[ CAS No. 95652-80-5 ]

Name: 95652-80-5|2-Chloro-6-methoxynicotinaldehyde|98%
Brand: Ambeed
SKU: A246766
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Quality Control of [ 95652-80-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 95652-80-5 ]

Product Details of [ 95652-80-5 ]

CAS No. :	95652-80-5	MDL No. :	MFCD10697549
Formula :	C₇H₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QXHZQUBXMXEKMX-UHFFFAOYSA-N
M.W :	171.58	Pubchem ID :	13382638
Synonyms :

Calculated chemistry of [ 95652-80-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.13
TPSA :	39.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.8
Log Po/w (XLOGP3) :	1.58
Log Po/w (WLOGP) :	1.56
Log Po/w (MLOGP) :	0.52
Log Po/w (SILICOS-IT) :	2.12
Consensus Log Po/w :	1.52

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.17
Solubility :	1.16 mg/ml ; 0.00675 mol/l
Class :	Soluble
Log S (Ali) :	-2.01
Solubility :	1.66 mg/ml ; 0.00969 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.71
Solubility :	0.333 mg/ml ; 0.00194 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.77

Safety of [ 95652-80-5 ]

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 [ 95652-80-5 ]

* 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 [ 95652-80-5 ]
Downstream synthetic route of [ 95652-80-5 ]

[ 95652-80-5 ] Synthesis Path-Upstream 1~12

1
[ 17228-64-7 ]
[ 68-12-2 ]
[ 95652-80-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1 h; Stage #2: at -78℃; for 1.5 h; Stage #3: With acetic acid In tetrahydrofuran; pentane at 20℃; for 0.5 h;	Compound 5 was added (4.14 mL, 34.8 mmol) over 5 min to the solution of tert-butyllithium (1.7M in pentane, 22.5 mL, 38.3 mmol) in 69 mL of THF at -78 °C. The reaction mixture was stirred at -78 °C for 1 h, then dimethylformamide (3.5 mL, 45.0 mmol) was added and the mixture was stirred at -78 °C for 1.5 h. After the addition of glacial acetic acid (4.0 mL, 69.0 mmol) , the reaction mixture was allowed to warm to room temperature over a 30-min period and diethyl ether (200 mL) was added. The organic phase was washed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL) , and was dried over Na2S04. Concentration under reduced pressure afforded the product which was recrystallized from hexane to yield 4.6 g (76percent) of compound 6 as light yellow solid, mp: 67.0-68.0 °C; 1 H NMR (300 MHz, CDC13) δ[ ppm] : 10.29 (d, J=0.8 Hz, 1H) , 8.05 (d, J=7.9 Hz, 1H) , 7.02 (dd, Jl=7.9 Hz, J2=0.8 Hz, 1H) , 4.08 (s, 3H) ; 13C NMR (75 MHz, CDC13) δ [ppm] :188.0, 164.2, 154.6, 140.0, 117.6, 117.5, 54.8; IR V (ATR cm-1) : 3103, 2869, 1683, 1567, 1468, 1378, 1273, 1005.

Reference： [1] Patent: WO2017/118762, 2017, A1, . Location in patent: Page/Page column 40; 41

2
[ 777931-67-6 ]
[ 68-12-2 ]
[ 95652-80-5 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 7, p. 1980 - 1983
[2] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 7, p. 723 - 732

3
[ 38496-18-3 ]
[ 124-41-4 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Reference： [1] Patent: WO2013/130689, 2013, A1, . Location in patent: Paragraph 00931; 00932; 00933; 00934

4
[ 2402-78-0 ]
[ 95652-80-5 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 7, p. 1980 - 1983
[2] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 7, p. 723 - 732

5
[ 17228-64-7 ]
[ 95652-80-5 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 7, p. 1980 - 1983
[2] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 7, p. 723 - 732

6
[ 67-56-1 ]
[ 72648-12-5 ]
[ 58819-72-0 ]
[ 95652-80-5 ]
[ 95652-79-2 ]

Reference： [1] Tetrahedron Letters, 1984, vol. 25, # 49, p. 5693 - 5696
[2] Tetrahedron Letters, 1984, vol. 25, # 49, p. 5693 - 5696

7
[ 124-41-4 ]
[ 72648-12-5 ]
[ 58819-72-0 ]
[ 95652-80-5 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287

8
[ 2591-86-8 ]
[ 17228-64-7 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Reference： [1] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56

9
[ 124-41-4 ]
[ 40381-90-6 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
[2] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287

10
[ 38496-18-3 ]
[ 124-41-4 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Reference： [1] Patent: WO2013/130689, 2013, A1, . Location in patent: Paragraph 00931; 00932; 00933; 00934

11
[ 2591-86-8 ]
[ 17228-64-7 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Reference： [1] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56

12
[ 124-41-4 ]
[ 40381-90-6 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
[2] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287

[ 95652-80-5 ] Synthesis Path-Downstream 1~29

1
[ 2591-86-8 ]
[ 17228-64-7 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Reference： [1]Journal of Organometallic Chemistry,1991,vol. 406,p. 49 - 56

2
[ 67-56-1 ]
[ 72648-12-5 ]
[ 58819-72-0 ]
[ 95652-80-5 ]
[ 95652-79-2 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 5693 - 5696
[2]Tetrahedron Letters,1984,vol. 25,p. 5693 - 5696

3
[ 124-41-4 ]
[ 72648-12-5 ]
[ 58819-72-0 ]
[ 95652-80-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 283 - 287

4
[ 124-41-4 ]
[ 40381-90-6 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 283 - 287
[2]Journal of the Chemical Society. Perkin transactions I,1989,p. 283 - 287

Yield	Reaction Conditions	Operation in experiment
		(19-3) The 2-chloro-6-methoxy-3-pyridinecarboxaldehyde (137 mg, 0.8 mmol) obtained in (19-2) above, glycine thiophene amide (148 mg, 0.8 mmol), sodium acetate (anhydrous) (66 mg, 0.8 mmol) and acetic anhydride (1.5 mL) were added to a sealed tube, and the obtained mixture was then stirred at 90 C. for 3 hours in the sealed tube. Thereafter, the reaction solution was cooled to room temperature, and water (10 mL) was then added thereto while cooling on ice. The mixture was stirred at room temperature for 1 hour, and a crystal was then collected by filtration. The crystal was washed with water (50 mL) and was then dried under reduced pressure to obtain 213 mg of a rough crystal. Thereafter, 100 mg of the obtained rough crystal was purified by silica gel column chromatography (SiO2 10 g, hexane:ethyl acetate=95:5 to 80:20), so as to obtain 55 mg of the above-captioned compound. 1H-NMR (400 MHz, DMSO-d6, delta). 9.04 (d, J=8.7 Hz, 1H), 8.16 (d, J=4.9 Hz, 1H), 8.01 (d, J=3.8 Hz, 1H), 7.37 (dd, J=4.7, 3.9 Hz, 1H), 7.26 (s, 1H), 7.13 (d, J=8.7 Hz, 1H), 3.94 (s, 3H). ESI-MS m/z 321 (M+H)+.

6
water, ammonium chloride [ No CAS ]
[ 95652-80-5 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In N,N-dimethyl-formamide; toluene;	The 3-bromo-2-chloro-6-methoxy-pyridine (0.50 g, 2.26 mmol) obtained in (19-1) above was dissolved in toluene (dehydrated) (11 mL), and thereafter, n-butyllithium (1.46 mL, 2.3 mmol, 1.57 mmol/L hexane solution) was added dropwise to the solution at -78 C. in an argon atmosphere. The obtained mixture was stirred at the same temperature as described above for 30 minutes, and DMF (1.0 mL) was then added to the reaction solution. The obtained mixture was further stirred for 30 minutes. Thereafter, a saturated ammonium chloride water (20 mL) was slowly added to the reaction solution, and the temperature of the mixture was then increased to room temperature. The mixture was extracted with diethyl ether (20 mL) twice, and organic layers were gathered. The resultant was dried over anhydrous sodium sulfate and was then filtrated, followed by vacuum concentration. The obtained residue was purified by silica gel column chromatography (SiO2 30 g, hexane:ethyl acetate=95:5 to 80:20), so as to obtain 180 mg of 2-chloro-6-methoxy-3-pyridinecarboxaldehyde.

Reference： [1]Patent: US2011/294857,2011,A1

7
[ 38496-18-3 ]
[ 124-41-4 ]
[ 95652-80-5 ]
[ 95652-81-6 ]

Yield	Reaction Conditions	Operation in experiment
		Step A: 2,6-Dichloronicotinic acid (30g, 156.3 mmol) was dissolved in methanol (300 mL) at room temperature. Sodium ethoxide (5.4 M in MeOH, 781.3 mmol, 145 mL) was added slowly at the same temperature. The reaction mixture was stirred at 70 C for 5 hours and cooled to room temperature. The precipitated solid from reaction mixture was filtered off and the mother liquor was concentrated under vacuum. All solid collected was dissolved in water (300 mL) and the solution was acidified with 6N HC1 solution to pH 6 at 0 C. The aqueous layer was extracted with ethyl acetate five times. The combined organic layers were dried over MgS04. The organic layer was filtered off and concentrated to give a 1 : 1 mixture of 6-chloro-2- methoxynicotinic acid and 2-chloro-6-methoxynicotinic acid (20.22g, 69%). MS m/z 188 [M+H]+. Step B: The mixture obtained above (11.48g, 61.2 mmol) was dissolved in THF (50 mL) and cooled to 0 C. Borane-THF complex (1.0 M in THF, 200 mL) was added slowly at 0 C. The reaction mixture was stirred at room temperature for 1 hour and cooled back to 0 C. Aqueous 6N HC1 (15 mL) was added very slowly at 0 C. The aqueous layer was neutralized with a saturated NaHC03 solution to pH 7. Dichloromethane was added and the aqueous layer was extracted. The combined organic layers were dried over K2C03, filtered and concentrated under vacuum to yield 10.6 g of corresponding alcohols. The residue can be used directly in the oxidation step or purified on silica gel with the mixture of ethyl acetate and hexane. TLC Rf 0.31 (30% EtOAc in hexane). MS m/z 174 [M+H]+. The isolated alcohols (3.9g, 22.7 mmol) were dissolved in dichloromethane (110 mL) and cooled to 0 C. Dess-Martin Periodinane (11.6 g, 27.3 mmol) was added portionwise. The reaction mixture was stirred at 0 C for 30 min. The reaction was quenched with a saturated NaHC03 solution and extracted with dichloromethane. The combined organic layers were dried over K2C03, filtered and concentrated to give a mixture of 3.53 g of 6-chloro-2- methoxynicotinaldehyde and 2-chloro-6-methoxynicotinaldehyde (91%).

Reference： [1]Patent: WO2013/130689,2013,A1 .Location in patent: Paragraph 00931; 00932; 00933; 00934

8
[ 2402-78-0 ]
[ 95652-80-5 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

9
[ 777931-67-6 ]
[ 68-12-2 ]
[ 95652-80-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

10
[ 95652-80-5 ]
[ 1585241-83-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

11
[ 95652-80-5 ]
C₁₀H₁₃NO₅ [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

12
[ 95652-80-5 ]
[ 1585241-84-4 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

13
[ 95652-80-5 ]
[ 1585241-65-1 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

14
[ 95652-80-5 ]
[ 1585241-85-5 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

15
[ 95652-80-5 ]
[ 1585241-67-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

16
[ 95652-80-5 ]
[ 1585241-75-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

17
[ 95652-80-5 ]
[ 1585241-75-3 ]
tert-butyl 3-(5-(tert-butoxy)-3-(2-((4-methoxybenzyl)oxy)ethyl)-1-nitro-4,5-dioxopentan-2-yl)-6-methoxypicolinate [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983

18
[ 95652-80-5 ]
[ 1585241-87-7 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Organic Letters,2014,vol. 16,p. 1980 - 1983

19
[ 95652-80-5 ]
[ 1585241-76-4 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Organic Letters,2014,vol. 16,p. 1980 - 1983
[3]Organic Letters,2014,vol. 16,p. 1980 - 1983
[4]Organic Letters,2014,vol. 16,p. 1980 - 1983

20
[ 95652-80-5 ]
[ 1585241-88-8 ]

21
[ 95652-80-5 ]
[ 1585241-77-5 ]

22
[ 95652-80-5 ]
C₃₅H₄₀N₂O₁₀ [ No CAS ]
[ 1585241-97-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983

23
[ 95652-80-5 ]
[ 1585241-99-1 ]
C₂₉H₃₈N₂O₉ [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983

24
[ 201230-82-2 ]
[ 95652-80-5 ]
[ 71-36-3 ]
[ 1585241-64-0 ]

Yield	Reaction Conditions	Operation in experiment
4.75 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate; In toluene; at 20 - 100℃; for 18h;	To a stirred solution of 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.To a suspension of the crude material including 12and NaOAc (3.78 g, 46.1 mmol) in the 1 : 1 mixture of n-BuOH and toluene (total 120 mL) was added Pd(dppf) Cl2 (1.12 g, 1.54 mmol) at room temperature. The resulting mixture was stirred under ordinary CO pressure (balloon) at 100C for 18 h. The reaction was quenched with saturated aqueous NH4Cl, filtered through a pad of Celite and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, n-hexane-EtOAc=2 : 1) to afford 13(4.75 g, 65% 2 steps) as a yellow oil.13: IR (film, cm-1): 2963, 2876, 1721, 1692, 1595, 1481, 1337, 1277, 1261, 1219, 1138, 1072, 1022; 1H-NMR (CDCl3, 500 MHz) delta: 10.39 (s, 1H), 8.18 (d, J=8.50 Hz, 1H), 6.94 (d, J=8.50 Hz, 1H), 4.44 (t, J=6.80 Hz, 2H), 4.06 (s, 3H), 1.83-1.76 (m, 2H), 1.54-1.45 (m, 2H), 0.99 (t, J=7.37 Hz, 3H); 13C-NMR (CDCl3, 125 MHz) delta: 189.1, 166.1, 165.2, 150.7, 138.6, 125.9, 114.1, 66.3, 54.5, 30.5, 19.2, 13.7; HR-MS (ESITOF): Calcd for C12H15NO4Na [(M+Na)+] 260.0893. Found 260.0891.

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

25
[ 17228-64-7 ]
[ 95652-80-5 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1980 - 1983
[2]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

26
[ 95652-80-5 ]
C₃₀H₄₂N₂O₇ [ No CAS ]
C₃₀H₄₂N₂O₇ [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 723 - 732

27
[ 95652-80-5 ]
[ 76350-90-8 ]
2-methoxy-6-[(2-methyl-3-phenyl-phenyl)methoxy]pyridine-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With palladium diacetate; caesium carbonate; tert-butyl XPhos; In toluene; at 80℃; for 4h;Inert atmosphere; Sealed tube;	Palladium (II) acetate (0.08 g, 0.36 mmol) , caesium carbonate (2.23 g, 6.83 mmol), 2-di-tert-butylphosphino-2 ' , 4 ' , 6 ' - triisopropylbiphenyl (t-Butyl XPhos) (0.290 g, 0.68 mmol), compound 6 (0.59 g, 3.41 mmol), and 4 (0.88 g, 4.44 mmol) and toluene (30 mL) were combined and purged by a stream of argon for 3 minutes. The reaction was sealed and heated at 80 C for 4h. The mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography on silica gel using 0-60% ethyl acetate in hexane. The product was recrystallized from diethyl ether (488 mg, 35%). mp : 132.0-133.0 C; 1H NMR (600MHz, CDC13) delta [ppm] : 10.22 (d, J=0.8 Hz, 1H) , 8.06 (d, J=8.4 Hz, 1H) , 7.44-7.41 (m, 3H) , 7.37-7.34 (m, 1H) , 7.32-7.30 (m, 2H) , 7.28 (d, J=7.5 Hz, 1H) , 7.26 (m, 1H) , 6.45 (dd, Jl=8.4 Hz, J2=0.8 Hz, 1H) , 5.52 (s, 2H) , 4.08 (3H), 2.28 (s, 3H) ; 13C NMR (151 MHz, DMSO-d6) delta [ppm] : 187.8, 166.6, 165.2, 143.2, 142.0, 140.5, 135.0, 134.8, 130.5, 129.5, 128.7, 128.3, 127.1, 125.7, 112.5, 103.9, 67.8, 54.1, 16.5; IR V (ATR cm-1): 3063, 2961, 2870, 1671, 1591, 1460, 1330, 1277; HRMS (ESI-TOF) Calcd for C21H19N03Na [M+Na]+ : 356.1263; found [M+Na]+: 356.1256.

Reference： [1]Patent: WO2017/118762,2017,A1 .Location in patent: Page/Page column 41; 42

28
[ 95652-80-5 ]
[ 76350-90-8 ]
N-{2-[({2-methoxy-6-[(2-methyl-3-phenylphenyl)methoxy]pyridin-3-yl}methyl)amino]ethyl}acetamide hydrochloride [ No CAS ]

Reference： [1]Patent: WO2017/118762,2017,A1

29
[ 17228-64-7 ]
[ 68-12-2 ]
[ 95652-80-5 ]

Yield	Reaction Conditions	Operation in experiment
76%		Compound 5 was added (4.14 mL, 34.8 mmol) over 5 min to the solution of tert-butyllithium (1.7M in pentane, 22.5 mL, 38.3 mmol) in 69 mL of THF at -78 C. The reaction mixture was stirred at -78 C for 1 h, then dimethylformamide (3.5 mL, 45.0 mmol) was added and the mixture was stirred at -78 C for 1.5 h. After the addition of glacial acetic acid (4.0 mL, 69.0 mmol) , the reaction mixture was allowed to warm to room temperature over a 30-min period and diethyl ether (200 mL) was added. The organic phase was washed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL) , and was dried over Na2S04. Concentration under reduced pressure afforded the product which was recrystallized from hexane to yield 4.6 g (76%) of compound 6 as light yellow solid, mp: 67.0-68.0 C; 1 H NMR (300 MHz, CDC13) delta[ ppm] : 10.29 (d, J=0.8 Hz, 1H) , 8.05 (d, J=7.9 Hz, 1H) , 7.02 (dd, Jl=7.9 Hz, J2=0.8 Hz, 1H) , 4.08 (s, 3H) ; 13C NMR (75 MHz, CDC13) delta [ppm] :188.0, 164.2, 154.6, 140.0, 117.6, 117.5, 54.8; IR V (ATR cm-1) : 3103, 2869, 1683, 1567, 1468, 1378, 1273, 1005.

Reference： [1]Patent: WO2017/118762,2017,A1 .Location in patent: Page/Page column 40; 41

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Similarity: 0.68

Ethers

[ 1228898-61-0 ]

(2-Chloro-6-methoxypyridin-3-yl)methanol

Similarity: 0.82

[ 95652-81-6 ]

6-Chloro-2-methoxynicotinaldehyde

Similarity: 0.77

[ 25297-52-3 ]

2-Chloro-6-methoxy-4-methylpyridine

Similarity: 0.76

[ 34392-85-3 ]

3-Amino-2-chloro-6-methoxypyridine

Similarity: 0.74

[ 15855-06-8 ]

2-Chloro-6-methoxypyridine-4-carboxylic Acid

Similarity: 0.73

Related Parent Nucleus of
[ 95652-80-5 ]

Pyridines

[ 1228898-61-0 ]

(2-Chloro-6-methoxypyridin-3-yl)methanol

Similarity: 0.82

[ 95652-81-6 ]

6-Chloro-2-methoxynicotinaldehyde

Similarity: 0.77

[ 25297-52-3 ]

2-Chloro-6-methoxy-4-methylpyridine

Similarity: 0.76

[ 34392-85-3 ]

3-Amino-2-chloro-6-methoxypyridine

Similarity: 0.74

[ 15855-06-8 ]

2-Chloro-6-methoxypyridine-4-carboxylic Acid

Similarity: 0.73

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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 95652-80-5 ]

Quality Control of [ 95652-80-5 ]

Related Doc. of [ 95652-80-5 ]

Product Details of [ 95652-80-5 ]

Calculated chemistry of [ 95652-80-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 95652-80-5 ]

Application In Synthesis of [ 95652-80-5 ]

[ 95652-80-5 ] Synthesis Path-Upstream 1~12

[ 95652-80-5 ] Synthesis Path-Downstream 1~29

Related Functional Groups of [ 95652-80-5 ]

Chlorides

Aldehydes

Ethers

Related Parent Nucleus of [ 95652-80-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 95652-80-5 ]

Related Parent Nucleus of
[ 95652-80-5 ]