aminocyclopentane-1-carboxamide</strong> and 31 g (0.19 mol) of trimethyl orthovalerate are refluxed at 70-80 C. inner temperature for 1 hour. The condenser is then changed to a "No hold up" condenser, while heating and stirring are continued to distille off volatile components. The reaction is completed in vacuo. The residue is dissolved in 150 ml of acetone the pH is adjusted to 1-2, after cooling the resulting suspension the product is filtered off. 31 g of the title compound is obtained, yield 86.4%. IR: 3600-2200: vibr, NH; 1779: gammac=o; 1642 gammac, 1517: deltaNH (IRFT Perkin Elmer)

Reference： [1]Patent: US6162923,2000,A

17
[ 17193-28-1 ]
1,3-diaza-spiro [4.4] non-1-en-4-one monohydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.2%	With trimethyl orthoformate; In acetone;	EXAMPLE 2 1,3-diazaspiro[4,4]non-1-en-4-one monohydrochloride 20 g (0.156 mol) of <strong>[17193-28-1]1-aminocyclopentane-1-carboxamide</strong> and 28 g (0.19 mol) of trimethyl orthoformate are refluxed for 1 hour. The condenser is then changed to a "No hold up" condenser, and the temperature is elevated to 140 C. inner temperature. The residue is dissolved in 150 ml of acetone the pH is adjusted to 1-2 with concentrated hydrochloric acid and after cooling the resulting suspension the product is filtered of. 25 g of the title compound is obtained, yield 92.2%. Mp: 219-221 C. (decomp.) IR: 1663 cm-1 C=N 1739 cm-1 C=O 3197 cm-1 H(NH)

Reference： [1]Patent: US6162923,2000,A

18
[ 19810-31-2 ]
[ 17193-28-1 ]
[ 584-08-7 ]
[ 168274-59-7 ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	1-(2-Benzyloxyacetamido)-cyclopentyl-1-carboxamide, 13a Benzyloxyacetylchloride (16.7 g) was added to a mixture of <strong>[17193-28-1]1-aminocyclopentan-1-carboxamide</strong> (10.2 g), K2 CO3 (13.3 g) and acetone (150 ml) at -5 to 0 C. After stirring at room temperature for 2 h the reaction mixture was filtered. The precipitate was extracted with diethyl ether (50 ml) washed with water (100 ml) and dried at 50 C. in vacuo for 18 h giving the title compound as a crystalline material: 13.8 g.

Reference： [1]Patent: US5703087,1997,A

19
[ 49830-37-7 ]
[ 17193-28-1 ]

Yield	Reaction Conditions	Operation in experiment
27%		Preparation of 3-(1-Carbamoyl-1-cyclopentylamino)-1-propanesulfonic acid (Compound OT); To a 250 mL 1 neck flask containing 30% NH4OH (120 mL) was added NaCN (15.34 g, 0.31 mol) and NH4Cl (19.75 g, 0.37 mol) with vigorous stirring. The corresponding ketone was added dropwise within 20 minutes at room temperature. The mixture was stirred for 3 days at room temperature follwed by extraction with dichloromehtnae (50 mL). The organic layer was separated and dried over anhydrous sodium sulfate for 2 hours. The sodium sulfate was removed by filtration, the solvent was removed under reduced pressure to yield the crude aminonitrile. The desired material was obtained as colorless oil after distillation under reduced pressure (14.03 g, 127 mmol, 51% yield). Used as such. 1H NMR (500 MHz, DMSO-d6) delta 1.61-1.71 (m, 2H), 1.72-1.83(m, 4H), 1.8-1.94 (m, 2H), 2.42 (s, 2H); 13C NMR (125 MHz, DMSO-d6) 23.0, 40.0, 54.2, 125.7 To 10 g of concentrated sulfuric acid stirred in an ice cooled water bath was added dropwise a solution of the aminonitrille (41 mmol). in 30 mL CH2Cl2, maintaining the internal temperature at 15 C. Then the bath was removed and the mixture heated to 40 C. for 1 hour. The mixture was cooled in ac ice bath and poured onto 200 g of crushed ice. The mixture was made pH 7-8 with 28% aqueous NH3 and extracted with EtOAc (3×100 mL). The extracts were collected, dried (MgSO4), and evaporated to dryness. The crude solid was recrystallized in EtOAc/Hex. The desired material was obtained as a white solid 1.36 g, 10.6 mmol, 27%. 1H NMR (500 MHz, DMSO-d6) delta 1.37-1.41 (m, 2H), 1.57-1.63 (m, 2H), 1.68-1.76 (m, 2H), 1.78 (br s, 2H), 1.88-1.94 (m, 2H), 6.91 (br s, 1H), 7.40 (br s, 1H); 13C NMR (125 MHz, DMSO-d6) 24.2, 39.3, 64.7, 180.0. A solution of 1,3-propane sultone (1M, 6.30 mL) in toluene was added to a solution of 2-amino-2-methylpropaneamide (0.4350 g, 4.26 mmol) in MTBK (7 mL) and ethanol (0.5 mL). The mixture was heated to reflux for 4 hours then cooled to room temperature. The solid was collected by suction filtration, rinsed with acetone (2×5 mL). The solid was dried 18 hours at 60 C. in the vacuum oven (0.74 g). The solid was recrystallized in ethanol (5 mL) and water (5 mL). After drying, the title compound was obtained as a fine white solid (0.39 g, 2.80 mmol, 45%). 1H NMR (500 MHz, D2O) delta 1.72-1.76 (m, 4H), 1.91-2.02 (m, 4H), 2.08-2.14- (m, 2H), 2.86 (t, J=7.3 Hz, 2H), 3.00 (t, J=7.6 Hz, 2H); 13C NMR (125 MHz, D2O) 22.0, 24.6, 34.8, 43.3, 48.0, 72.4, 174.8; ES-MS 249 (M-H)

Reference： [1]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 157

20
[ 1120-71-4 ]
[ 17193-28-1 ]
3-(1-carbamoyl-1-cyclopentylamino)-1-propanesulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	In 3,3-dimethyl-butan-2-one; toluene; for 4h;Heating / reflux;	Preparation of 3-(1-Carbamoyl-1-cyclopentylamino)-1-propanesulfonic acid (Compound OT); To a 250 mL 1 neck flask containing 30% NH4OH (120 mL) was added NaCN (15.34 g, 0.31 mol) and NH4Cl (19.75 g, 0.37 mol) with vigorous stirring. The corresponding ketone was added dropwise within 20 minutes at room temperature. The mixture was stirred for 3 days at room temperature follwed by extraction with dichloromehtnae (50 mL). The organic layer was separated and dried over anhydrous sodium sulfate for 2 hours. The sodium sulfate was removed by filtration, the solvent was removed under reduced pressure to yield the crude aminonitrile. The desired material was obtained as colorless oil after distillation under reduced pressure (14.03 g, 127 mmol, 51% yield). Used as such. 1H NMR (500 MHz, DMSO-d6) delta 1.61-1.71 (m, 2H), 1.72-1.83(m, 4H), 1.8-1.94 (m, 2H), 2.42 (s, 2H); 13C NMR (125 MHz, DMSO-d6) 23.0, 40.0, 54.2, 125.7 To 10 g of concentrated sulfuric acid stirred in an ice cooled water bath was added dropwise a solution of the aminonitrille (41 mmol). in 30 mL CH2Cl2, maintaining the internal temperature at 15 C. Then the bath was removed and the mixture heated to 40 C. for 1 hour. The mixture was cooled in ac ice bath and poured onto 200 g of crushed ice. The mixture was made pH 7-8 with 28% aqueous NH3 and extracted with EtOAc (3×100 mL). The extracts were collected, dried (MgSO4), and evaporated to dryness. The crude solid was recrystallized in EtOAc/Hex. The desired material was obtained as a white solid 1.36 g, 10.6 mmol, 27%. 1H NMR (500 MHz, DMSO-d6) delta 1.37-1.41 (m, 2H), 1.57-1.63 (m, 2H), 1.68-1.76 (m, 2H), 1.78 (br s, 2H), 1.88-1.94 (m, 2H), 6.91 (br s, 1H), 7.40 (br s, 1H); 13C NMR (125 MHz, DMSO-d6) 24.2, 39.3, 64.7, 180.0. A solution of 1,3-propane sultone (1M, 6.30 mL) in toluene was added to a solution of 2-amino-2-methylpropaneamide (0.4350 g, 4.26 mmol) in MTBK (7 mL) and ethanol (0.5 mL). The mixture was heated to reflux for 4 hours then cooled to room temperature. The solid was collected by suction filtration, rinsed with acetone (2×5 mL). The solid was dried 18 hours at 60 C. in the vacuum oven (0.74 g). The solid was recrystallized in ethanol (5 mL) and water (5 mL). After drying, the title compound was obtained as a fine white solid (0.39 g, 2.80 mmol, 45%). 1H NMR (500 MHz, D2O) delta 1.72-1.76 (m, 4H), 1.91-2.02 (m, 4H), 2.08-2.14- (m, 2H), 2.86 (t, J=7.3 Hz, 2H), 3.00 (t, J=7.6 Hz, 2H); 13C NMR (125 MHz, D2O) 22.0, 24.6, 34.8, 43.3, 48.0, 72.4, 174.8; ES-MS 249 (M-H)

Reference： [1]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 157

21
[ 17193-28-1 ]
[ 638-29-9 ]
[ 138402-05-8 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 2743 - 2747

22
[ 168273-07-2 ]
[ 17193-28-1 ]
C₂₄H₂₃Cl₃N₄O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4496 - 4510

23
[ 5271-67-0 ]
[ 17193-28-1 ]
[ 1199814-93-1 ]

Yield	Reaction Conditions	Operation in experiment
93%		I-Aminocyclopentanecarboxamide (12.8 g, 0.1 mol) was dissolved in anhydrous THF (300 ml) and TEA (15.2 ml, 11 g, 0.11 mol) was added. 2-Thenoylchloride (16.1 g, 0.11 mol) in anhydrous THF (30 ml) was added dropwise to stirred solution at room temperature. The dropping funnel was washed with anhydrous THF (50 ml) and the mixture was stirred for 1 hour at the same temperature. The formation of thick suspension of lambda/-(2-thenoyl)-1- aminocyclopetanecarboxamide was observed. The water solution of NaOH (12 g, 0.3 mol in 20 ml) and methanol (50 ml) was added and the mixture was heated to reflux for 3 hours. The mixture of organic solvents was removed under reduced pressure and 50 ml of water was added and the product was extracted with EtOAc (5 x 100 ml). The combined organic phases were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 20.4 g (93 %) of 2-(2-thienyl)-1 ,3-diazaspiro[4.4]non-1- en-4-one as a white solid.M.p.: 200 - 202 0C. 1H NMR (CDCI3 ): delta = 1.9-2.0 (m, 8H, CH2 ), 7.1-7.2 (m, 1 H, CH), 7.53 (d, 2H, CH) ppm. 13C NMR (CDCI3): delta = 26.5, 37.8, 79.2, 128.1 , 129.6, 130.2, 132.6, 152.9, 190.5 ppm. HR-MS: 221.0748 (MH+, calc. for C11H13N2OS+: 221.0749).

Reference： [1]Patent: WO2009/149734,2009,A1 .Location in patent: Page/Page column 12

24
[ 1121-60-4 ]
[ 17193-28-1 ]
[ 1262305-05-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 1356 - 1360

25
[ 110-62-3 ]
[ 17193-28-1 ]
[ 151257-03-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 1356 - 1360

26
[ 17193-28-1 ]
[ 555-16-8 ]
[ 1262305-03-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 1356 - 1360

27
[ 17193-28-1 ]
[ 100-52-7 ]
[ 1262305-01-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 1356 - 1360

28
[ 17193-28-1 ]
[ 123-11-5 ]
[ 1262305-02-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 1356 - 1360

29
[ 17193-28-1 ]
[ 90-02-8 ]
[ 1262305-04-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 1356 - 1360

30
[ 15761-39-4 ]
[ 17193-28-1 ]
[ 1291096-42-8 ]

Yield	Reaction Conditions	Operation in experiment
81%		General procedure: To a solution of protected proline (10 mmol) and triethylamine (1.40 ml; 10 mmol) in dry DCM (30 ml), ethyl chloroformate was added dropwise (0.95 ml; 10 mmol) in dry DCM (10 ml). After 30 min, aminoamide (10 mmol) in dry DCM (10 ml) was added to the mixture and the solution was stirred for 5 h. The organic layer was washed with water and aqueous sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue was crystallised from the appropriate solvents.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

31
[ 17193-28-1 ]
[ 1291096-45-1 ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

32
[ 17193-28-1 ]
[ 1291096-46-2 ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

33
[ 17193-28-1 ]
[ 1291096-47-3 ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

34
[ 17193-28-1 ]
[ 1291096-51-9 ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

35
[ 17193-28-1 ]
2-(pyrrolidin-2-yl)-1,3-diazaspiro[4.4]non-1-en-4-one bis(trifluoroacetate) [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

36
[ 17193-28-1 ]
2C₂⁽²⁾HF₃O₂*C₁₁H₁₄⁽²⁾H₃N₃O [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

37
[ 17193-28-1 ]
2-(pyrrolidin-2-yl)-1,3-diazaspiro[4.4]non-1-en-4-one [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

38
[ 17193-28-1 ]
[ 1291096-59-7 ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

39
[ 17193-28-1 ]
[ 69610-41-9 ]
[ 1291096-49-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With acetic acid; In methanol; for 18h;Reflux;	General procedure: A mixture of <strong>[17193-28-1]1-aminocyclopentancarboxamide</strong> or (S)-2-amino-2,3-dimethylbutanamide (10 mmol) and (S)-N-Boc-prolinal (2.19 g; 11 mmol) in 30 ml methanol with one drop of acetic acid was refluxed for 18 h. The solvent was evaporated under reduced pressure and the residue was crystallised from cyclohexane.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

40
[ 17193-28-1 ]
[ 31795-93-4 ]
[ 1291096-44-0 ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: To a solution of protected proline (10 mmol) and triethylamine (1.40 ml; 10 mmol) in dry DCM (30 ml), ethyl chloroformate was added dropwise (0.95 ml; 10 mmol) in dry DCM (10 ml). After 30 min, aminoamide (10 mmol) in dry DCM (10 ml) was added to the mixture and the solution was stirred for 5 h. The organic layer was washed with water and aqueous sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue was crystallised from the appropriate solvents.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

41
[ 17193-28-1 ]
[ 1148-11-4 ]
[ 1291096-47-3 ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

42
[ 17193-28-1 ]
[ 1148-11-4 ]
[ 1291096-40-6 ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: To a solution of protected proline (10 mmol) and triethylamine (1.40 ml; 10 mmol) in dry DCM (30 ml), ethyl chloroformate was added dropwise (0.95 ml; 10 mmol) in dry DCM (10 ml). After 30 min, aminoamide (10 mmol) in dry DCM (10 ml) was added to the mixture and the solution was stirred for 5 h. The organic layer was washed with water and aqueous sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue was crystallised from the appropriate solvents.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 215 - 221

43
[ 17193-28-1 ]
[ 1579511-77-5 ]

Reference： [1]Patent: WO2014/39769,2014,A1
[2]Patent: US2015/99730,2015,A1

44
[ 17193-28-1 ]
[ 1579511-80-0 ]

Reference： [1]Patent: WO2014/39769,2014,A1
[2]Patent: US2015/99730,2015,A1

45
[ 17193-28-1 ]
[ 1579514-36-5 ]

Reference： [1]Patent: WO2014/39769,2014,A1
[2]Patent: US2015/99730,2015,A1

46
[ 17193-28-1 ]
[ 1579511-85-5 ]

Reference： [1]Patent: WO2014/39769,2014,A1

47
[ 17193-28-1 ]
[ 1579511-89-9 ]

Reference： [1]Patent: WO2014/39769,2014,A1
[2]Patent: US2015/99730,2015,A1

48
[ 17193-28-1 ]
[ 1579511-70-8 ]

Reference： [1]Patent: WO2014/39769,2014,A1
[2]Patent: US2015/99730,2015,A1

49
[ 17193-28-1 ]
[ 1579515-66-4 ]

Reference： [1]Patent: WO2014/39769,2014,A1
[2]Patent: US2015/99730,2015,A1

50
[ 17193-28-1 ]
(R)-2-(4-(benzofuran-5-yl)phenyl)-3-(pyrrolidin-3-ylmethyl)-1,3-diazaspiro[4.4]non-1-en-4-one trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2014/39769,2014,A1

51
[ 17193-28-1 ]
[ 1579515-64-2 ]

Reference： [1]Patent: WO2014/39769,2014,A1
[2]Patent: US2015/99730,2015,A1

52
[ 586-76-5 ]
[ 17193-28-1 ]
[ 1579511-74-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;	STEP A: 4-Bromo-N-(1 -carbamoylcvclopentyl)benzamide A mixture <strong>[17193-28-1]1-aminocyclopentanecarboxamide</strong> (0.5 g, 3.9 mmol), 4- bromobenzoic acid (0.784 g, 3.9 mmol), EDCI (0.747 g, 3.9 mmol), HOBt (0.527 g, 3.9 mmol) and DIEA (0.67 mL, 3.9 mmol) in DMF (10 mL) was stirred at room temperature for 1 day. The reaction mixture was partitioned between EtOAc and aqueous saturated NaHC03. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated in vacuo to yield 4-bromo- N-(1 -carbamoylcyclopentyl)benzamide (1 .2 g, 99%). 1 H NMR (400 MHz, DMSO-d6) delta ppm 1 .54 - 1 .82 (m, 3 H), 1 .89 - 2.04 (m, 2 H), 2.04 - 2.23 (m, 2 H), 6.76 (br. s., 1 H), 7.09 (br. s., 1 H), 7.66 (d, J=8.6 Hz, 2 H), 7.83 (d, J=8.6 Hz, 2 H), 8.36 (s, 1 H); MS m/z 313.0 (M+H)+.
99%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;	STEP A: 4-Bromo-N-(1-carbamoylcyclopentyl)benzamide A mixture <strong>[17193-28-1]1-aminocyclopentanecarboxamide</strong> (0.5 g, 3.9 mmol), 4-bromobenzoic acid (0.784 g, 3.9 mmol), EDCI (0.747 g, 3.9 mmol), HOBt (0.527 g, 3.9 mmol) and DIEA (0.67 mL, 3.9 mmol) in DMF (10 mL) was stirred at room temperature for 1 day. The reaction mixture was partitioned between EtOAc and aqueous saturated NaHCO3. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to yield 4-bromo-N-(1-carbamoylcyclopentyl)benzamide (1.2 g, 99%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.54-1.82 (m, 3H), 1.89-2.04 (m, 2H), 2.04-2.23 (m, 2H), 6.76 (br. s., 1H), 7.09 (br. s., 1H), 7.66 (d, J=8.6 Hz, 2H), 7.83 (d, J=8.6 Hz, 2H), 8.36 (s, 1H); MS m/z 313.0 (M+H)+.

Reference： [1]Patent: WO2014/39769,2014,A1 .Location in patent: Page/Page column 241; 242
[2]Patent: US2015/99730,2015,A1 .Location in patent: Paragraph 0670; 0671

53
[ 1610955-32-2 ]
[ 17193-28-1 ]
[ 1610955-36-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With N-ethyl-N,N-diisopropylamine; HATU; In acetonitrile; at 20℃;	6.19. Preparation of l-(4-(4-(2-nnet yl-5-((2S.3R.4R.5S.6R)-3.4.5-tririvdroxy-6- (met yltriio)tetra vdro-2H-pyran-2- yl)benzyl)prienoxy)butanannido)cvclopentanecarboxamide (41) 4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2- yl)benzyl)phenoxy)butanoic acid (39, 46 mg, 0.10 mmol), <strong>[17193-28-1]1-aminocyclopentanecarboxamide</strong> (26 mg, 0.20 mmol), HATU (57 mg, 0.15 mmol), and DIPEA (52 muIota_, 0.30 mmol) were combined in DMF (0.5 ml_) and stirred overnight at room temperature. The reaction was diluted with EtOAc, washed with saturated aqueous NaHC03 and brine (with back extraction), dried over MgS04, filtered, and concentrated under vacuum. The material was purified by prep HPLC (C18 30 x 100 mm column, 20-60% CH3CN /10 mM aqueous ammonium formate, 45 mL/min) and lyophilized to give 35 mg (61% yield) of amide 41 as a white solid. W NMR (400 MHz, MeOH-d4) delta ppm 7.10 - 7.19 (m, 3 H), 7.04 (d, J=8.6 Hz, 2 H), 6.81 (m, J=8.6 Hz, 2 H), 4.39 (d, J=9.3 Hz, 1 H), 4.12 (d, J=9.1 Hz, 1 H), 3.96 (t, J=6.2 Hz, 2 H), 3.92 (s, 2 H), 3.34 - 3.50 (m, 3 H), 2.41 (t, J=7.5 Hz, 2 H), 2.12 - 2.22 (m, 8 H), 2.04 (quin, J=6.9 Hz, 2 H), 1.93 (dt, J=12.8, 5.1 Hz, 2 H), 1.64 - 1.75 (m, 4 H); MS (ES+) [M+H]+ = 573.

Reference： [1]Patent: WO2014/81660,2014,A1 .Location in patent: Page/Page column 38

54
[ 1610955-45-7 ]
[ 17193-28-1 ]
[ 1610955-54-8 ]

Yield	Reaction Conditions	Operation in experiment
		6.27. Preparation of l-(f2-(4-(2-nnetriyl-5-(f2S.3R.4R.5S.6R)-3.4.5-tririvdroxy-6- (methylthio)tetrahvdro-2H-pyran-2- yl)benzyl)phenoxy)ethyl)amino)cvclopentanecarboxamide (52) The same procedure was employed as for amine 50, using 1- aminocyclopentanecarboxamide, to provide the product 52. ^ NMR (400 MHz, MeOH-d4) delta ppm 7.11 - 7.21 (m, 3 H), 7.06 (d, J=8.3 Hz, 2 H), 6.85 (m, J=8.6 Hz, 2 H), 4.39 (d, J=9.6 Hz, 1 H), 4.12 (d, J=9.3 Hz, 1 H), 4.06 (t, J=4.9 Hz, 2 H), 3.94 (s, 2 H), 3.34 - 3.54 (m, 3 H), 2.92 (t, J=4.8 Hz, 2 H), 2.20 (s, 3 H), 2.14 (s, 3 H), 2.06 - 2.13 (m, 2 H), 1.75 - 1.83 (m, 6 H); MS (ES+) [M+H]+ = 531.

Reference： [1]Patent: WO2014/81660,2014,A1 .Location in patent: Page/Page column 44

55
[ 17193-28-1 ]
(R)-2-(4-(benzofuran-5-yl)phenyl)-3-(pyrrolidin-3-ylmethyl)-1,3-diazaspiro[4.4]non-1-en-4-one trifluoroacetate [ No CAS ]

Reference： [1]Patent: US2015/99730,2015,A1

56
[ 17193-28-1 ]
[ 1579515-80-2 ]

Reference： [1]Patent: US2015/99730,2015,A1

57
[ 17193-28-1 ]
(R)-2-(4-bromophenyl)-3-(pyrrolidin-3-ylmethyl)-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride salt [ No CAS ]

Reference： [1]Patent: US2015/99730,2015,A1

58
[ 17193-28-1 ]
[ 5062-66-8 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 740 - 743

59
[ 17193-28-1 ]
4-methyl-N-((1-((4-methylphenyl)sulfonamido)cyclopentyl)methyl)benzenesulfonamide [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 740 - 743

60
[ 17193-28-1 ]
8-methylene-6,9-ditosyl-6,9-diazaspiro[4.5]decane [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 740 - 743

61
[ 17193-28-1 ]
3-((1-(2-(1H-tetrazol-5-yl)phenyl)-1H-indol-4-yl)methyl)-2-propyl-1,3-diazaspiro[4.4]non-1-en-4-one [ No CAS ]