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Quality Control of [ 30235-28-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 30235-28-0 ]

SDS Specification

Alternatived Products of [ 30235-28-0 ]

Product Details of [ 30235-28-0 ]

CAS No. :	30235-28-0	MDL No. :	MFCD00490009
Formula :	C₈H₇N₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CUSJGENRTWNHPV-UHFFFAOYSA-N
M.W :	177.23	Pubchem ID :	930237
Synonyms :

Calculated chemistry of [ 30235-28-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	49.75
TPSA :	80.04 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.37
Log Po/w (XLOGP3) :	1.2
Log Po/w (WLOGP) :	1.8
Log Po/w (MLOGP) :	0.13
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	1.39

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	0.874 mg/ml ; 0.00493 mol/l
Class :	Soluble
Log S (Ali) :	-2.48
Solubility :	0.591 mg/ml ; 0.00333 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.08
Solubility :	0.148 mg/ml ; 0.000838 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.08

Safety of [ 30235-28-0 ]

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

Application In Synthesis of [ 30235-28-0 ]

* 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.

Downstream synthetic route of [ 30235-28-0 ]

[ 30235-28-0 ] Synthesis Path-Downstream 1~23

1
[ 1122-54-9 ]
[ 17356-08-0 ]
[ 30235-28-0 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 22,35

2
2-amino-4-[4]pyridyl-thiazole-5-carboxylic acid ethyl ester; hydrochloride [ No CAS ]
[ 30235-28-0 ]

Reference： [1]Zhurnal Obshchei Khimii,1956,vol. 26,p. 1137,1140;engl.Ausg.S.1291,1294

3
[ 53289-47-7 ]
[ 17356-08-0 ]
[ 30235-28-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1976,vol. 318,p. 875 - 877

4
[ 6221-13-2 ]
[ 17356-08-0 ]
[ 30235-28-0 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of 2 (11.2 mmol) in 25 ml of ethanol at room temperature was added thiourea (13.4 mmol).The reaction mixture was stirred at room temperature for 1 hour, quenched with water and washed with dichloromethane. The aqueous phase was concentrated in vacuo to give a yellow solid HBr salt. The salt was then dissolved in minimal amount of water and 10% NaOH added drop wise until a white precipitate 3 formed (approximately at pH 8).The precipitate was then filtered and dried.

Reference： [1]Journal of Heterocyclic Chemistry,1970,vol. 7,p. 1137 - 1141
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 560 - 564
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 5028 - 5037

Yield	Reaction Conditions	Operation in experiment
95%	In ethanol; for 2h;Inert atmosphere; Reflux;	General procedure: A mixture of the substrate (i.e. appropriate bromoketone) (1 eq) and thiourea (1.5 eq) in EtOH (3 mL per 1 mmol of bromoketone, unless stated otherwise) was refluxed for 2 h (unless stated otherwise).
	With potassium carbonate; In ethanol; for 5h;Reflux;	General procedure: Preparation of 4-pyridin-3-yl-thiazol-2-ylamine l-b To a solution of 2-bromo-l-pyridin-3-yl-ethanone Hydrobromide l-a (10 g, 35.58 mmol) in ethanol (100 mL) was added thiourea (2.98 g, 39.21 mmol), K2C03 (9.83 g, 71 .16 mmol) and the reaction mixture was refluxed for 5h. After cooling to room temperature and evaporation of solvent, 150 mL of a saturated solution of NaHC03 was added and reaction mixture was stirred for 1 h. The precipitate was collected by filtration, washed by water and dried under vacuum to give the title compound l-b (6,2 g, 98%). H NMR (400 MHz, DMSO-cfe) H NMR (400 MHz, DMSO-d6) delta 9.01 (d, J = 2.0 Hz, 1 H), 8.45 (dd, J = 4.7, 1 .5 Hz, 1 H), 8.12 (dt, J = 7.9, 1 .9 Hz, 1 H), 7.39 (dd, J = 8.0, 4.8 Hz, 1 H), 7.20 (s, 1 H), 7.19 (s, 2H).

6
[ 30235-28-0 ]
[ 436151-27-8 ]
2-oxo-nonanedioic acid 1-methylamide 9-[(4-pyridin-4-yl-thiazol-2-yl)-amide] [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3331 - 3335

7
[ 30235-28-0 ]
[ 621-37-4 ]
methanesulfonic acid 3-[(4-pyridin-4-yl-thiazol-2-ylcarbamoyl)-methyl]-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-(1-methanesulfonyl) benzotriazole; triethylamine; In tetrahydrofuran; at 160℃; for 0.166667h;Microwave;	Methanesulfonic acid 3- [ (4-PYRIDIN-4-YL-THIAZOL-2-YLCARBAMOYL)-METHYL]- phenyl ester: 4- (4-PYRIDYL)-2-AMINOTHIAZOLE (317 mg, 1.79 MMOL), 3-HYDROXYPHENYLACETIC acid (343 mg, 2.25 mmol) and N- (1-METHANESULFONYL) benzotriazole (927 mg, 4.70 mmol) were placed in a microwave reaction vessel (Personal Chemistry, Uppsala, Sweden). THF (2 mL) was added followed by triethylamine (1.24 mL, 8.93 mmol) and the mixture heated in the sealed tube at 160C for 10 minutes. Upon cooling to room temperature the solvent was concentrated and ethanol added. The mixture was stored at -20C and then the precipitated product was filtered, washed with ethanol and dried. (910 mg, 65%). LH NMR (500 MHz, DMSO-d6) 12.62 (1H, s), 8.63 (2H, d), 7.98 (1H, s), 7.84 (2H, d), 7.47 (1H, m), 7.36 (2H, m), 7.27 (1H, m), 3.89 (2H, s), 3.40 (3H, s). LC-MS Rt = 2.1 min, [M+H] + = 390, [M-H]-= 388.

Reference： [1]Patent: WO2004/41813,2004,A1 .Location in patent: Page 121-122

8
[ 30235-28-0 ]
[ 451-82-1 ]
[ 692870-64-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-(1-methanesulfonyl) benzotriazole; triethylamine; In tetrahydrofuran; at 160℃; for 0.166667h;Microwave;	2- (2-FLUOROPHENYL)-N- (4-PYRIDIN-4-YL-THIAZOL-2-YL)-ACETAMIDE : 4- (4-PYRIDYL)-2- aminothiazole (329 mg, 1.86 mmol), 2-fluorophenylacetic acid (377 mg, 2.25 mmol) and N- (1-methanesulfonyl) benzotriazole (440 mg, 2.23 mmol) were placed in a microwave reaction vessel (Personal Chemistry, Uppsala, Sweden). THF (2 ML) was added followed by triethylamine (0.52 ML, 3.73 mmol) and the mixture heated in the sealed tube at 160 C for 10 minutes. Upon cooling to room temperature the product 2- (2-FLUOROPHENYL)-N- (4-PYRIDIN- 4-yl-thiazol-2-yl) -acetamide precipitated, was filtered, washed with acetonitrile and dried. (462 mg, 76%).'H NMR (500 MHz, DMSO-d6) 6 12.68 (1H, s), 8.63 (2H, d), 8.00 (1H, s), 7.84 (2H, d), 7.43-7. 17 (4H, m), 3.90 (2H, s). LC-MS Rt = 1.9 min, [M+H]+= 314, [M-H]-= 312.

Reference： [1]Patent: WO2004/41813,2004,A1 .Location in patent: Page 121
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5028 - 5037

9
[ 30235-28-0 ]
[ 79-04-9 ]
[ 57332-64-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	In 1,4-dioxane;Heating / reflux;	2-CHLORO-N- (4-PYRIDIN-4-YL-THIAZOL-2-YL)-ACETAMIDE : A solution of 4-pyridin-4- yl-thioazol-2-ylamine (3.64 g, 0.02 mol) and chloroacetyl chloride (3.39 g, 0.03 mol) in dioxane was refluxed overnight then cooled to room temperature. The solid precipitate was filtered, then the filtration cake was suspended in saturated KHC03, then filtered again. The filtration cake was washed with water dried in dessicator over P205. 2-CHLORO-N- (4-PYRIDIN- 4-yl-thiazol-2-yl)-acetamide (4.3 g, 85%).'H NMR (500 MHz, DMSO-d6) 8 4.42 (s, 2H), 7.9 (d, 2H), 8.77 (d, 2H).
	With triethylamine; In tetrahydrofuran; at 0℃; for 2h;	4-(Pyridin-4-yl)thiazol-2-amine (0.025 moles, 4.41 g) andtriethylamine (0.03 mole, 4.21 mL) were dissolved in THFwith constant stirring at 0-5C. Then, chloro-acetyl chloride(0.03 mole, 2.90 mL) was added dropwise gradually to thissolution. The reaction mixture thus obtained was further agitatedfor 2 h at 0C. After the solvent was vaporized to dryness,the solid was washed with water and filtered.

Reference： [1]Patent: WO2004/41813,2004,A1 .Location in patent: Page 126-127
[2]Letters in drug design and discovery,2019,vol. 16,p. 547 - 555

10
[ 30235-28-0 ]
[ 1798-09-0 ]
2-(3-methoxyphenyl)-N-(4-pyridin-4-yl-thiazol-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃;	3- (3-METHOXY-PHENYL)-1- (4-PYRIDIN-4-YL-THIAZOL-2-YL)-PIPERIDIN-2-ONE : 2- (3- METHOXY-PHENYL)-N- (4-PYRIDIN-4-YL-THIAZOL-2-YL)-ACETAMIDE (prepared according to General Method A from 4- (4-PYRIDYL)-2-AMINOTHIAZOLE and 3-methoxyphenylacetic acid: 1 mmol), triphenylphosphine (1.2 mmol), diisopropyl azodicarboxylate (1.2 mmol) and THF were were stirred overnight at room temperature. The mixture was then cooled to 0 C and NaH (1.2 mmol) added and reaction mixture was stirred at 0 C for 30 minutes. MEOH was added to quench the reaction. The solvent was evaporated and the residue dissolved in ethyl acetate and washed with H20 and dried over NA2SO4. The product was purified by flash column chromatography on silica gel to afford 3- (3-methoxyphenyl)-1- (4-pyridin-4-yl-thiazol-2-yl)- piperidin-2-one in 60% YIELD.'H NMR (500 MHz, DMSO-d6) 8 8.67 (d, 2H), 7.80 (d, 2H), 7.46 (s, 1H), 7.30 (m, 1H), 6.85 (m, 3H), 4.57 (m, 1H), 4.32 (m, 1H), 3.93 (m, 1H), 3.82 (s, 3H), 2.36 (m, 1H), 2.25 (m, 1H), 2.15 (m, 2H). LC-MS (10-90% CH3CN in H20), Rt = 2.40 min, [M+H] + = 366, [M-H]-= 364.

Reference： [1]Patent: WO2004/41813,2004,A1 .Location in patent: Page 125; 126
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5028 - 5037

11
4-pyridin-4-yl-thiazol-2-ylamine dihydrobromide [ No CAS ]
[ 30235-28-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With ammonia; In water;	4-PYRIDIN-4-YL-THIAZOL-2-YLAMINE : To 4- (BROMOACETYL)-PYRIDINE hydrobromide (Can. J. Chem. , 1970,7, 1137) (97.5 g, 0.35 mol) and thiourea (26.5 g, 0.35 mol) was added ethanol (900 mL) and the mixture heated to reflux for 2 hours. After cooling to 4 C the product was filtered, washed with ethanol and diethyl ether and dried under suction. The solid 4-pyridin-4-yl-thiazol-2-ylamine dihydrobromide (88.7 g) was dissolved in warm water (500 mL) and the desired 4-PYRIDIN-4-YL-THIAZOL-2-YLAMINE obtained as a light brown solid upon addition of 7% aqueous ammonium hydroxide (800 mL). 43.5 g, 71%. LH NMR (500 MHz, DMSO-d6) 6 8.53 (2H, d), 7.71 (2H, d), 7.38 (1H, s), 7.16 (2H, br).

Reference： [1]Patent: WO2004/41813,2004,A1 .Location in patent: Page 119-120

12
[ 30235-28-0 ]
[ 463-71-8 ]
[ 710351-32-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In acetone; at 0 - 20℃; for 2.5h;	A solution of 1 (1 eq) and sodium carbonate (1.5 eq) in acetone was stirred in an ice bath under an atmosphere of nitrogen. Thiophosgene (1.5 eq) was added drop wise over 30 minutes. The reaction was stirred for another 30 minutes in the ice bath before being removed and allowed to warm to RT. The reaction was stirred at RT for 1.5 h before the reaction solution was concentrated under vacuum. Toluene was added to the crude product and removed under vacuum to azetrope off any residual thiophosgene and afford the product 2. MS: MH+=219

Reference： [1]Patent: US2004/122237,2004,A1 .Location in patent: Page 373

13
[ 6221-13-2 ]
[ 30235-28-0 ]

Yield	Reaction Conditions	Operation in experiment
410 mg (65%)		(B) 4-(4-Pyridyl)-1,3-thiazol-2-amine Reactions were performed in the same manner as in Example 8, (A) by using 2-bromo-1-(4-pyridyl)-1-ethanone (1 g, 3.56 mmol) to obtain 410 mg (65%) of the title compound. 1H-NMR (CD3OD) delta:7.26 (1H, s), 7.80 (2H, d, J=6.35 Hz), 8.50 (2H, d, J=6.35 Hz) EI/MS; m/z: 176 (M+-1)

Reference： [1]Patent: US2003/92720,2003,A1

14
[ 30235-28-0 ]
[ 620-23-5 ]
[ 1187669-22-2 ]

Yield	Reaction Conditions	Operation in experiment
22%		Example 1-657V-(3-Methylbenzyl)-4-(4-pyridinyl)- 1 ,3-thiazol-2-amine (103). [0319] 7V-(3-Methylbenzyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (103). A mixture of 2-aminothiazole 98 (0.31 g, 1.8 mmol) and 3-methylbenzaldehyde (0.25 mL, 2.1 mmol) in THF (20 mL) was stirred at reflux temperature for 4 h. The mixture was cooled to 20 0C and a solution OfNaBH4 (265 mg, 7.0 mmol) in water (4 mL) was added dropwise and the mixture was stirred at 20 0C for 30 min. The mixture was diluted with water (30 mL) and extracted with EtOAc (3 x 25 mL). The combined organic fraction was dried and the solvent evaporated. The crude solid was purified by column chromatography, eluting with a gradient (50-100%) of EtO Ac/pet, ether, to give amine 103 (0.11 g, 22%) as a cream powder: mp (MeOH/EtOAc) 192-194 0C; 1H NMR delta 8.54 (dd, J= 4.5, 1.6 Hz, 2 H, H-2', H- 6'), 8.30 (t, J= 5.8 Hz, 1 H, NH), 7.75 (dd, J= 4.5, 1.6 Hz, 2 H, H-3', H-5'), 7.42 <n="138"/>(s, 1 H, H-5), 7.17-7.24 (m, 3 H, H-2", H-4", H-5"), 7.07 (br d, J= 6.9 Hz, 1 H, H- 6"), 4.48 (d, J= 5.8 Hz, 2 H, CH2N), 2.30 (s, 3 H, CH3); MS m/z 282.5 (MH+, 100%). Anal, calcd for Ci6Hi5N3S-1Z4CH3OH: C, 67.87; H, 5.48; N, 14.72. Found: C, 67.78; H, 5.42; N, 14.92%.

Reference： [1]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 136-137

15
[ 5349-17-7 ]
[ 17356-08-0 ]
[ 30235-28-0 ]

Yield	Reaction Conditions	Operation in experiment
95%		COMPOUND 3a4-(Pyridin-4-yl)thiazol-2-amine. Synthesis of batch 1. A mixture of 4-(bromoacetyl)pyridine hydrobromide (2) (2.21 g, 7.90 mmol), thiourea (0.60 g, 7.90 mmol) in anhydrous EtOH (10 ml) was stirred in a Biotage microwave at 100 C for 30 min. After colling to room temperature, the solid precipitate was filtered, dried under vacuum.Synthesis of batch 2. A mixture of 4-(bromoacetyl)pyridine hydrobromide (2) (2.54 g, 9.06 mmol), thiourea (0.69 g, 9.06 mmol) in anhydrous EtOH (10 ml) was stirred in a Biotage microwave at 100 C for 30 min. After colling to room temperature, the solid precipitate was filtered, dried under vacuum.Synthesis of batch 3. A mixture of 4-(bromoacetyl)pyridine hydrobromide (2) (2.16 g, 7.73 mmol), thiourea (0.58 g, 7.73 mmol) in anhydrous EtOH (10 ml) was stirred in a Biotage microwave at 100 C for 30 min. After colling to room temperature, the solid precipitate was filtered, dried under vacuum.Batches 1, 2, and 3 were combined, suspended in an aqueous sat. solution of NaHC03 , filtered, dried under vacuum to provide the title compound as a pale pink solid (5.53 g, 31.27 mmol, 95%), 1H NMR (400 MHz, CD3OD) delta 8.49 (d, J= 6.3 Hz, 2H), 7.79 (d, J= 6.3 Hz, 2H), 7.25 (s, 1H).
93%		A mixture of 2-bromo-l-pyridin-4-yl-ethanone hydrobromide (10 g, 35.59 mmol) and thiourea (2.71 g, 35.59 mmol) in absolute EtOH (100 mL) was re fluxed overnight. After cooling, the reaction mixture was diluted with water (400 mL), the pH was adjusted to 11 with ammonium hydroxide solution, and it was further stirred for 2h. The resulting precipitate was filtered, washed with water, and dried in vacuo to provide 5.85 g of 4-(2-amino- thiazol-4-yl)-pyridine as a pinkish solid (93% yield): 1H NMR (DMSO-dtf, ppm) delta 7.23 (broad s, 2H), 7.42 (s, 1H), 7.74 (d, 2H), 8.56 (d, 2H); [M+H]+ m/z 178
		Example 1-61N- [4-(4-Pyridinyl)- 1 ,3-thiazol-2-yl] benzamide (99). [0314] 4-(4-Pyridinyl)-l,3-thiazol-2-amine (98). A mixture of bromoketone hydrobromide 1 (5.0 g, 17.8 mmol) and thiourea (1.36 g, 17.8 mmol) in EtOH (100 mL) was stirred at reflux temperature for 2 h. The mixture was cooled to 20 0C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 0 0C for 1 h. The precipitate was filtered, washed with water (5 mL) and ether (5 mL) and dried to give amine 98 (2.70 g, 86%) as a pink powder: mp (EtOH/H2O) 278-282 0C [lit. (Westphal, G. et al, J Prakt. Chemie (Leipzig) 1976, 318, 875) mp (EtOH) 276-277 0C]; 1H NMR delta 8.53 (dd, J= 4.6, 1.6 Hz, 2 H, H-2', H-6'), 7.91 (dd, J= 4.6, 1.6 Hz, 2 H, H-3', H-5'), 7.38 (s, 1 H, H-5), 7.16 (br s, 2 H, NH2); MS m/z 178.3 (MH+, 100%).

Reference： [1]MedChemComm,2012,vol. 3,p. 699 - 709
[2]Patent: WO2011/130740,2011,A2 .Location in patent: Page/Page column 42
[3]Patent: WO2012/125981,2012,A2 .Location in patent: Page/Page column 131
[4]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[5]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 133
[6]RSC Advances,2019,vol. 9,p. 10454 - 10464

16
[ 30235-28-0 ]
[ 100-07-2 ]
[ 393839-09-3 ]

Yield	Reaction Conditions	Operation in experiment
61%	With pyridine; dmap; at 20℃; for 16h;	Example 1-644-Methoxy-7V-[4-(4-pyridinyl)-l,3-thiazol-2-yl]benzamide (102). <n="137"/>[0318] 4-Methoxy-7V-[4-(4-pyridinyl)-l,3-thiazol-2-yl]benzamide (102). 4-Methoxybenzoyl chloride (0.77 mL, 5.5 mmol) was added to a stirred solution of amine 98 (0.89 g, 5.0 mmol) and DMAP (60 mg, 0.5 mmol) in pyridine (30 mL) and the solution stirred at 20 0C for 16 h. The solvent was evaporated and the residue partitioned between water (70 mL) and EtOAc (70 mL). The organic fraction was washed with water (30 mL), dried and the solvent evaporated. The crude solid was purified by column chromatography, eluting with a gradient (0- 10%) of MeOH/DCM, to give benzamide 102 (448 mg, 61%) as a white powder: mp (MeOH/DCM) 271-274 0C; 1H NMR delta 12.66 (s, 1 H, NHCO), 8.63 (dd, J = 4.5, 1.6 Hz, 2 H, H-2", H-6"), 8.15 (ddd, J= 8.9, 2.9, 2.0 Hz, 2 H, H-2, H-6), 8.01 (s, 1 H, H-5'), 7.88 (dd, J= 4.5, 1.6 Hz, 2 H, H-3", H-5"), 7.09 (ddd, J= 8.9, 2.9, 2.0 Hz, 2 H, H-3, H-5), 3.86 (s, 3 H, OCH3); 13C NMR delta 164.6, 162.7, 159.2, 150.1 (2), 146.5, 141.0, 130.2 (2), 123.8, 119.9 (2), 113.8 (2), 112.4, 55.4; MS m/z 312.5 (MH+, 100%). Anal, calcd for Ci6Hi3N3O2S: C, 61.72; H, 4.21; N, 13.50. Found: C, 61.38; H, 4.48, N, 13.41%.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 135-136

17
[ 30235-28-0 ]
[ 98-88-4 ]
[ 476625-88-4 ]

Yield	Reaction Conditions	Operation in experiment
61%	With pyridine; dmap; at 20℃; for 16h;	[0315] TV- [4-(4-Pyridinyl)- 1 ,3-thiazol-2-yl] benzamide (99). Benzoyl chloride (0.44 mL, 3.8 mmol) was added to a stirred solution of amine 98 (0.44 g, 2.5 mmol) and DMAP (30 mg, 0.25 mmol) in pyridine (30 mL) and the solution stirred at 20 0C for 16 h. The solvent was evaporated and the residue partitioned between water (70 mL) and EtOAc (70 mL). The organic fraction was washed with water (30 mL), dried and the solvent evaporated. The crude solid was purified by column chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give benzamide 99 (448 mg, 61%) as a white powder: mp (MeOH/DCM) 241-243 0C; 1H NMR delta 12.84 (s, 1 H, NHCO), 8.64 (dd, J= 4.5, 1.6 Hz, 2 H, H-2", H-6"), 8.14 (br d, J= 7.1 Hz, 2 H, H-2, H-6), 8.04 (s, 1 H, H-5'), 7.90 (dd, J= 4.5, 1.6 Hz, 2 H, H-3", H-5"), 7.56 (tt, J= 7.4, 1.3 Hz, 1 H, H-4), 7.35-7.39 (m, 2 H, H-3, H- 5); 13C NMR delta 165.3, 159.0, 150.1 (2), 146.6, 140.9, 132.6, 131.7, 128.5 (2), 128.1 (2), 119.9 (2), 112.6; MS m/z 282.4 (MH+, 100%). Anal, calcd for CI5HHN3OS: C, 64.04; H, 3.94; N, 14.94. Found: C, 63.75; H, 4.12, N, 14.93%.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 134

18
[ 30235-28-0 ]
[ 1711-06-4 ]
[ 476631-30-8 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 16h;	Example 1-623-Methyl-7V- [4-(4-py ridinyl)-. ,3-thiazol-2-yl] benzamide (100). [0316] 3-Methyl-7V-[4-(4-pyridinyl)-l,3-thiazol-2-yl]benzamide (100). Oxalyl chloride (0.26 mL, 3.0 mmol) was added to a stirred solution of m-toluic acid (0.41 g, 3.0 mmol) and DMF (3 drops) in DCM (30 mL) and the solution stirred at 20 0C for 1 h. A solution of amine 98 (354 mg, 2.0 mmol) was added and the mixture stirred at 20 0C for 16 h. The solvent was evaporated and the residue partitioned between water (70 mL) and EtOAc (70 mL). The organic fraction was washed with water (30 mL), dried and the solvent evapporated. The crude solid was purified by column chromatography, eluting with a gradient (0-10%) of MeOH/EtOAc, to give benzamide 100 (110 mg, 19%) as a cream powder: mp (MeOH/EtOAc) 201- 202 0C; 1H NMR delta 12.77 (br s, 1 H, CONH), 8.64 (dd, J= 4.6, 1.6 Hz, 2 H, H-2", H-6"), 8.05 (s, 1 H, H-5), 7.98 (br s, 1 H, H-2), 7.92 (br d, J= 6.9 Hz, 1 H, H-6), 7.88 (dd, J= 4.6, 1.6 Hz, 2 H, H-3", H-5"), 7.42-7.48 (m, 2 H, H-4, H-5), 2.41 (s, <n="136"/>3 H, CH3); 13C NMR delta 165.4, 159.0, 150.1 (2), 146.5, 140.9, 137.8, 133.1, 131.7, 128.6, 128.3, 125.2, 119.2 (2), 112.5, 20.7; MS m/z 296.4 (MH+, 100%). Anal, calcd for Ci6Hi3N3OS: C, 65.06; H, 4.44; N, 14.23. Found: C, 65.19 H, 4.56; N, 14.31%.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 134-135

19
[ 30235-28-0 ]
[ 874-60-2 ]
[ 476631-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 16h;	Example 1-634-Methyl-7V- [4-(4-py ridinyl)-l ,3-thiazol-2-yl] benzamide (101). [0317] 4-Methyl-7V-[4-(4-pyridinyl)-l,3-thiazol-2-yl]benzamide (101). Oxalyl chloride (0.26 rnL, 3.0 mmol) was added to a stirred solution of/>toluic acid (0.41 g, 3.0 mmol) and DMF (3 drops) in DCM (30 mL) and the solution stirred at 20 0C for 1 h. A solution of amine 98 (354 mg, 2.0 mmol) was added and the mixture stirred at 20 0C for 16 h. The solvent was evaporated and the residue partitioned between water (70 mL) and EtOAc (70 mL). The organic fraction was washed with water (30 mL), dried and the solvent evaporated. The crude solid was purified by column chromatography, eluting with a gradient (0-10%) of MeOH/EtOAc, to give benzamide 101 (328 mg, 56%) as a cream powder: mp (MeOH/EtOAc) 238- 241 0C; 1H NMR delta 12.74 (s, 1 H, CONH), 8.63 (dd, J= 4.5, 1.6 Hz, 2 H, H-2", H- 6"), 8.04 (br d, J= 8.0 Hz, 2 H, H-2, H-6), 8.02 (s, 1 H, H-5), 7.89 (dd, J= 4.6, 1.6 Hz, 2 H, H-3", H-5"), 7.35 (br d, J= 8.0 Hz, 2 H, H-3, H-5), 2.39 (s, 3 H, CH3); 13C NMR delta 165.2, 159.0, 150.1 (2), 146.5, 142.9, 140.9, 129.2 (2), 128.9, 128.1 (2), 119.2 (2), 112.5, 20.9; MS m/z 296.4 (MH+, 100%). Anal, calcd for Ci6Hi3N3OS: C, 65.06; H, 4.44; N, 14.23. Found: C, 64.96 H, 4.62; N, 14.24%.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 135

20
[ 267658-14-0 ]
[ 30235-28-0 ]
2-[3-(3-chloropropoxy)-phenyl]-N-(4-pyridin-4-yl-thiazol-2-yl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		2- [3- (3-CHLOROPROPOXY)-PHENYL]-N- (4-PYRIDIN-4-YL-THIAZOL-2-YL)-ACETAMIDE : A suspension of 1-methylsulfonylbenzentriazole (2.87 g, 0.0146 MOL), [3- (3-CHLORO-PROPOXY)- phenyl]-acetic acid (3.33 g, 0.0146 mol) and triethylamine (2.94 g, 0.0291 mol) was stirred at room temperature for 3 hours, then to the suspension was added 4-pyridin-4-yl-thiazol-2- ylamine, and the reaction mixture was refluxed for 20h, then cooled to room temperature. The precipitated solid was filtered, washed and dried to afford 2- [3- (3-CHLOROPROPOXY)- PHENYL]-N- (4-PYRIDIN-4-YL-THIAZOL-2-YL)-ACETAMIDE, (2. 5g, 64%).'H NMR (500 MHz, CD30D) 8 2.18 (m, 2H), 3.78 (s, 2H), 3.80 (t, 2H), 4.05 (t, 2H), 6.85 (dd, 1H), 6.9 (dd, 1H), 6.95 (d, 1H), 7.26 (dd, 1H), 7.85 (d, 2H), 8.02 (s, 1H), 8.63 (d, 2H).

Reference： [1]Patent: WO2004/41813,2004,A1 .Location in patent: Page 132-133

21
[ 30235-28-0 ]
[ 620-23-5 ]
C₁₆H₁₃N₃S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797

22
[ 30235-28-0 ]
[ 103-71-9 ]
[ 1328052-08-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	In N,N-dimethyl-formamide; at 150℃; for 0.166667h;	COMPl-Phenyl-3-(4-(pyridin-4-yl)thiazol-2-yl)urea. A mixture of 3a (0.081 g, 0.457 mmol), phenyl isocyanate (0.065 g, 0.559 mmol) in anhydrous DMF (0.5 ml), was stirred in a Biotage microwave at 150 C for 10 min After cooling to room temperature, the solvent was removed under reduced pressure and chromatography on silica gel performed using the FlashMaster 3 purification station afforded 6a as an off white solid (0.072 g, 0.243 mmol, 53%). 1H NMR (400 MHz, DMSO-d6) delta 10.77 (bs, 1H), 8.91 (bs, 1H), 8.60 (d, J= 6.0 Hz, 2H), 7.90 (s, 1H), 7.81 (d, J= 6.1 Hz, 2H), 7.47 (d, J= 8.3 Hz, 2H), 7.32 (t, J= 7.9 Hz, 2H), 7.04 (t, J= 7.4 Hz, 1H); HRMS (ESI +ve) m/z calculated for Ci5Hi3N4OS (M + H)+ 297.0804, found 297.0809.

Reference： [1]Patent: WO2011/130740,2011,A2 .Location in patent: Page/Page column 51
[2]MedChemComm,2012,vol. 3,p. 699 - 709

23
[ 30235-28-0 ]
[ 1195-45-5 ]
[ 1342277-11-5 ]

Yield	Reaction Conditions	Operation in experiment
28%	In N,N-dimethyl-formamide; at 150℃; for 0.333333h;Biotage microwave;	COMPOUND 6cl-(4-Fluorophenyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea. A mixture of 3a (0.095 g, 0.536 mmol), 4-fluorophenyl isocyanate (0.147 g, 1.073 mmol) in anhydrous DMF (0.6 ml), was stirred in a Biotage microwave at 150 C for 20 min After cooling to room temperature, the solvent was removed under reduced pressure and chromatography on silica gel performed using the FlashMaster 3 purification station afforded 6c as an off white solid (0.047 g, 0.149 mmol, 28%). 1H NMR (400 MHz, DMSO-d6) delta 10.82 (s, 1H), 8.96 (s, 1H), 8.59 (d, J= 6.0 Hz, 2H), 7.91 (s, 1H), 7.81 (d, J= 6.0 Hz, 2H), 7.50-7.46 (m, 2H), 7.16 (t, J = 8.8 Hz, 2H); HRMS (ESI +ve) m/z calculated for Ci5Hi2N4FOS (M + H)+ 315.0710, found 315.0713.

Reference： [1]Patent: WO2011/130740,2011,A2 .Location in patent: Page/Page column 52

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Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 30235-28-0 ] {[proInfo.proName]}

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[ 30235-28-0 ] Synthesis Path-Downstream 1~23

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