[ CAS No. 324579-90-0 ] {[proInfo.proName]}

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Quality Control of [ 324579-90-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 324579-90-0 ]

SDS Specification

Alternatived Products of [ 324579-90-0 ]

Product Details of [ 324579-90-0 ]

CAS No. :	324579-90-0	MDL No. :	MFCD01571854
Formula :	C₆H₈N₂S	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	FGPNVCRMNYEMEP-UHFFFAOYSA-N
M.W :	140.21	Pubchem ID :	674456
Synonyms :

Calculated chemistry of [ 324579-90-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.98
TPSA :	67.15 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) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.46
Log Po/w (XLOGP3) :	1.18
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	0.59
Log Po/w (SILICOS-IT) :	2.44
Consensus Log Po/w :	1.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.8
Solubility :	2.23 mg/ml ; 0.0159 mol/l
Class :	Very soluble
Log S (Ali) :	-2.19
Solubility :	0.914 mg/ml ; 0.00652 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.51
Solubility :	4.36 mg/ml ; 0.0311 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.34

Safety of [ 324579-90-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 324579-90-0 ]

* 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.

Upstream synthesis route of [ 324579-90-0 ]
Downstream synthetic route of [ 324579-90-0 ]

[ 324579-90-0 ] Synthesis Path-Upstream 1~3

1
[ 69267-75-0 ]
[ 17356-08-0 ]
[ 324579-90-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	Heating / reflux	EXAMPLE N; 4-Cyclopropyl-thiazol-2-ylamine; A solution of 2-Bromo-1-cyclopropyl-ethanone (CAS [69267-75-0], Indian J. Chem. Sect. B, 22(9), 841(1983) (1 g, 6.1 mmol) and thiourea (0.481 g, 6.1 mmol) in 15 ml of methanol was refluxed overnight. The solvent was evaporated off and the title compound was obtained as an off-white solid (1.38 g, 100percent).
100%	Heating / reflux	The 4-Cyclopropyl-thiazol-2-ylamine used in the above example was synthesised according to the following procedure: A solution of 2-Bromo-1-cyclopropyl-ethanone (CAS [69267-75-0], Indian J. Chem. Sect. B, 22(9), 841(1983) (1 g, 6.1 mmol) and Thiourea (0.481 g, 6.1 mmol) in 15 ml of methanol was refluxed overnight. The solvent was evaporated off and the title compound was obtained as an off-white solid (1.38 g, 100percent).
11 g	With copper diacetate In ethanol at 80℃; for 1 h;	To a stirred solution of 2-bromo-l-cyclopropyl-ethanone (16 g, 100 mmol) in EtOH (150 mL) was added successively thiourea (8.0 g, 105 mmol) and Cu(OAc)₂ (0.90 g, 5.0 mmol) at room temperature. After the mixture was heated at 80 °C for 1 hour, the solvent was removed under reduced pressure. The residue was neutralized with saturated NaHC0₃ (100 mL) to pH = 8-9, and then DCM (200 mL) was added. The organic layer was separated and the aqueous layer was further extracted with DCM (200 mL x 2). The combined organic layers were washed with sat. NaHC0₃ (100 mL), brine (100 mL) and dried over anhydrous Na₂S0₄. After filtration and concentration, the residue was purified by column chromatography (eluent: EA: PE = 1 :4) to afford the desired product J (1 1 g) as a yellow solid. 1H NMR (CDCl₃-d, 400 MHz): δ ppm 6.06 (s, 1H), 4.86 (br s, 2H), 1.85-1.79 (m, 1H), 0.84-0.74 (m, 4H).

11 g

With copper diacetate In ethanol at 80℃; for 1 h;

To a stirred solution of 2-bromo-1-cyclopropyl-ethanone (16 g, 100 mmol) in EtOH (150 mL) was added successively thiourea (8.0 g, 105 mmol) and Cu(OAc)₂(0.90 g, 5.0 mmol) at room temperature. After the mixture was heated at 80° C. for 1 hour, the solvent was removed under reduced pressure. The residue was neutralized with saturated NaHCO₃(100 mL) to pH=8-9, and then DCM (200 mL) was added. The organic layer was separated and the aqueous layer was further extracted with DCM (200 mL×2). The combined organic layers were washed with sat. NaHCO₃(100 mL), brine (100 mL) and dried over anhydrous Na₂SO₄. After filtration and concentration, the residue was purified by column chromatography (eluent: EA:PE=1:4) to afford the desired product J (11 g) as a yellow solid. ¹H NMR (CDCl₃-d, 400 MHz): δ ppm 6.06 (s, 1H), 4.86 (br s, 2H), 1.85-1.79 (m, 1H), 0.84-0.74 (m, 4H).

Reference： [1] Patent: US2006/160857, 2006, A1, . Location in patent: Page/Page column 56
[2] Patent: US2006/199960, 2006, A1, . Location in patent: Page/Page column 25
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 8, p. 3352 - 3371
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2764 - 2778
[5] Patent: WO2005/110980, 2005, A2, . Location in patent: Page/Page column 95
[6] Patent: WO2014/37480, 2014, A1, . Location in patent: Page/Page column 98; 99
[7] Patent: US2015/31687, 2015, A1, . Location in patent: Paragraph 0333; 0334

2
[ 17356-08-0 ]
[ 324579-90-0 ]

Reference： [1] Patent: WO2006/40520, 2006, A1, . Location in patent: Page/Page column 163-164

3
[ 765-43-5 ]
[ 324579-90-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2764 - 2778

[ 324579-90-0 ] Synthesis Path-Downstream 1~21

Yield	Reaction Conditions	Operation in experiment
67.86%		General procedure: 0C, Methylpentan-2-one (2.003 g, 20 mmol)In methanol was slowly added dropwise a solution of bromine (1 mL, 20 mmol) Reaction at room temperature for 2h.Distilled water was added to the reaction solution and stirring was continued for half an hour.Followed by extraction with ether and water,The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate.The solvent was evaporated under reduced pressure to give a mixture of 1-bromo-4-methylpentan-2-one and 3-bromo-4-methylpentan-The mixture was used directly in the next reaction without further purification.After the reaction mixture was cooled, the solvent was evaporated to dryness under reduced pressure. The residue was dissolved in water and the pH was adjusted to 12, followed by treatment with acetic acid (10 mL). The reaction mixture was cooled to room temperature, Ethyl acetate and water, and the ethyl acetate layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The mixture was purified by column chromatography on silica gel to give 4-methyl-5-isopropylthiazol-2-amine and 4-isobutylthiazol-2-amine.

2
[ 69267-75-0 ]
[ 17356-08-0 ]
[ 324579-90-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	In methanol;Heating / reflux;	EXAMPLE N; 4-Cyclopropyl-thiazol-2-ylamine; A solution of 2-Bromo-1-cyclopropyl-ethanone (CAS [69267-75-0], Indian J. Chem. Sect. B, 22(9), 841(1983) (1 g, 6.1 mmol) and thiourea (0.481 g, 6.1 mmol) in 15 ml of methanol was refluxed overnight. The solvent was evaporated off and the title compound was obtained as an off-white solid (1.38 g, 100percent).
100%	In methanol;Heating / reflux;	The 4-Cyclopropyl-thiazol-2-ylamine used in the above example was synthesised according to the following procedure: A solution of 2-Bromo-1-cyclopropyl-ethanone (CAS [69267-75-0], Indian J. Chem. Sect. B, 22(9), 841(1983) (1 g, 6.1 mmol) and Thiourea (0.481 g, 6.1 mmol) in 15 ml of methanol was refluxed overnight. The solvent was evaporated off and the title compound was obtained as an off-white solid (1.38 g, 100percent).
	In ethanol; at 110℃; for 12h;	A 500 mL flask was charged 2-bromo-1- cyclopropylethanone (32.0 g, 196.0 mmol, 1.0 equiv), 15 g thiourea (196.0 mmol, 1.0 equiv) and 100mL ethanol. The flask was equipped with a reflux condenser, and then placed into a preheated 110 °C bath with stirring for 12 h under dry N2 atmosphere. The reaction solution was cooled and concentrated under reduced pressure. The residue was then dissolved in H20, neutralized with sat. NaHC03 and extracted with Et20. The organics were washed with brine, dried with Na2S04 and concentrated under reduced pressure. Purification of the crude product by flash chromatography (SiO2,5percent MeOH/ CH2Cl2) provided 10.7 g of the desired product (76.1mmol).

11 g	With copper diacetate; In ethanol; at 80℃; for 1h;	To a stirred solution of 2-bromo-l-cyclopropyl-ethanone (16 g, 100 mmol) in EtOH (150 mL) was added successively thiourea (8.0 g, 105 mmol) and Cu(OAc)2 (0.90 g, 5.0 mmol) at room temperature. After the mixture was heated at 80 °C for 1 hour, the solvent was removed under reduced pressure. The residue was neutralized with saturated NaHC03 (100 mL) to pH = 8-9, and then DCM (200 mL) was added. The organic layer was separated and the aqueous layer was further extracted with DCM (200 mL x 2). The combined organic layers were washed with sat. NaHC03 (100 mL), brine (100 mL) and dried over anhydrous Na2S04. After filtration and concentration, the residue was purified by column chromatography (eluent: EA: PE = 1 :4) to afford the desired product J (1 1 g) as a yellow solid. 1H NMR (CDCl3-d, 400 MHz): delta ppm 6.06 (s, 1H), 4.86 (br s, 2H), 1.85-1.79 (m, 1H), 0.84-0.74 (m, 4H).
11 g	With copper diacetate; In ethanol; at 80℃; for 1h;	To a stirred solution of 2-bromo-1-cyclopropyl-ethanone (16 g, 100 mmol) in EtOH (150 mL) was added successively thiourea (8.0 g, 105 mmol) and Cu(OAc)2 (0.90 g, 5.0 mmol) at room temperature. After the mixture was heated at 80° C. for 1 hour, the solvent was removed under reduced pressure. The residue was neutralized with saturated NaHCO3 (100 mL) to pH=8-9, and then DCM (200 mL) was added. The organic layer was separated and the aqueous layer was further extracted with DCM (200 mL×2). The combined organic layers were washed with sat. NaHCO3 (100 mL), brine (100 mL) and dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by column chromatography (eluent: EA:PE=1:4) to afford the desired product J (11 g) as a yellow solid. 1H NMR (CDCl3-d, 400 MHz): delta ppm 6.06 (s, 1H), 4.86 (br s, 2H), 1.85-1.79 (m, 1H), 0.84-0.74 (m, 4H).

Reference： [1]Patent: US2006/160857,2006,A1 .Location in patent: Page/Page column 56
[2]Patent: US2006/199960,2006,A1 .Location in patent: Page/Page column 25
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 3352 - 3371
[4]Journal of Medicinal Chemistry,2015,vol. 58,p. 2764 - 2778
[5]Patent: WO2005/110980,2005,A2 .Location in patent: Page/Page column 95
[6]Patent: WO2014/37480,2014,A1 .Location in patent: Page/Page column 98; 99
[7]Patent: US2015/31687,2015,A1 .Location in patent: Paragraph 0333; 0334

3
[ 324579-90-0 ]
[ 869854-12-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; acetic acid; In acetonitrile; at 0℃; for 1h;	To a solution of 4- cyclopropylthiazol-2-amine (5 g, 35.7 mmol, 1.0 equiv), 6.1 mL AcOH (106.8 mmol, 3 equiv) and 100 mL acetonitrile was added 6.35 g N-bromosuccinimide (35.7 mmol, 1.0 equiv) at 0 C. After stirring for 1 h, the suspension was diluted with saturated NaHC03 and extracted with EtOAc. The organics were washed with brine, dried with Na2S04 and concentrated under reduced pressure. Purification of the residue by flash chromatography (Si02, 20% EtOAc/Hexane) gave 4.12 g of the product as a brown solid (18.8 mmol).
	With N-Bromosuccinimide; In 1-methyl-pyrrolidin-2-one; at 20℃; for 3h;Cooling with ice;	General procedure: To a mixture of 8 (10.0g, 57mmol) and NMP (100mL) was added NBS (10.6g, 60mmol, 1.1equiv.) portionwise on ice water bath, and the whole was stirred on the same bath for 1hr, then at rt for 2hr. To the reaction mixture was added N-methylpiperazine (28.5g, 285mmol, 5.0equiv.) in NMP (20mL) on an ice water bath, and the whole was stirred at 100C for 8hr. To the reaction mixture was added H2O, and the whole was stirred at room temperature for 10min. The precipitate was collected by filtration, washed with H2O and dried in vacuo to give the title compound (12.5g, 45mmol, 80%) as a pale brown powder. 1H NMR (400MHz, CDCl3): delta=2.35 (3H, s), 2.50-2.63 (4H, m), 2.85-2.97 (4H, m), 4.80 (2H, s), 7.21-7.28 (1H, m, overlapped with CHCl3), 7.32-7.42 (2H, m), 8.04-8.14 (2H, m); MS (ESI) m/z 275 [M+H]+.

Reference： [1]Patent: WO2005/110980,2005,A2 .Location in patent: Page/Page column 95
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3775 - 3787

4
[ 17356-08-0 ]
[ 324579-90-0 ]

Yield	Reaction Conditions	Operation in experiment
		The 2-amino-4-cyclopropylthiazole used as a starting material was prepared as follows :-Bromine (1.3 ml) was added to a stirred solution of cyclopropy methyl ketone in methanol (15 ml) that had been cooled to 0°C. The resultant mixture was stirred at ambient temperature for 45 minutes. "Water (30 ml) was added and the mixture was extracted with EPO <DP n="165"/>diethyl ether. The organic phase was dried over magnesium sulphate and evaporated. The residue was dissolved in ethanol (15 ml) and this solution was added dropwise to a stirred suspension of thiourea (3.84 g) in ethanol (25 ml). The resultant mixture was heated to reflux for 1 hour. The mixture was cooled to ambient temperature and the precipitate was isolated and triturated under diethyl ether. The solid so obtained was dissolved in water (30 ml) and the solution was basified by the addition of a concentrated aqueous sodium bicarbonate solution. The solution was extracted with methylene chloride and the organic phase was dried over mafgnesium sulphate and evaporated. There was thus obtained the required starting material (2 g); 1HNMR: (CDCl3) 0.78 (m, 2H), 0.84 (m, 2H), 1.83 (m, IH), 5.05 (br s, 2H), 6.06 (s, IH); Mass Spectrum: M+H* 141.

Reference： [1]Patent: WO2006/40520,2006,A1 .Location in patent: Page/Page column 163-164

5
[ 324579-90-0 ]
2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid [ No CAS ]
[ 1218791-55-9 ]

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

6
[ 324579-90-0 ]
[ 1095010-50-6 ]

Yield	Reaction Conditions	Operation in experiment
43%	With tert.-butylnitrite; copper(I) bromide; In acetonitrile; at 0 - 20℃; for 0.5h;	To a stirred solution of Compound J (5.6 g, 40 mmol) and CuBr (8.5 g, 60 mmol) in CH3CN (100 mL) was added dropwise t-BuONO (6.2 g, 7.2 mL, 60 mmol) at 0 °C. Then the reaction mixture was warmed to room temperature and further stirred for additional 30 mins. After that, the precipitate was filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography (eluent: 100percent petroleum ether) to afford the desired product K (3.5 g, 43 percent) as a light yellow oil containing small amount of petroleum ether. 1H NMR (400 MHz, CDC13): delta 6.77 (s, 1H), 2.00-1.95 (m, 1H), 0.94-0.85 (m, 4H).
43%	With acetonitrile; copper(I) bromide; sodium t-butanolate; at 0 - 20℃; for 0.5h;	To a stirred solution of Compound J (5.6 g, 40 mmol) and CuBr (8.5 g, 60 mmol) in CH3CN (100 mL) was added dropwise t-BuONO (6.2 g, 7.2 mL, 60 mmol) at 0° C. Then the reaction mixture was warmed to room temperature and further stirred for additional 30 mins. After that, the precipitate was filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography (eluent: 100percent petroleum ether) to afford the desired product K (3.5 g, 43percent) as a light yellow oil containing small amount of petroleum ether. 1H NMR (400 MHz, CDCl3): delta 6.77 (s, 1H), 2.00-1.95 (m, 1H), 0.94-0.85 (m, 4H).

Reference： [1]Patent: WO2014/37480,2014,A1 .Location in patent: Page/Page column 99
[2]Patent: US2015/31687,2015,A1 .Location in patent: Paragraph 0333; 0335
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 3352 - 3371

7
[ 324579-90-0 ]
[ 1378765-88-8 ]

Reference： [1]Patent: WO2014/37480,2014,A1
[2]Patent: US2015/31687,2015,A1
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 3352 - 3371

8
[ 324579-90-0 ]
4-(5-chloro-3-cyclopropylimidazo[2,1-b]thiazole-6-carbonyl)-1-(trans-4-((triisopropylsilyl)oxy)cyclohexyl)piperazin-2-one [ No CAS ]