[ CAS No. 66909-30-6 ]

Name: 66909-30-6|2-Chloro-5-methylnicotinic acid|97%
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Quality Control of [ 66909-30-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 66909-30-6 ]

CAS No. :	66909-30-6	MDL No. :	MFCD07375371
Formula :	C₇H₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HGTOSTXLRLIKCJ-UHFFFAOYSA-N
M.W :	171.58 g/mol	Pubchem ID :	12387730
Synonyms :

Calculated chemistry of [ 66909-30-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.17
TPSA :	50.19 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) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.23
Log Po/w (XLOGP3) :	1.7
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	-0.18
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	1.26

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	0.836 mg/ml ; 0.00487 mol/l
Class :	Soluble
Log S (Ali) :	-2.37
Solubility :	0.733 mg/ml ; 0.00427 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.4
Solubility :	0.688 mg/ml ; 0.00401 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 66909-30-6 ]

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 [ 66909-30-6 ]

* 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 [ 66909-30-6 ]
Downstream synthetic route of [ 66909-30-6 ]

[ 66909-30-6 ] Synthesis Path-Upstream 1~7

1
[ 67-56-1 ]
[ 66909-30-6 ]
[ 65169-43-9 ]

Reference： [1] Patent: WO2007/41052, 2007, A2, . Location in patent: Page/Page column 78-79

2
[ 65169-43-9 ]
[ 66909-30-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	at 20℃; for 2 h;	INTERMEDIATE 322-Chloro-5-methylnicotinic acid; Intermediate 31 (0.38g, 1.81mmol) was dissolved in MeOH (2ml) and 2N NaOH solution was added (1.81ml, 3.62mmol) and the mixture stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness and the residue redissolved in EtOAc/ <n="29"/>water. The organic layer was separated, dried over magnesium sulphate and concentrated in vacuum to yield the desired product as a white solid. Yield=94percent LRMS: m/z 172 (M+1 )⁺ Retention time: 3.25min ¹H NMR (200 MHz, DMSO-D₆) δ ppm: 2.2 (s, 3 H); 7.6 (d, 7=2.53 Hz, 1 H); 8.0 (d, J=2.53 Hz, 1 H)

Reference： [1] Patent: WO2008/77639, 2008, A1, . Location in patent: Page/Page column 26-27

3
[ 124-38-9 ]
[ 66909-30-6 ]

Reference： [1] Patent: US2005/20611, 2005, A1, . Location in patent: Page/Page column 24
[2] Patent: WO2007/41052, 2007, A2, . Location in patent: Page/Page column 78-79

4
[ 124-38-9 ]
[ 66909-30-6 ]

Reference： [1] Patent: WO2007/108750, 2007, A1, . Location in patent: Page/Page column 78-79

5
[ 18368-64-4 ]
[ 124-38-9 ]
[ 66909-30-6 ]

Reference： [1] Patent: WO2005/9965, 2005, A1, . Location in patent: Page/Page column 42

6
[ 18368-64-4 ]
[ 66909-30-6 ]

Reference： [1] Patent: WO2007/108750, 2007, A1,

7
[ 64-17-5 ]
[ 66909-30-6 ]
[ 894074-85-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5 h; Stage #2: for 2 h;	Ethyl 2-chloro-5-methylnicotinate. To a solution of 2-chloro-5-methylnicotinic acid (3.90 g, 22.7 mmol) in DCM (100 ml_) was added oxalyl chloride (9.95 ml_, 1 14 mmol) followed by 1 drop of DMF. The resulting mixture was stirred at RT for 30 min and evaporated in vacuo. The residue thus obtained was taken up into EtOH (66 ml_), stirred for a further 2 hr and then evaporated in vacuo. The crude product obtained was purified by flash column chromatography (S1O2, 120 g, 0-50percent DCM in isohexane, gradient elution) to afford the title compound as a colourless oil (3.71 g, 82percent yield); ¹ H NMR δ: 1.32 (3H, t), 2.34 (3H, s), 4.34 (2H, q), 8.06-8.07 (1 H, m), 8.41-8.43 (1 H, m). [See also: Yamamoto S. et al., Bioorg. Med. Chem. 2012, 20, 422-434.]
82%	Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5 h; Stage #2: for 2 h;	To a solution of 2-chloro-5-methylnicotinic acid (3.90 g, 22.7 mmol) in DCM (100 mL) was added oxalyl chloride (9.95 mL, 114 mmol) followed by 1 drop of DMF. The resulting mixture was stirred at RT for 30 min and evaporated in vacuo. The residue thus obtained was taken up into EtOH (66 mL), stirred for a further 2 hr and then evaporated in vacuo. The crude product obtained was purified by flash column chromatography (S1O2, 120 g, 0-50percent DCM in isohexane, gradient elution) to afford the title compound as a colourless oil (3.71 g, 82percent yield); ¹ H NMR δ: 1.32 (3H, t), 2.34 (3H, s), 4.34 (2H, q), 8.06-8.07 (1 H, m), 8.41 -8.43 (1 H, m). [See also: Yamamoto S. et al., Bioorg. Med. Chem. 2012, 20, 422-434.]

Reference： [1] Patent: WO2016/55791, 2016, A1, . Location in patent: Page/Page column 12
[2] Patent: WO2017/175000, 2017, A1, . Location in patent: Page/Page column 28

[ 66909-30-6 ] Synthesis Path-Downstream 1~32

Yield	Reaction Conditions	Operation in experiment
		REFERENCE EXAMPLE 7 The preparation Of 2-chloro-5-methylnicotinic acid An aqueous solution of sodium hydroxide (9.2 g) was added to an ice-cooled, stirred solution of methyl 2-chloro-5-methylnicotinoate (35.28 g) in methanol at such a rate so that the temperature of the reaction mixture did not exceed 30 C. The mixture was then stirred at room temperature for 1.5 hours. Solvent was evaporated. The residue was diluted with water and acidified to pH 2 with concentrated hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to yield the title compound as a pale yellow solid, 31.92 g, m.p. 180-180.5 C.
		Reference Example 3 The preparation of 2-chloro-5-methylnicotinic acid An aqueous solution of sodium hydroxide (9.2 g) was added to an ice-cooled, stirred solution of methyl 2-chloro-5-methylnicotinoate (35.28 g) in methanol at such a rate so that the temperature of the reaction mixture did not exceed 30 C. The mixture was then stirred at room temperature for 1.5 hours. Solvent was evaporated. The residue was diluted with water and acidified to pH 2 with concentrated hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to yield the title compound as a pale yellow solid, 31.92 g, m.p. 180-180.5 C.

2
C₆H₅ClLiN [ No CAS ]
[ 124-38-9 ]
[ 66909-30-6 ]

Yield	Reaction Conditions	Operation in experiment
		1.6 M solution of butyllithium in hexanes (6.03 g, 58.8 ml, 94.1 mmol) was added to THF (200 ml) and the mixture was cooled to -78C. The mixture was treated dropwise with 2,2,6,6-tetramethylpiperidine (13.29 g, 17.6 ml, 94.1 mmol) and stirred at -78 0C for 30 min. The solution was then treated dropwise with 2-chloro-5-methyl-pyridine (12 g, 94.1 mmol) in THF (20 ml) and the reaction mixture was stirred at -780C for a further 2.5h. The mixture was then poured onto dry ice and allowed to warm to room temperature overnight. The mixture was partitoned between diethyl ether and water, and the aqueous layer was then acidified to pH 2 with 2M HCl and the solvent concentrated to about 100 ml. The suspension was stored in the fridge for 48 hours, before being filtered and dried to afford the sub-title compound (5.6 g, 35%). <n="80"/>1HNMR (400 MHz, DMSO-J6) delta 13.70 (broad s, IH), 8.38 (d, IH), 8.05 (d5 IH), 2.34 (s, 3H)

Reference： [1]Patent: WO2007/108750,2007,A1 .Location in patent: Page/Page column 78-79

3
[ 21926-00-1 ]
[ 66909-30-6 ]
[ 950901-86-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate;copper; copper(I) bromide; In N,N-dimethyl-formamide; at 150℃; for 1.5h;	2-Chloro-5-methyl-nicotinic acid (2.5 g, 14.6 mmol) and K2CO3 (2.4 g, 17.5 mmol) were added to dry DMF (20 ml). Copper (55.6 mg, 0.87 mmol), copper(I)bromide (104.5 mg, 0.73 mmol) and tetrahydro-thiopyran-4-ylamine (2.9 g, 24.8 mmol) were added and the reaction mixture was stirred at 1500C for 1.5h. The mixture was cooled to room temperature and ethyl acetate was added. The reaction mixture was washed with 0.5M aq. citric acid. The aqueous layer was adjusted to pH 5 with aqueous ammonia and extracted with ethyl acetate (x3). The combined organic extracts were dried (anhydrous Na2SO4), filtered and evaporated. Water was added to the residue and the resulting solid was collected by filtration and dried in vacuo to afford the sub-title compound. (1.48 g, 40%). 1H NMR (400 MHz, DMSO-J6) delta 8.10 (dd, IH), 7.94 - 7.88 (m, IH), 4.06 - 3.98 (m, IH), 2.75 - 2.61 (m, 4H), 2.21 - 2.18 (m, 2H), 2.14 (s, 3H), 1.57 (dtd, 2H)

Reference： [1]Patent: WO2007/108750,2007,A1 .Location in patent: Page/Page column 79

4
[ 124-38-9 ]
[ 66909-30-6 ]

Yield	Reaction Conditions	Operation in experiment
		2,2,6,6-Tetramethylpiperidine (4.4 ml, 26 mmol) was added to a cooled (-78 C.) solution of n-butyl lithium (9.4 ml, 2.5M in hexane, 23.5 mmol) in tetrahydrofuran (50 ml), and the solution stirred for 30 minutes. 2-Chloro-5-methylpyridine (3 g, 23.5 mmol) was then added, and the reaction stirred at -78 C. for 2.5 hours. The solution was poured onto solid carbon dioxide, and warmed to room temperature using a water bath. The solution was extracted with water, the aqueous acidified using 2N HCl, and extracted with ether. These organic extracts were washed with water and brine, then dried (MgSO4) and evaporated under reduced pressure to afford the title compound as a yellow solid, 1.65 g. 1H-NMR (CDCl3, 400 MHz) delta: 2.41 (s, 3H), 8.16 (s, 1H), 8.41 (s, 1H) LRMS: m/z APCI+ 172 [MH]+
		Intermediate R-I was prepared using a synthetic procedure analogues to the procedure in Scheme Q using the difluorophenyl analog of P-4.; Step A:; 2,2,6,6-Tetramethylpiperidine (88 mL, 0.52 mol) was added into a cooled (-780C) solution of n- BuLi (188 mL, 2.5 M in hexane, 0.47 mol) in anhydrous THF (1 L), and the solution was stirred for 30 minutes. Compound S-I (60 g, 0.47 mol) was added in portions and the mixture stirred at -781C for 2.5 hours. The reaction solution was poured onto dry ice and was allowed to warm to r.t. The reaction mixture was extracted with water and the aqueous layer was acidified to pH~3-4 with 2 N HCl. The product was extracted with ether (3 x IL). The combined organic phases were washed with water (250 mL) and brine (250 mL), then dried over MgSO4, filtered and concentrated under reduced pressure to afford compound S-2 (1HNMR(CD3OD), delta: 8.31 ppm (IH); 8.10 ppm (IH); 3.71 ppm (IH); 2.35 ppm (3H)).

Reference： [1]Patent: US2005/20611,2005,A1 .Location in patent: Page/Page column 24
[2]Patent: WO2007/41052,2007,A2 .Location in patent: Page/Page column 78-79

5
tert-butyl cis-4-aminocyclohexylcarbamate [ No CAS ]
[ 66909-30-6 ]
cis-{4-[(2-chloro-5-methyl-pyridine-3-carbonyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-carbonyldiimidazole; In DMF (N,N-dimethyl-formamide); at 20℃; for 73h;	Preparation 45 SYN-F4-R (2-CHLORO-5-METHYL-PYRIDINE-3-CARBONYL)-AMINOL-CVCLOHEXYL}-CARBAMIC acid TERT-BUTYL ESTER The carboxylic acid of preparation 2 (1.50g, 8. 74MMOL) was dissolved in N, N- DIMETHYLFORMAMIDE (15mL) and the solution treated with N, N -CARBONYLDIIMIDAZOLE (1.42g, 8. 74MMOL) and stirred at room temperature for 1 hour. The reaction mixture was treated with the amine of preparation 3 (2. 1 OU, 9. 63MMOL) and stirred at room temperature for 72 hours. The reaction mixture was concentrated in vacuo and the residue taken up in 10% citric acid solution and ether. The organic layer was separated and washed with 10% citric acid solution, water, saturated sodium hydrogencarbonate solution and brine. The organic layer was then dried over magnesium sulphate and concentrated in vacuo to yield the title product as a white foam, 3.61 g. HNMR (CDCI3, 400MHZ) : 1.44 (s, 9H), 1.61-1. 93 (m, 8H), 2.36 (s, 3H), 3.62 (m, 1 H), 4. 18 (m, 1 H), 4.54 (m, 1 H), 6.57 (m, 1 H), 7.96 (m, 1 H), 8.27 (m, 1 H). MS ES+ m/z 288 [MH] +

Reference： [1]Patent: WO2005/9965,2005,A1 .Location in patent: Page/Page column 64-65

6
[ 67-56-1 ]
[ 66909-30-6 ]
[ 65169-43-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step B:; To the cooled (0C) solution of compound S-2 (4.3 g, 25 mmol) in MeOH (75 mL) was added dropwise concentrated sulfuric acid (5 mL). The resulting reaction mixture was heated to reflux for 3 hours. After cooling to room temperature, the mixture was concentrated and the resulting residue was partitioned between CH2CI2 (100 mL) and water (50 mL). The aqueous phase was neutralized to pH ~7 with NaHCO3. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3 x 40 mL). The combined organic phases were washed with water, brine, dried over MgSO4, filtered and concentrated to afford the compound S-3 (m/z (ES) (M+H)+=186), which was used in the next step without further purification.

Reference： [1]Patent: WO2007/41052,2007,A2 .Location in patent: Page/Page column 78-79

7
[ 65169-43-9 ]
[ 66909-30-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With methanol; sodium hydroxide; water; at 20.0℃; for 2.0h;	INTERMEDIATE 322-Chloro-5-methylnicotinic acid; Intermediate 31 (0.38g, 1.81mmol) was dissolved in MeOH (2ml) and 2N NaOH solution was added (1.81ml, 3.62mmol) and the mixture stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness and the residue redissolved in EtOAc/ <n="29"/>water. The organic layer was separated, dried over magnesium sulphate and concentrated in vacuum to yield the desired product as a white solid. Yield=94% LRMS: m/z 172 (M+1 )+ Retention time: 3.25min 1H NMR (200 MHz, DMSO-D6) delta ppm: 2.2 (s, 3 H); 7.6 (d, »7=2.53 Hz, 1 H); 8.0 (d, J=2.53 Hz, 1 H)

Reference： [1]Patent: WO2008/77639,2008,A1 .Location in patent: Page/Page column 26-27

8
[ 18368-64-4 ]
[ 124-38-9 ]
[ 66909-30-6 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 2 2-CHLORO-5-METHYL-NICOTINIC acid A 2.5M solution of butyllithium in hexane (9.4mL, 23. 5mmol) was added to tetrahydrofuran (50mL) and the mixture cooled TO-78C. The mixture was treated with 2,2, 6, 6-TETRAMETHYLPIPERIDINE (4.4mL, 26. OMMOL) and stirred AT-78C for 30 minutes. The reaction mixture was then treated with 2-chloro-5-methylpyridine (3. 00g, 23. 5MMOL) and stirred AT-78C for a further 2.5 hours. The reaction mixture was poured into a beaker of dry ice and warmed to room temperature on a water bath, then extracted into water. The mixture was acidified with 2M hydrochloric acid, extracted into ether and washed with water (x 2) and brine. The solution was dried over magnesium sulphate to yield the title product as a yellow solid, 1.65g. HNMR (CDC13, 400MHZ) : 2.35 (s, 3H), 8.13 (m, 1H), 8. 42 (m, 1H). MS ES+ M/Z 172 [MH] +

Reference： [1]Patent: WO2005/9965,2005,A1 .Location in patent: Page/Page column 42

9
[ 580-17-6 ]
[ 66909-30-6 ]
2-chloro-6-methyl-N-(quinolin-3-yl)nicotinamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6653 - 6656

10
[ 66909-30-6 ]
(2-chloro-5-methylpyridin-3-yl)methanol [ No CAS ]

Reference： [1]Patent: WO2015/91411,2015,A1

11
[ 66909-30-6 ]
tert-butyl 4-(3-(hydroxymethyl)-5-methylpyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/91411,2015,A1

12
[ 541-41-3 ]
[ 66909-30-6 ]
C₁₀H₁₀ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 5℃; for 1h;	To a solution of <strong>[66909-30-6]2-chloro-5-methylnicotinic acid</strong> (1.5 g, 8.6 mmol) and triethylamine (0.92 g, 1.3 ml, 9.1 mmol) in tetrahydrofuran (24 ml) was added ethyl chloroformate (0.98 g, 0.87 ml, 9.1 mmol) at 0-5 C. The ice bath was removed after 5 minutes and stirring was continued for 1 h. The solids were removed by filtration and washed with tetrahydrofuran. The filtrate was concentrated in vacuo to give the crude mixed anhydride. To a solution of lithium aluminum hydride (0.34 g, 9.1 mmol) in tetrahydrofuran (18 ml) was added the mixed anhydride from above as a solution in tetrahydrofuran (9 ml) at -78 C in approximately 20 minutes. Stirring was continued for 2 h. The reaction mixture was quenched by addition of water (0.34 ml), 2 M aqueous sodium hydroxide solution (0.34 ml) and again water (1.02 ml) at -70 C. The dry ice / acetone bath was removed and stirring was continued for 1 h. The precipitate was removed by filtration and washed with tetrahydrofuran. The filtrate was concentrated in vacuo to give the title compound (1.1 g, 82%) as white solid, which was used in the next step without further purifications. MS m/e: 158 [(M+H)+].

Reference： [1]Patent: WO2015/91411,2015,A1 .Location in patent: Page/Page column 54

13
[ 66909-30-6 ]
ethyl 6-(4-(5-methyl-2-(7-oxa-2-azaspiro[3.5] nonan-2-yl)nicotinamido)benzoyl)-5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/55791,2016,A1

14
[ 66909-30-6 ]
6-(4-(5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)nicotinamido)benzoyl)-5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/55791,2016,A1

15
[ 66909-30-6 ]
6-(4-(2-chloro-5-methylnicotinamido)benzoyl)-N-(2-fluoro-6-methylphenyl)-5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/55791,2016,A1

16
[ 66909-30-6 ]
2-chloro-5-methylnicotinoylchloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 18 - 25℃; for 1h;	6-(4-(2-Chloro-5-methylnicotinamido)benzoyl)-W-(2-fluoro-6-methylphenyl)-5,6-di hydro-4H-benzo[i)]thieno[2,3-c ]azepine-2-carboxamide; Intermediate (Ilia). Oxalyl chloride (133 mL, 1.58 mol) was added to a suspension of 2-chloro-5-methyl nicotinic acid (225.4 g, 1.313 mol) in DCM (2254 mL) at 18-25C followed by DMF (0.8 mL, 0.010 mol) (results in mild exotherm and gas evolution) and the reaction stirred at 20-25C for 1 hr. HPLC analysis of an aliquot (quenched into methanol) indicated <1 % of 2-chloro-5- methylnicotinic acid was remaining. The solvent was removed in vacuo and the oily residue was azeotroped with DCM (500 mL) to remove residual oxalyl chloride. The resulting oil was taken up into DCM (413 mL) and was added dropwise over 10 min to a suspension of 6-(4-aminobenzoyl)-/V-(2-fluoro-6-methylphenyl)-5,6-dihydro-4/-/-benzo[ 5] thieno[2,3-d]azepine-2-carboxamide (412.9 g, 0.876 mol) in a mixture of pyridine (283 mL, 3.502 mol) and DCM (28920 mL) whilst maintaining the internal temp <40C (maximum temp reached 38C). The reaction was stirred at 18-25C for 1 hr after which time HPLC (sample quenched into methanol) indicated the reaction was complete (<1 % of aniline s/m remaining). Heptane (3300 mL) was added to the mixture at 18-25C and the resulting suspension was stirred for 15 min and the solids then collected by filtration. The filter cake was washed with heptane (2 x 1650 mL) and the crude solid so obtained was slurried in water (4130 mL) at 90- 95C for 30 min and then cooled to 18-25C.The solids were collected by filtration, washed with water (2 x 826 mL) and dried in a vacuum oven at 50C to give the title compound as a white solid (504.2 g, 92% active yield, HPLC purity [230 nm] 98.24%; containing 0.3% pyridine HCI by 1 H NMR and 0.4%. H20 by KF); R< 12.19 min; m/z 625.6 (M+H)+ (ES+).

Reference： [1]Patent: WO2016/55791,2016,A1 .Location in patent: Page/Page column 28

17
[ 66909-30-6 ]
N-(2-fluoro-6-methylphenyl)-6-(4-(5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)nicotinamido)benzoyl)-5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/55791,2016,A1
[2]Patent: WO2016/55791,2016,A1
[3]Patent: WO2016/55791,2016,A1

18
[ 66909-30-6 ]
ethyl 5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)nicotinate [ No CAS ]

Reference： [1]Patent: WO2016/55791,2016,A1
[2]Patent: WO2017/175000,2017,A1

19
[ 66909-30-6 ]
5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)nicotinic acid [ No CAS ]

Reference： [1]Patent: WO2016/55791,2016,A1
[2]Patent: WO2017/175000,2017,A1

20
[ 200122-34-5 ]
[ 66909-30-6 ]
ethyl 6-(4-(2-chloro-5-methylnicotinamido)benzoyl)-5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Ethyl 6-(4-(2-chloro-5-methylnicotinamido)benzoyl)-5,6-dihydro-4H-benzo[/3]thieno[2,3- cflazepine-2-carboxylate: Intermediate (Xa). To a suspension of <strong>[66909-30-6]2-chloro-5-methylnicotinic acid</strong> (2.49 g, 14.5 mmol) in DCM (50 mL) was added oxalyl chloride (4.24 mL, 48.4 mmol) and one drop of DMF. The resulting mixture was stirred at RT for 1 hr and was then evaporated in vacuo. The residue was taken up into DCM (25 mL) and added to a solution of ethyl 6-(4-aminobenzoyl)-5,6-dihydro-4/-/-benzo[£>] thieno[2,3-d]azepine-2-carboxylate (3.80 g, 9.68 mmol) in pyridine (20 mL) at RT. The reaction mixture was maintained at RT for 1 hr and then quenched by the addition of water (100 mL) and extracted with EtOAc (100 mL). The aq layer was separated and was washed with EtOAc (2 x 100 mL). The combined organic extracts were washed with water (100 mL), evaporated in vacuo and the resulting solid triturated with water (200 mL). This sequence was repeated on the same scale to afford the title compound as a pale yellow solid (10.0 g, 89% pure by HPLC, 95% yield); R< 2.51 min; m/z 545/547 (M+H)+ (ES+).
		To a suspension of <strong>[66909-30-6]2-chloro-5-methylnicotinic acid</strong> (2.49 g, 14.5 mmol) in DCM (50 mL) was added oxalyl chloride (4.24 mL, 48.4 mmol) and one drop of DMF. The resulting mixture was stirred at RT for 1 hr and the volatiles were evaporated in vacuo. The residue was taken up into DCM (25 mL) and added to a solution of ethyl 6-(4-aminobenzoyl)-5,6-dihydro-4/-/- benzo[6]thieno[2,3-c(]azepine-2-carboxylate (3.80 g, 9.68 mmol) in pyridine (20 mL) at RT. The mixture was maintained at RT for 1 hr and then quenched by the addition of water (100 mL) and extracted with EtOAc (100 mL). The aq layer was separated and was washed with EtOAc (2 x 100 mL). The combined organic extracts were washed with water (100 mL) and evaporated in vacuo. The resulting solid was triturated with water (200 mL) and dried in vacuo. This process was repeated on the same scale to afford the title compound as a pale yellow solid (10.0 g, 89% pure by HPLC, 95%); R' 2.51 min (Method 1 a); m/z 545/547 (M+H)+ (ES+). This material was used in subsequent steps without additional purification

Reference： [1]Patent: WO2016/55791,2016,A1 .Location in patent: Page/Page column 16
[2]Patent: WO2016/97761,2016,A1 .Location in patent: Page/Page column 40

21
[ 64-17-5 ]
[ 66909-30-6 ]
[ 894074-85-2 ]

Yield	Reaction Conditions	Operation in experiment
82%		Ethyl 2-chloro-5-methylnicotinate. To a solution of <strong>[66909-30-6]2-chloro-5-methylnicotinic acid</strong> (3.90 g, 22.7 mmol) in DCM (100 ml_) was added oxalyl chloride (9.95 ml_, 1 14 mmol) followed by 1 drop of DMF. The resulting mixture was stirred at RT for 30 min and evaporated in vacuo. The residue thus obtained was taken up into EtOH (66 ml_), stirred for a further 2 hr and then evaporated in vacuo. The crude product obtained was purified by flash column chromatography (S1O2, 120 g, 0-50% DCM in isohexane, gradient elution) to afford the title compound as a colourless oil (3.71 g, 82% yield); 1 H NMR delta: 1.32 (3H, t), 2.34 (3H, s), 4.34 (2H, q), 8.06-8.07 (1 H, m), 8.41-8.43 (1 H, m). [See also: Yamamoto S. et al., Bioorg. Med. Chem. 2012, 20, 422-434.]
82%		To a solution of <strong>[66909-30-6]2-chloro-5-methylnicotinic acid</strong> (3.90 g, 22.7 mmol) in DCM (100 mL) was added oxalyl chloride (9.95 mL, 114 mmol) followed by 1 drop of DMF. The resulting mixture was stirred at RT for 30 min and evaporated in vacuo. The residue thus obtained was taken up into EtOH (66 mL), stirred for a further 2 hr and then evaporated in vacuo. The crude product obtained was purified by flash column chromatography (S1O2, 120 g, 0-50% DCM in isohexane, gradient elution) to afford the title compound as a colourless oil (3.71 g, 82% yield); 1 H NMR delta: 1.32 (3H, t), 2.34 (3H, s), 4.34 (2H, q), 8.06-8.07 (1 H, m), 8.41 -8.43 (1 H, m). [See also: Yamamoto S. et al., Bioorg. Med. Chem. 2012, 20, 422-434.]

Reference： [1]Patent: WO2016/55791,2016,A1 .Location in patent: Page/Page column 12
[2]Patent: WO2017/175000,2017,A1 .Location in patent: Page/Page column 28

22
[ 66909-30-6 ]
ethyl 4-(4-(5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)nicotinamido)benzoyl)-5,6-dihydro-4H-dithieno[3,2-b:2',3'-d]alazepine-8-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/175000,2017,A1

23
[ 66909-30-6 ]
4-(4-(5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)nicotinamido)benzoyl)-5,6-dihydro-4H-dithieno[3,2-b:2',3'-d]azepine-8-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/175000,2017,A1

24
[ 66909-30-6 ]
N-(2,6-difluorophenyl)-4-(4-(5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)nicotinamido)benzoyl)-5,6-dihydro-4H-dithieno[3,2-b:2',3'-d]azepine-8-carboxamide [ No CAS ]

Reference： [1]Patent: WO2017/175000,2017,A1

25
[ 66909-30-6 ]
N-(2,6-difluorophenyl)-4-(4-(5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)nicotinamido)benzoyl-2,3,5,6-d₄)-5,6-dihydro-4H-dithieno[3,2-b:2',3'-d]azepine-8-carboxamide [ No CAS ]

Reference： [1]Patent: WO2017/175000,2017,A1

26
[ 66909-30-6 ]
2-chloro-5-methylnicotinoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; for 4h;Reflux;	In a 100 mL reaction flask,1.36 g (5 mmol) of <strong>[66909-30-6]2-chloro-5-methylnicotinic acid</strong>,Thionyl chloride 10 mL (0.141 mol),Ice bath cooling under stirring 30min,Heated to reflux reaction 3.5h,The remaining thionyl chloride was evaporated under reduced pressure,The resulting light yellow solid is2-Chloro-5-methylnicotinoyl chloride

Reference： [1]Patent: CN104672256,2017,B .Location in patent: Paragraph 0095-0096

27
[ 66909-30-6 ]
2-chloro-5-methylnicotinoyl isothiocyanate [ No CAS ]

Reference： [1]Patent: CN104672256,2017,B

28
[ 66909-30-6 ]
6-methyl-2-benzylamino-4H-pyrido[3,2-e][1,3]thiazin-4-one [ No CAS ]

Reference： [1]Patent: CN104672256,2017,B

29
[ 66909-30-6 ]
6-methyl-2-phenylamino-4H-pyrido[3,2-e][1,3]thiazin-4-one [ No CAS ]

Reference： [1]Patent: CN104672256,2017,B

30
[ 18368-64-4 ]
[ 66909-30-6 ]

Reference： [1]Patent: WO2007/108750,2007,A1

31
[ 66909-30-6 ]
(3S,4S)-4-(cyclohexylamino)-1-(5-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-2-yl)piperidin-3-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 1761 - 1780

32
[ 66909-30-6 ]
[ 118493-85-9 ]
5-(2-chloro-5-methylpyridin-3-yl)-3-methyl-1,2,4-oxadiazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 1761 - 1780

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{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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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
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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. 66909-30-6 ]

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[ 66909-30-6 ] Synthesis Path-Upstream 1~7

[ 66909-30-6 ] Synthesis Path-Downstream 1~32

Related Functional Groups of [ 66909-30-6 ]

Chlorides

Carboxylic Acids

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Pyridines

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