53051-97-1|2-Amino-5,6-dihydro-4H-cyclopenta[d]thiazole| Ambeed

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Quality Control of [ 53051-97-1 ] Purity: 95% SDS Specification

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Product Details of [ 53051-97-1 ]

CAS No. :	53051-97-1
Formula :	C₆H₈N₂S
M.W :	140.21
SMILES Code :	NC1=NC2=C(CCC2)S1
MDL No. :	MFCD00159774
InChI Key :	HUKBELGUWQLEFD-UHFFFAOYSA-N
Pubchem ID :	332255

Safety of [ 53051-97-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 53051-97-1 ]

* 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.

Downstream synthetic route of [ 53051-97-1 ]

[ 53051-97-1 ] Synthesis Path-Downstream 1~35

1
[ 53051-97-1 ]
[ 2131-55-7 ]
[ 108898-74-4 ]

References: [1]Journal of Organic Chemistry,1958,vol. 23,p. 114.

2
[ 53051-97-1 ]
[ 74-88-4 ]
2-amino-3-methyl-5,6-dihydro-4<i>H</i>-cyclopentathiazolium; iodide [ No CAS ]

References: [1]Journal of the American Chemical Society,1957,vol. 79,p. 5263,5268.

3
[ 694-28-0 ]
[ 17356-08-0 ]
[ 53051-97-1 ]

Yield	Reaction Conditions	Operation in experiment
51.93%	In ethanol; at 80℃; for 12h;	Method 1, 2-Chlorocyclopentanone (2.372 g, 20 mmol)And thiourea (1.523 g, 20 mmol)Was dissolved in ethanol (30 mL)After heating to 80 C,Reflux reaction 12h,After the reaction solution was cooled to room temperature,The resulting white precipitate was filtered,And washed with cold absolute ethanol,After drying in vacuo, the off-white product was 1.835 g,Yield: 51.93%,
	In tetrahydrofuran; ethanol; for 16h;Heating / reflux;	A mixture of 2-chlorocyclopentanone (11.8 g, 100 mmol) and thiourea (8.0 g 101 mmol) was refluxed in ethanol:THF (1:2) for 16 hrs. The reaction mixture was cooled to room temperature and the separated white solid was filtered (9.0 g separated). The white solid was dissolved in anhydrous ethanol (100 ml) and sodium methoxide (2.7 g, 51 mmol) was added. After 15 minutes, ethyl bromopyruvate (10.0 g) was added to the solution, stirred at room temperature for 2 hrs, and then refluxed for 48 hrs. The reaction mixture was cooled to room temperature and concentrated. The residue was extracted with chloroform and washed well with water, and concentrated. The product was purified by silica-gel column chromatography by eluding it with 50% ethyl acetate:hexane. Red semi-solid; Yield: 3.0 g; M+H 237. The ester was reduced with LiAlH4 and the resultant alcohol was oxidized with active MnO2. The aldehyde obtained was taken to the next step.

References: [1]Patent: CN105985356,2016,A .Location in patent: Paragraph 0203; 0204; 0205; 0206.
[2]Chemische Berichte,1960,vol. 93,p. 1518 - 1525.
[3]Helvetica Chimica Acta, Engi-Festband <1941> 172, 177,.
[4]Journal of Medicinal Chemistry,2004,vol. 47,p. 6556 - 6568.
[5]Patent: US2007/27130,2007,A1 .Location in patent: Page/Page column 19.

6
[ 17356-08-0 ]
[ 120-92-3 ]
[ 53051-97-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With iodine; at 110℃; for 12h;Sealed tube;	General procedure: A mixture of ketone (11a or 11b) (10.0 mmol,1.0 equiv), thiourea(20.0 mmol, 2.0 equiv) and iodine (10.0 mmol,1.0 equiv)was stirredin sealed tube at 110 C for 12 h. The reaction mixturewas cooled toroom temperature. Then hot water (10 mL) was added to solubilizethe crude material, and the resulting solutionwas stirred for further30 min. The mixture was allowed to cool to room temperature, andthe water layer was washed with diethyl ether. The aqueous layerwas separated and was neutralized by the careful addition of solidsodium bicarbonate. The aqueous layer was extracted with trichloromethane.And the organic layer was washed with brine,dried over anhydrous sodium sulfate, and concentrated in vacuum.The resulting residue was purified by silica gel chromatography(dichloromethane/methanol 1% aqueous ammonia, v/v, 99:1 to98:2) to give the desired product. 5,6-Dihydro-4H-cyclopenta[d]thiazol-2-amine (12a). This titlecompound was obtained by condensation of cyclopentanone withthiourea according to general procedure A. Brown solid (60%), mp92e93 C. 1H NMR (300 MHz, DMSO-d6) d 5.08 (s, 2H), 2.78e2.70(m, 2H), 2.68e2.58 (m, 2H), 2.42e2.30 (m, 2H). MS (ESI)m/z: 141.0[MH].
25.16%		france two, room temperature to the cyclopentanone (1.0eq) is slowly added in a DMSO solution NBS (1.05eq), reaction at room temperature 20 minutes, then adding 10% ammonium chloride solution, stirring and a half hours and water extraction with ethyl acetate, ethyl acetate layer water and saturated salt water washing, drying of anhydrous magnesium sulfate, concentrated under reduced pressure to get the bombycinous. The bombycinous with thiourea (1.0eq) after the soluble in ethanol, the temperature is increased to 80 C reflux reaction 12h, cooling to be reacted after concentrating under reduced pressure, the residual oily substance soluble in water with 10% sodium hydroxide solution to adjust the pH=12, then with ethyl acetate and water extraction, ethyl acetate layer water and saturated salt water washing, drying by anhydrous magnesium sulphate, silica gel column chromatography purification to obtain after mixes the type 5,6-dihydro -4H-cyclopenta [d] thiazol-2-amine. Yield: 25.16%

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 128 - 152.
[2]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 634 - 637.
[3]Patent: CN105985356,2016,A .Location in patent: Paragraph 0203; 0204; 0207; 0208.

7
[ 53051-97-1 ]
[ 70-23-5 ]
[ 349481-42-1 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 2-chlorocyclopentanone (11.8 g, 100 mmol) and thiourea (8.0 g 101 mmol) was refluxed in ethanol:THF (1:2) for 16 hrs. The reaction mixture was cooled to room temperature and the separated white solid was filtered (9.0 g separated). The white solid was dissolved in anhydrous ethanol (100 ml) and sodium methoxide (2.7 g, 51 mmol) was added. After 15 minutes, ethyl bromopyruvate (10.0 g) was added to the solution, stirred at room temperature for 2 hrs, and then refluxed for 48 hrs. The reaction mixture was cooled to room temperature and concentrated. The residue was extracted with chloroform and washed well with water, and concentrated. The product was purified by silica-gel column chromatography by eluding it with 50% ethyl acetate:hexane. Red semi-solid; Yield: 3.0 g; M+H 237. The ester was reduced with LiAlH4 and the resultant alcohol was oxidized with active MnO2. The aldehyde obtained was taken to the next step.

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2764 - 2778.
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 6556 - 6568.
[3]Patent: US2007/27130,2007,A1 .Location in patent: Page/Page column 19.

8
[ 15781-73-4 ]
[ 53051-97-1 ]
C₁₅H₁₂N₂O₂S [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 8250 - 8252.

9
[ 53051-97-1 ]
[ 623906-29-6 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6556 - 6568.

10
[ 53051-97-1 ]
(5R),(6Z)-6-(6,7-dihydro-5H-cyclopenta[d]imidazo[2,1-b][1,3]thiazol-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6556 - 6568.

11
[ 53051-97-1 ]
[ 349481-43-2 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6556 - 6568.

12
[ 53051-97-1 ]
[ 623906-28-5 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6556 - 6568.

13
[ 53051-97-1 ]
[ 74370-98-2 ]
N-(5,6-Dihydro-4H-cyclopentathiazole-2-yl)-4-hydroxy-2-methyl-2H-[1] benzothieno [2,3-e]-1,2-thiazine-3-carboxamide-1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		EXAMPLE 18 N-(5,6-Dihydro-4H-cyclopentathiazole-2-yl)-4-hydroxy-2-methyl-2H-[1] benzothieno [2,3-e]-1,2-thiazine-3-carboxamide-1,1-dioxide Prepared analogous to Example 1 from methyl 4-hydroxy-2-methyl-2H-[1] benzothieno [2,3-e]-1,2-thiazine-3-carboxylate-1,1-dioxide and 5,6-dihydro-4H-cyclopentathiazole-2-amine with a yield of 57% of theory. M.p.: 258-259 C. (decomp.) after recrystallization from dimethylformamide. C18 H15 N3 O4 S3 (433.53): Calc.: C-49.87%; H-3.49%; N-9.69%; S-22.19%; Found: C-49.30%; H-3.51%; N-9.69%; S-21.85%

References: [1]Patent: US4259336,1981,A .

14
[ 53051-97-1 ]
[ 75271-94-2 ]
[ 623906-29-6 ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium hydrogencarbonate; In isopropyl alcohol; at 0 - 40℃; for 24.5h;	Example 1 6,7-Dihydro-5H-cyclopenta[d]imidazo[2,1-b]thiazole-2-carbaldehyde (1): A solution of 5,6-dihydro-4H-cyclopentathiazol-2-ylamine (2) (200 g free base, 1.43 mol) in 2-propanol (1 L) was added over 30 minutes to a stirred, cooled (0-5 C.) suspension of bromopyruvaldehyde dimethylacetal 3 (530 g, 2.75 mol), sodium bicarbonate (55 g, 0.66 mol), and 2-propanol (0.30 L). The mixture was allowed to stir for 16 h. The mixture was warmed to 40 C. for 8 h, and was concentrated under reduced pressure to provide a red residue. The red residue was added to methyl t-butyl ether (2.0 L). The mixture was stirred for a minimum of 1 h. The solid was collected by filtration and washed with Et2O. The dried solid (550 g) was dissolved in methylene chloride (2.75 L). The methylene chloride mixture was passed through a pad of silica gel (1.65 kg). The pad was washed with methylene chloride and 10% EtOAc/methylene chloride. The filtrate was concentrated to a yellow solid, which was triturated with Et2O and collected by filtration to give 81 g (30%) of the title compound. 1H NMR (CDCl3) delta 9.93 (1H, s), 7.91 (1H, s), 2.99-2.89 (4H, m), 2.62-2.57 (2H, m).

References: [1]Patent: US2007/149499,2007,A1 .Location in patent: Page/Page column 9-10; 18.

15
[ 82514-58-7 ]
[ 53051-97-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydrogencarbonate; In tetrahydrofuran; water; ethyl acetate; at 20℃; for 0.25h;	Example 4; 5,6-Dihydro-4H-cyclopentathiazol-2-ylamine (2), free base: The hydrochloride salt of 2 (16.5 g, 93 mmol) (for synthesis of HCl salt, see, e.g., Erlenmeyer and Scheonauer, Helv. Chim. Acta, vol. 24, p. 172E and 175 (1941) and Huenig et al., Chem. Ber., vol. 93, p. 1518-1525 (1960)) was added to a mixture of aqueous sodium bicarbonate (16.5 g, 250 mL) and 25% THF/EtOAc (160 mL, v/v). The mixture was stirred at room temperature for 15 min. The mixture was clarified by filtration through a pad of celite. The organic layer was separated, dried (MgSO4), and concentrated in vacuo to 47 g. Toluene (100 mL) was added and the mixture was concentrated in vacuo to 45 g. The mixture was diluted with heptane (40 mL), cooled, and the product was collected by filtration and dried to give the title compound as the free base (10.75 g, 85%). 1H NMR (CD3OD) delta 4.88 (2H, s), 2.75-2.70 (2H, m), 2.60-2.55 (2H, m), 2.39-2.33 (2H, m).

References: [1]Patent: US2007/149499,2007,A1 .Location in patent: Page/Page column 19.

16
[ 53051-97-1 ]
[ 201006-49-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylnitrite; copper(l) chloride; In acetonitrile; at 20 - 65℃; for 3h;	2-Amino-5,6-dihydro-4H-cyclopentathiazole (230 mg, 1.64 mmol) was added to a solution of cupric chloride (260 mg, 1.97 mmol) and ferf-butylnitrite (0.3 ml, 2.46 mmol) in MeCN (0.5 ml) and the resulting mixture was stirred for 2 h at room temperature, then at 650C for 1 h. The reaction was filtered and the filtrate partitioned between water and EtOAc. The organic fraction was dried (MgSO4), filtered and concentrated under reduced pressure to give the chloride (140 mg), which was used without further purification. MS: [M+H]+ = 160.

References: [1]Patent: WO2009/150240,2009,A1 .Location in patent: Page/Page column 121.

17
[ 53051-97-1 ]
2-[4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionic acid [ No CAS ]
[ 1236286-00-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3875 - 3884.

18
[ 930-30-3 ]
[ 17356-08-0 ]
[ 53051-97-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	With iodine; at 100℃;	A mixture of cyclopentanone (8.4 g, 0.1 mol), thiourea (15.22 g, 0.2 mol) and iodine (25.38 g, 0.1 mol) was heated overnight at 100 C., then isopropyl ether was added and the mixture heated at reflux for an additional 30 minutes. The solid was collected via filtration, washed with ether, and then dissolved in hot water. The solution was left to cool to RT, was then basified with concentrated ammonia, and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give the desired product (5.56 g 40% yield). ESIMS (m/z) 141.0 (MH+).

References: [1]Patent: US2010/227859,2010,A1 .Location in patent: Page/Page column 86-87.

19
[ 53051-97-1 ]
[ 1080642-17-6 ]