[ CAS No. 5198-87-8 ] {[proInfo.proName]}

Name: 5198-87-8|2-Chlorothiazole-4-carboxylic acid|97%
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Quality Control of [ 5198-87-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 5198-87-8 ]

CAS No. :	5198-87-8	MDL No. :	MFCD09870033
Formula :	C₄H₂ClNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UVYJJJQMZPCYKY-UHFFFAOYSA-N
M.W :	163.58	Pubchem ID :	21803026
Synonyms :

Safety of [ 5198-87-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5198-87-8 ]

* 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 [ 5198-87-8 ]
Downstream synthetic route of [ 5198-87-8 ]

[ 5198-87-8 ] Synthesis Path-Upstream 1~5

1
[ 41731-52-6 ]
[ 5198-87-8 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: With water; potassium hydroxide In ethanol at 0 - 20℃; Stage #2: With hydrogenchloride In water at 20℃; for 72 h;	14.0 g (73.1 mmol) of 2-chlorothiazole-4-carboxylic acid ethyl ester were slowly added to a solution of 1 1.0 g (0.17 mol, 85percent purity) of potassium hydroxide in ethanol/water (1 :3, 200 ml) at 0 ⁰C. The reaction mixture was stirred at room temperature for 16 h, diluted with water and washed twice with diethyl ether. The aqueous layer was acidified (pH = 5.5) with cone. HCI and stirred at room temperature for three days. The formed precipitate was collected by filtration and dried at 40 ⁰C under vaccum to yield 7.0 g (56percent, 95percent purity) of the title compound as a brown solid.

Reference： [1] Patent: WO2011/3796, 2011, A1, . Location in patent: Page/Page column 126; 127
[2] Helvetica Chimica Acta, 1944, vol. 27, p. 1432,1433
[3] Patent: US5498630, 1996, A,
[4] Patent: WO2007/146066, 2007, A2, . Location in patent: Page/Page column 152

2
[ 40283-41-8 ]
[ 5198-87-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: With hydrogenchloride; sodium nitrite In 1,4-dioxane; water at 0 - 5℃; for 2 h; Stage #2: With copper(l) chloride In 1,4-dioxane; water at 0 - 20℃; for 8 h;	Preparation of 2-chlorothiazole-4-carboxylic acid To a solution of 2.84 g (19.7 mmol) of 2-aminothiazole-4-carboxylic acid in 30 ml of 1,4-dioxane was added 50 ml of concentrated hydrochloric acid, followed by cooling to 0°C, and 10 ml of an aqueous solution of 2.04 g (29.6 mmol) of sodium nitrite was added charged dropwise thereto at 0°C to 5°C. The reaction liquid was stirred at 0°C for 2 hours, and then 2.93 g (29.6 mmol) of copper chloride was charged in separate portions thereto. The reaction liquid was returned to room temperature, followed by stirring for 8 hours. To the reaction liquid were added water and ethyl acetate, followed by extraction with ethyl acetate four times. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to prepare 1.77 g (yield 55percent) of a target compound. ¹H-NMR (DMSO-d₆, ppm) δ 8.41 (1H, s). The proton of the carboxylic acid was not detected.
55%	Stage #1: With hydrogenchloride; sodium nitrite In 1,4-dioxane at 0 - 5℃; for 2 h; Stage #2: With copper(l) chloride In 1,4-dioxane at 20℃; for 8 h;	To a solution of 2.84 g (19.7 mmol) of 2-aminothiazole-4-carboxylic acid in 30 ml of 1,4-dioxane was added 50 ml of concentrated hydrochloric acid, followed by cooling to 0°C, and 10 ml of an aqueous solution of 2.04 g (29.6 mmol) of sodium nitrite was charged dropwise thereto at 0°C to 5°C. The reaction liquid was stirred at 0°CFor 2 hours, and then 2.93 g (29.6 mmol) of copper chloride was charged in separate portions thereto. The reaction liquid was returned to room temperature, followed by stirring for 8 hours. To the reaction liquid were added water and ethyl acetate, followed by extraction with ethyl acetate four times. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to prepare 1.77 g (yield 55percent) of a target compound. ¹H-NMR (DMSO-d₆, ppm) δ 8.41 (1H, s). The proton presumed to be indicative of carboxylic acid was not detected.

Reference： [1] Patent: EP2319830, 2011, A1, . Location in patent: Page/Page column 343
[2] Patent: EP2325165, 2011, A1, . Location in patent: Page/Page column 460; 461

3
[ 850429-61-7 ]
[ 5198-87-8 ]

Reference： [1] Patent: WO2010/2209, 2010, A2, . Location in patent: Page/Page column 53-54

4
[ 43028-99-5 ]
[ 5198-87-8 ]

Reference： [1] Chimica Therapeutica, 1973, vol. 8, p. 199 - 201

5
[ 5198-87-8 ]
[ 75-65-0 ]
[ 1258934-67-6 ]

Reference： [1] Synthesis, 2010, # 18, p. 3152 - 3162

[ 5198-87-8 ] Synthesis Path-Downstream 1~22

1
[ 5198-87-8 ]
[ 43029-06-7 ]

Reference： [1]Helvetica Chimica Acta,1944,vol. 27,p. 1432,1433

2
[ 5198-87-8 ]
[ 70205-44-6 ]

Reference： [1]Helvetica Chimica Acta,1946,vol. 29,p. 1229

3
[ 41731-52-6 ]
[ 5198-87-8 ]

Yield	Reaction Conditions	Operation in experiment
56%		14.0 g (73.1 mmol) of 2-chlorothiazole-4-carboxylic acid ethyl ester were slowly added to a solution of 1 1.0 g (0.17 mol, 85% purity) of potassium hydroxide in ethanol/water (1 :3, 200 ml) at 0 0C. The reaction mixture was stirred at room temperature for 16 h, diluted with water and washed twice with diethyl ether. The aqueous layer was acidified (pH = 5.5) with cone. HCI and stirred at room temperature for three days. The formed precipitate was collected by filtration and dried at 40 0C under vaccum to yield 7.0 g (56%, 95% purity) of the title compound as a brown solid.
	With sodium hydroxide; In ethanol; water;	c) A mixture of NaOH (1.9 g, 47.5 mmol) and ethyl-2-chloro-4-thiazolecarboxylate (7.6 g, 40 mmol) in 100 mL absolute ethanol was stirred at RT for 4 h. After that, ethanol was removed in vacuo and the residue was dissolved in water. The aq layer was washed with ether and then acidified with conc HCl. The solid was filtered and air dried to give 4 g of 2-chloro-4-thiazolecarboxylic acid.
		The solid (7.64 g, 44.4 mmol) was added portionwise to a 60 C solution of Copper(II) chloride (7.46 g, 55.5 mmol) and t-butyl nitrite (8.2 mL, 66.6 mmol) in acetonitrile (175 mL) while maintaining the reaction temperature between 60 and 65 0C. After complete addition, the reaction mixture was heated to 80 C for 1 h. Upon cooling to rt, the reaction mixture was poured into a mixture Of CHaCl2 (150 mL), water (150 mL), and HCl (cone, 10 mL). The organics were separated and the aqueous layer was extracted with CH2Cl2 (2 x 100 mL). The combined organics were washed with brine (300 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting material was dissolved in EtOH (100 mL) and NaOH (2.13 g, 53.3 mmol) was added followed by water (50 mL). After stirring overnight at rt, the ethanol was removed under reduced pressure and the reaction mixture was diluted with water (50 mL). The mixture was washed with Et2O (50 mL, discarded) and brought to pH ~2 with cone. HCl. The resulting solid was collected by filtration, washed with water (3 x) and dried. This gave 4.73 g (63%) of the title compound as a yellow solid. LC-MS: RT = 4.35 min, [M+H]+ = 163.9.

Reference： [1]Patent: WO2011/3796,2011,A1 .Location in patent: Page/Page column 126; 127
[2]Helvetica Chimica Acta,1944,vol. 27,p. 1432,1433
[3]Patent: US5498630,1996,A
[4]Patent: WO2007/146066,2007,A2 .Location in patent: Page/Page column 152

4
[ 43028-99-5 ]
[ 5198-87-8 ]

Reference： [1]Chimica Therapeutica,1973,vol. 8,p. 199 - 201

6
[ 5198-87-8 ]
[ 960535-17-5 ]
[ 960535-84-6 ]

Yield	Reaction Conditions	Operation in experiment
79%		TBTU (592 mg, 1.85 mmol) was added to a solution of Intermediate C (361 mg, 1.23 mmol), 2-chlotauothiazole-4-carboxylic acid (221 mg, 1.35 mmol), and triethylamine (0.35 mL, 2.46 mmol) in DMF (4 ralphaL). After stirring overnight, IN NaOH (2 mL) was added, and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with EtOAc (30 mL) and washed with IN NaOH (2 x 20 mL) and brine (20 mL). The organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (50 to 70% EtOAc in hexanes gradient), yielding 429.2 mg (79%) of the desired product as a white solid. LC-MS: RT = 7.57 min, [M+H]+ = 438.9.

Reference： [1]Patent: WO2007/146066,2007,A2 .Location in patent: Page/Page column 152-153

7
[ 5198-87-8 ]
[ 918444-82-3 ]
[ 918444-88-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 18h;	EDC (3.37 g, 18.11 mmol) was added to a solution of 2-chlorothiazole-4- carboxylic acid (Intermediate 26; 2.82 g, 17.25 mmol), N2-(2-(tert- Butyldimethyl silyloxy) ethyl)-4,6-dimethoxypyrimidine-2,5-diamine(Intermediate 31; 5.7 g, 17.42 mmol), hydroxybenzotriazole (2.45 g, 18.11 mmol) and triethylamine (4.85 g, 34.5 mmol) in DCM (100 ml). The solution was stirred for a further 18h at ambient temperature and then the mixture was washed with aqueous citric acid solution (5 %; 50 ml) followed by washing with saturated aqueous sodium hydrogen carbonate solution (50 ml). The material was washed with brine, dried (MgSO4) and the solvent was removed EPO <DP n="61"/>in vacuo. The title compound was isolated by column chromatography (SiO2, elution 1 :7 ethyl acetate-petroleum ether) as a brown solid (4.5 g, 55 %). 1H NMR delta 7.99 ( 1 H, s), 7.91 (1 H, s), 5.15 (1 H1 br t), 3.80 (6 H, s), 3.69 (2 H, t), 3.45 (2 H, q), 0.84 (9 H, s) and 0.0 (6 H, s); m/z 474.12 (MH+)

Reference： [1]Patent: WO2007/582,2007,A1 .Location in patent: Page/Page column 59-60

8
N-[4-(aminomethyl)-2,6-difluorophenyl]methanesulfonamide hydrochloride [ No CAS ]
[ 5198-87-8 ]
[ 1202643-24-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; at 20℃;	Methyl-2-chlorothiazole-4-carboxylate (2g, 11.26mmol) was dissolved in ethanol solution, to which was added excess c-HCl , and the resulting mixture was refluxed for 30 minutes. The reaction mixture was concentrated, and the crude acid (151mg, 0.92mmol) was dissolved in THF. To the resulting solution was added N-(4-aminomethyl-2,beta~difluoro-phenyl)-methanesulfonamide, HCl salt (250mg, 0.92mmol) followed by DMTMM. The reaction mixture was stirred overnight at room temperature, and then diluted with EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (Hex/EtOAc=l:l) to give the title product (263mg, 0.69mmol).<484> 1H NMR(300MHz, DMS0-d6): delta9.43(s, IH), 9.20(s, IH), 8.24(s, IH),7.15(s, IH), 7.09(s, IH), 4.4Kd1 2H, J=6.0Hz), 3.03(s, 3H).

Reference： [1]Patent: WO2010/2209,2010,A2 .Location in patent: Page/Page column 53-54

9
[ 850429-61-7 ]
[ 5198-87-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; In ethanol; for 0.5h;Reflux;	Methyl-2-chlorothiazole-4-carboxylate (2g, 11.26mmol) was dissolved in ethanol solution, to which was added excess c-HCl , and the resulting mixture was refluxed for 30 minutes. The reaction mixture was concentrated, and the crude acid (151mg, 0.92mmol) was dissolved in THF.

Reference： [1]Patent: WO2010/2209,2010,A2 .Location in patent: Page/Page column 53-54

10
[ 5198-87-8 ]
[ 75-65-0 ]
[ 1258934-67-6 ]

Reference： [1]Synthesis,2010,p. 3152 - 3162

11
[ 5198-87-8 ]
[ 16401-70-0 ]
[ 1261079-97-3 ]

Yield	Reaction Conditions	Operation in experiment
61%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	200 mg (1.2 mmol) of 2-chlorothiazole-4-carboxylic acid and 96.1 mg (0.9 mmol) of pyridazin-4-yl-amine were dissolved in 6 ml dimethyl formamide. 0.15 ml. (1.1 mmol) of triethyl amine followed by 382 mg (0.73 mmol) of 1 H-Benzotriazol-1- yloxytri-pyrrolidinophosphonium hexafluorophosphate (PyBOP) were added and the reaction mixture was stirred at room temperature for 16 h. Brine was added and the reaction mixture was extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The obtained residue was purified by flash column chromatography (silica, gradient elution cyclohexane? ethyl ace- tate? methanol) to give 200 mg (61 %, 95% purity) of the title compound.

Reference： [1]Patent: WO2011/3796,2011,A1 .Location in patent: Page/Page column 127

12
[ 40283-41-8 ]
[ 5198-87-8 ]

Yield	Reaction Conditions	Operation in experiment
55%		Preparation of 2-chlorothiazole-4-carboxylic acid To a solution of 2.84 g (19.7 mmol) of <strong>[40283-41-8]2-aminothiazole-4-carboxylic acid</strong> in 30 ml of 1,4-dioxane was added 50 ml of concentrated hydrochloric acid, followed by cooling to 0C, and 10 ml of an aqueous solution of 2.04 g (29.6 mmol) of sodium nitrite was added charged dropwise thereto at 0C to 5C. The reaction liquid was stirred at 0C for 2 hours, and then 2.93 g (29.6 mmol) of copper chloride was charged in separate portions thereto. The reaction liquid was returned to room temperature, followed by stirring for 8 hours. To the reaction liquid were added water and ethyl acetate, followed by extraction with ethyl acetate four times. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to prepare 1.77 g (yield 55%) of a target compound. 1H-NMR (DMSO-d6, ppm) delta 8.41 (1H, s). The proton of the carboxylic acid was not detected.
55%		To a solution of 2.84 g (19.7 mmol) of <strong>[40283-41-8]2-aminothiazole-4-carboxylic acid</strong> in 30 ml of 1,4-dioxane was added 50 ml of concentrated hydrochloric acid, followed by cooling to 0C, and 10 ml of an aqueous solution of 2.04 g (29.6 mmol) of sodium nitrite was charged dropwise thereto at 0C to 5C. The reaction liquid was stirred at 0CFor 2 hours, and then 2.93 g (29.6 mmol) of copper chloride was charged in separate portions thereto. The reaction liquid was returned to room temperature, followed by stirring for 8 hours. To the reaction liquid were added water and ethyl acetate, followed by extraction with ethyl acetate four times. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to prepare 1.77 g (yield 55%) of a target compound. 1H-NMR (DMSO-d6, ppm) delta 8.41 (1H, s). The proton presumed to be indicative of carboxylic acid was not detected.

Reference： [1]Patent: EP2319830,2011,A1 .Location in patent: Page/Page column 343
[2]Patent: EP2325165,2011,A1 .Location in patent: Page/Page column 460; 461

13
[ 5198-87-8 ]
[ 1361189-49-2 ]
5-(4-{1-[5-(2-chloro-thiazol-4-yl)-[1,2,4]oxadiazol-3-yl]-cyclobutyl}-phenyl)pyrimidin-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 : Synthesis of 5-(4-f l-r5-(2-Chloro-thiazol-4-yl)-ri,2,41oxadiazol-3-yl1- cyclobutyl\|-phenyl)-pyrimidin-2-ylamine (R83)To a suspension of R82 (173 mg, 1.06 mmol) in THF (5 ml) is added CDI (72 mg, 1.06 mmol) at room temperature. The mixture is stirred at 50C for 30 minutes. After this time 1-2.5 (200 mg, 0.71 mmol) is added and the resulting mixture is heated 80C for 3 hours. The mixture is cooled to ambient temperature and treated with AcOH (0.5 ml). After warming to 80C the reaction is stirred over night. Upon cooling to room temperature the reaction is poured into water and EtOAc. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organics are dried (MgS04), filtered and concentrated to give the crude which is purified via column chromatography (25g silica gel, 0-8% MeOH/DCM). Product-containing fractions are concentrated to give R83 (120 mg) m/z 411.1

Reference： [1]Patent: WO2012/27322,2012,A1 .Location in patent: Page/Page column 147

14
[ 5198-87-8 ]
[ 1555700-69-0 ]
[ 1555692-60-8 ]

Yield	Reaction Conditions	Operation in experiment
22%		[00222] Example 6: A solution of <strong>[5198-87-8]2-chlorothiazole-4-carboxylic acid</strong> (148 mg, 0.906 mmol), diphenyl phosphorazidate (0.20 mL, 1.0 mmol) in toluene (3 mL) was stirred at room temperature for 5 min before slowly warming up to 100 C. When the reaction reached 40 C, Example 6A (23.7 mg) in toluene (3 mL) was added. The reaction mixture was heated at 100 C for 90 min before gradually cooling down to room temperature. The reaction was then concentrated and purified by Prep HPLC (TFA) to give Example 6 (48 mg, 22% yield) as a brown solid. LCMS (ESI) m/z 493, 495 (M+H, M+2+H)+, RT = 2.05 min (Method J). lH NMR (300 MHz, DMSO-d6) delta ppm 1.38 (s, 3H), 1.48 (s, 3H), 3.03 (d, J = 10.25 Hz, 1H), 3.85 (d, J = 9.88 Hz, 1H), 6.54 (d, J = 8.42 Hz, 1H), 6.79-6.96 (m, 3H), 7.00-7.17 (m, 1H), 7.28 (s, 1H), 8.06 (d, J = 7.68 Hz, 1H), 8.52 (s, 1H), 9.18 (s, 1H), 10.20 (s, 1H).

Reference： [1]Patent: WO2014/22343,2014,A1 .Location in patent: Paragraph 00222

15
[ 5198-87-8 ]
[ 1617505-01-7 ]
[ 1617505-27-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 6150 - 6164

16
[ 5198-87-8 ]
2-((4-chloro-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)benzo[d]thiazol-6-yl)oxy)ethanol [ No CAS ]
2-((4-chloro-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)benzo[d]thiazol-6-yl)oxy)ethyl (2-chlorothiazol-4-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With diphenylphosphoranyl azide; triethylamine; In toluene; at 110℃; for 3h;	To a suspension of Example 318 (12 mg, 0.029 mmol) and 2-chlorothiazole-4- carboxylic acid (9.35 mg, 0.057 mmol) in Toluene (1 mL) was added triethylamine (7.97pi, 0.057 mmol) followed by diphenylphosphoryl azide (15.73 mg, 0.057 mmol). The reaction vessel was then sealed and heated to 110 C for 3 hours. The resulting mixture was cooled to room temperature, concentrated and purified by preparative HPLC (Method D, 60-100% over 20 mm, hold at 100% for 10 mm) to afford Example 383 in 20% yield. LC-MS. Method H, RT = 1.35 mm, MS (ESI) m/z: 580.1 (M+H). ?H NIVIR(500IVIHz, DMSO-d6) 9.71 (br. s., 1H), 8.73 (s, 1H), 8.58 (d, J=1.4 Hz, 1H), 8.21 (br.s., 1H), 8.07 (d, J=7.4 Hz, 1H), 7.85 (s, 1H), 7.77 (br. s., 1H), 6.77 (d, J=8.3 Hz, 1H),4.92 (td, J=6.2, 3.3 Hz, 1H), 4.46-4.27 (m, 2H), 4.10 (s, 3H), 3.78 (s, 3H), 2.66 (s, 3H),1.43 (d,J=6.3 Hz, 3H).

Reference： [1]Patent: WO2018/13774,2018,A1 .Location in patent: Page/Page column 776

17
[ 5198-87-8 ]
[ 24424-99-5 ]
tert-butyl 2-chlorothiazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.4%	With dmap; In tetrahydrofuran; at 60℃; for 1h;	To a solution of <strong>[5198-87-8]2-chlorothiazole-5-carboxylic acid</strong> (XXXV) (1.0 g, 6.11 mmol), di-tert-butyl dicarbonate (3.07 g, 14.06 mmol) in THF (19.8 mL) was added DMAP (0.15 g, 1.22 mmol). The reaction was heated at 60 C. for 1 h. The solvent was removed under vacuum and the residue was purified by silica gel (40 g) (0?50% EtOAc/hexanes) to produce tert-butyl 2-chlorothiazole-4-carboxylate (XXXVI) as a clear liquid (1.05 g, 4.79 mmol, 78.4% yield). ESIMS found for C8H10C1NO2S m/z 220.0 (M+H).

Reference： [1]Patent: US2019/125741,2019,A1 .Location in patent: Paragraph 0624-0625

18
[ 163271-08-7 ]
[ 5198-87-8 ]
tert-butyl (1-(2-chlorothiazole-4-carbonyl)-4-methylpiperidin-4-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 5h;	Step 1 : A round bottomed flask was charged with 2-chlorothiazole-4-carboxylic acid (75 mg, 0.4584 mmol), N-ethyl-N-isopropylpropan-2-amine (118 mg, 0.9168 mmol), and a stirbar. Dimethylformamide (2 mL) was added, followed by l- (1115) ((dimethylamino)(dimethyliminio)methyl)-3-oxo-l,3-dihydro-[l,2,3]triazolo[4,5-b]pyridin-3- ium-2-ide hexafluorophosphate(V) (209 mg, 0.5500 mmol) and tert-butyl (4-methylpiperidin- 4-yl)carbamate (117 mg, 0.5500 mmol). The solution was stirred at 20 C for 5 h. DMF was removed in a Genevac. The resulting crude material was purified by silica gel (1116) chromatography (10 g column; eluting with heptanes/ ethyl acetate). Concentration in vacuo resulted in tert-butyl (l-(2-chlorothiazole-4-carbonyl)-4-methylpiperidin-4-yl)carbamate (118 mg, 70% ) as a white amorphous solid. LCMS M/Z: 382 (MTNa).

Reference： [1]Patent: WO2019/165073,2019,A1 .Location in patent: Paragraph 0347

19
[ 5198-87-8 ]
C₁₅H₁₅N₇*2C₂HF₃O₂ [ No CAS ]
N-{2-[4-amino-7-(1H-pyrazol-3-yl)-2H-pyrazolo[4,3-c]quinolin-2-yl]ethyl}-2-chloro-1,3-thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		To a rt solution of <strong>[5198-87-8]2-chlorothiazole-4-carboxylic acid</strong> (9.39 mg, 0.057 mmol) in DMF (130 pl) was added N,N-diisopropylethylamine (18.17 m, 0.104 mmol), followed by HATU (19.84 mg, 0.052 mmol). This mixture was stirred at rt for 5 min, then it was added, dropwise, to a solution of 2-(2-aminoethyl)-7-(lH-pyrazol-3-yl)-2H-pyrazolo[4,3- c]quinolin-4-amine, 2 TFA (27.2 mg, 0.052 mmol) and N,N-diisopropylethylamine (27.3 m, 0.157 mmol) in DMF (130 m). The reaction was stirred at rt for 30 min. The reaction was diluted with H2O (0.1 mL) and DMF (to a total volume of 2 mL), filtered (syringe filter), and purified via preparative LC/MS with the following conditions: Column: XBridge C18, 200 mm x 19 mm, 5-pm particles; Mobile Phase A: 5:95 acetonitrile: water with l0-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with l0-mM ammonium acetate; Gradient: a 0-minute hold at 7% B, 7-47% B over 20 minutes, then a 4-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS and UV signals. Fractions containing the desired product were combined and dried via centrifugal evaporation to provide N-(2-(4-amino-7-(lH- pyrazol-3-yl)-2H-pyrazolo[4,3-c]quinolin-2-yl)ethyl)-2-chlorothiazole-4-carboxamide (14.7 mg, 64%). NMR (500 MHz, DMSO-de) d 8.83 (br t, J= 5.5 Hz, 1H), 8.44 (s, 1H), 8.23 (s, 1H), 8.09 (d, =8.3 Hz, 1H), 7.87 (s, 1H), 7.71 (br s, 1H), 7.63 (br d, =7.7 Hz, 1H), 6.99 - 6.88 (m, 2H), 6.76 (d, .7=1.9 Hz, 1H), 4.60 (br t, =5.6 Hz, 2H), 3.82 - 3.75 (m, 2H). Analytical LC/MS conditions: Column: Waters XBridge C18, 2.1 mm x 50 mm, 1.7 mhi particles; Mobile Phase A: 5:95 acetonitrile:water with 0.1 % trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile:water with 0.1 % trifluoroacetic acid; Temperature: 50 C; Gradient: 0 %B to 100 %B over 3 min, then a 0.50 min hold at 100 %B; Flow: 1 mL/min; Detection: MS and UV (220 nm). m/z 439.0 [M+H]+; RT: 1.16 mm.

Reference： [1]Patent: WO2019/209896,2019,A1 .Location in patent: Paragraph 202

20
[ 123-00-2 ]
[ 5198-87-8 ]
N-(3-morpholinopropyl) 2-chlorothiazole-4-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019

21
[ 5198-87-8 ]
[ 2906-12-9 ]
2-chloro-N-(3-isopropoxypropyl)thiazole-4-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019

22
[ 5198-87-8 ]
[ 6291-85-6 ]
2-chloro-N-(3-ethoxypropyl)thiazole-4-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019

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[ CAS No. 5198-87-8 ] {[proInfo.proName]}

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[ 5198-87-8 ] Synthesis Path-Upstream 1~5

[ 5198-87-8 ] Synthesis Path-Downstream 1~22

Related Functional Groups of [ 5198-87-8 ]

Chlorides

Carboxylic Acids

Related Parent Nucleus of [ 5198-87-8 ]

Thiazoles

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