[ CAS No. 488149-34-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 488149-34-4 * Storage: {[proInfo.prStorage]}

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ 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) ]}	Inquiry {[ 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 -

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 488149-34-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 488149-34-4 ]

SDS Specification

Alternatived Products of [ 488149-34-4 ]

Product Details of [ 488149-34-4 ]

CAS No. :	488149-34-4	MDL No. :	MFCD11847245
Formula :	C₈H₉ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	200.62	Pubchem ID :	-
Synonyms :

Safety of [ 488149-34-4 ]

Signal Word:	Class:	N/A
Precautionary Statements:	UN#:	N/A
Hazard Statements:	Packing Group:	N/A

Application In Synthesis of [ 488149-34-4 ]

* 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 [ 488149-34-4 ]
Downstream synthetic route of [ 488149-34-4 ]

[ 488149-34-4 ] Synthesis Path-Upstream 1~4

1
[ 488149-34-4 ]
[ 676-58-4 ]
[ 55676-21-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: at 0℃; for 1 h; Stage #2: With water In tetrahydrofuran	A solution of 2-chloro-N-methoxy-N-methyl-nicotinamide (23.6 g, 118 mmol) in tetrahydrofuran (350 mL, 0.34M) at 0° C. was treated dropwise via an addition funnel with methyl magnesium chloride (3.0M solution in tetrahydrofuran, 100 mL, 300 mmol). The reaction became a very thick opaque white mixture and was diluted with additional tetrahydrofuran (150 mL). The reaction was stirred at 0° C. for 1 h. At this time, the reaction was carefully quenched with water (250 mL) and then partitioned between additional water (250 mL) and ethyl acetate (250 mL). The aqueous layer was back extracted with ethyl acetate (2*250 mL). The combined organics were washed with a saturated aqueous sodium chloride solution (250 mL), dried over magnesium sulfate, filtered, rinsed with ethyl acetate, and concentrated in vacuo. Flash chromatography (AnaLogix Intelliflash 280, 400 g silica gel column, 25-50percent ethyl acetate/hexanes) afforded 1-(2-chloro-pyridin-3-yl)-ethanone (13.17 g, 72percent) as a yellow oil.

Reference： [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 9, p. 764 - 768
[2] Patent: US2012/258982, 2012, A1, . Location in patent: Page/Page column 41

2
[ 488149-34-4 ]
[ 917-54-4 ]
[ 55676-21-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 0℃; for 1 h;	To a solution of 2 (473 mg, 3.0 mmol) in THF (8 mL) was added phenylethynyllithium, generated from phenylacetylene (306 mg, 3.0 mmol) and methyllithium (1.5 M in Et2O, 2.0 mL, 3.0 mmol) for 0.5 h at 0 C, or methyllithium (1.5 M in Et2O, 2.0 mL, 3.0 mmol) at 0 C. After being stirred for 0.5 h, the mixture was quenched with 0.5 N HCl (5 mL) and THF was evaporated in vacuo. The mixture was poured into 0.1 N HCl (30 mL) and extracted with dichloromethane(3 × 20 mL). The condensed residue was purified by silicagel column chromatography using 30percent EtOAc/n-hexane or vacuum distillation using a Kugelrohr apparatus to give 3a (616 mg, 85percent) and 6 (420 mg, 90percent), respectively.
90%	for 0.5 h;	Phenylacetylene (306 mg, 3.0 mmol) and methyl lithium (1.5 M in Et2O, 2.0 mL, 3.0 mmol) were reacted at 0 C for 0.5 hour Was added to a solution of compound 2 (473 mg, 3.0 mmol) in THF (8 mL). For 0.5 hours After mixing, the reaction was quenched by the addition of 0.5 N HCl (5 mL) and THF to the mixture and evaporated in vacuo. evaporation The resulting mixture was taken up in 0.1 N HCl (30 mL) and extracted with dichloromethane (3 x 20 mL). The concentrated residue was dissolved in 30percent The residue was purified by silica gel column chromatography using EtOAc / n-hexane as an extraction solvent to obtain Compound 3a (616 mg, 85percent) Respectively. Also, methyllithium (1.5 M in Et2O, 2.0 mL, 3.0 mmol) was added to a solution of compound 2 (473 mg, 3.0 mmol). After mixing for 0.5 h, the reaction was stopped by adding 0.5 N HCl (5 mL) to the mixture THF was evaporated in vacuo. The evaporated mixture was poured into 0.1 N HCl (30 mL) and added with dichloromethane (3 x 20 mL) . The concentrated residue was vacuum distilled using a Kugelrohr distillation column to yield compound 6 (420 mg, 90percent).

Reference： [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 7, p. 1908 - 1911
[2] Patent: KR101766414, 2017, B1, . Location in patent: Paragraph 0078; 0079; 0081

3
[ 488149-34-4 ]
[ 75-16-1 ]
[ 55676-21-6 ]

Reference： [1] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 311 - 322
[2] Patent: WO2016/132134, 2016, A1, . Location in patent: Page/Page column 74

4
[ 488149-34-4 ]
[ 116834-96-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 311 - 322

[ 488149-34-4 ] Synthesis Path-Downstream 1~10

1
[ 2942-59-8 ]
[ 6638-79-5 ]
[ 488149-34-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 72h;
93%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 72h;	3-(4-Carboxy-benzyl)-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester A solution of 2-chloronicotinic acid (20.0 g, 127 mmol) in N,N-dimethylformamide (600 mL, 0.21M) was treated with N,N-diisopropylethylamine (66 mL, 379 mmol), N,O-dimethylhydroxylamine hydrochloride (13.63 g, 140 mmol), and benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (84.25 g, 190 mmol). The reaction was stirred at 25° C. over 3 d. The resulting reaction was concentrated in vacuo, taken up in ethyl acetate (400 mL) and washed with a saturated aqueous ammonium chloride solution (2250 mL), a saturated aqueous sodium bicarbonate solution (2250 mL), and a saturated aqueous sodium chloride solution (250 mL). The organics were dried over magnesium sulfate, filtered and rinsed with ethyl acetate, and concentrated in vacuo. Flash chromatography (AnaLogix IntelliFlash 280 column chromatography, 400 g silica gel column, 25-50% ethyl acetate/hexanes) afforded 2-chloro-N-methoxy-N-methyl-nicotinamide (23.58 g, 93%) as a light yellow oil.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide	V.1.A Example V-I; l-{3-[3-(3-fluorophenyl)-l//-pyrazol-5-yl]pyridin-2-yl}piperidine-4-carbonitrile; Step A: 2-chloro-iV-methoxy-N-methylnicotinamide; The mixture of 2-chloronicotinic acid (3.16 g, 20.1 mmol), ν,O- dimethylhydroxylamine hydrochloride (2.15 g, 22.1 mmol), HOBT (1.53 g, 10.0 mmol), EDC (4.61 g, 24.1 mmol) and trimethylamine (6.1 g, 60.2 mmol) in DMF (100 mL) was stiired overnight. Diluted with water and extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by silica gel chromotography (20%-30% EtOAc in hexane). LRMS: m/z found = 201.1 (M+l).

10.5 g

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;

8.A A) 2-Chloro-N-methoxy-N-methylpyridine-3-carboxamide 2-Chloropyridine-3-carboxylic acid (13 g), N,O-dimethylhydroxylamine hydrochloride (8.85 g), HOBt (5.57 g), EDCI (15.37 g) and triethylamine (34.5 ml) were dissolved in DMF (150 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) to give the title compound (10.5 g). [0490] MS (API+): [M+H]+ 201.0. [0491] 1H NMR (300 MHz, DMSO-d6) δ 3.33 (3H, s), 3.47 (3H, s), 7.45-7.63 (1H, m), 7.98-8.08 (1H, m), 8.44-8.55 (1H, m).

Reference： [1]Haynes, Nancy-Ellen; Scott, Nathan R.; Chen, Li C.; Janson, Cheryl A.; Li, Jia Kui; Lukacs, Christine M.; Railkar, Aruna; Tozzo, Effie; Whittard, Toni; Brown, Nicholas F.; Cheung, Adrian Wai-Hing [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 9, p. 764 - 768]
[2]Current Patent Assignee: ROCHE HOLDING AG - US2012/258982, 2012, A1 Location in patent: Page/Page column 40-41
[3]Current Patent Assignee: MERCK & CO INC - WO2009/51705, 2009, A1 Location in patent: Page/Page column 48-47
[4]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2013/331409, 2013, A1 Location in patent: Paragraph 0489-0491

2
[ 49609-84-9 ]
Ν,Ο-dimethylhydroxylamine hydrochloride [ No CAS ]
[ 488149-34-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With bicarbonate In tetrahydrofuran at 20℃; for 0.5h;	30.A 2-Chloronicotinoyl chloride (36 g, 0.20 mol) was dissolved in tetrahydrofuran (290 mL) and separately N,0-dimethylhydroxylamine hydrochloride (48 g, 0.49 mol) was stirred in 290 mL saturated bicarbonate solution until the degassing subsided. Then the bicarbonate solution was added to the acid chloride solution and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with ethyl acetate (2x), dried over sodium sulfate, filtered and evaporated to give the desired product (34 g, 83%). LCMS for C8Hi0Cl 2O2 (M+H)+: m/z = 201.0; Found: 200.9.

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2011/130342, 2011, A1 Location in patent: Page/Page column 100

3
[ 49609-84-9 ]
[ 6638-79-5 ]
[ 488149-34-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In dichloromethane at 10 - 15℃; Inert atmosphere;	2-Chloro-N-methoxy-N-methylnicotinamide^2;3 3a A solution of 2-chloronicotinoyl chloride 2a (25.00 g, 142 mmol) in DCM (750 mL) was cooled to 10 °C (internal temperature) with stirring. Triethylamine (99.0 mL, 71.80 g, 710 mmol) was added over 5 minutes, followed by portionwise addition of solid N,O-dimethylhydroxylamine hydrochloride (15.24 g, 156 mmol) at such a rate as to maintain the temperature below 15 °C. After the addition was complete, the mixture was stirred under a nitrogen atmosphere for 2.5 h. NaHCO3 (sat. aq; 750 mL) was added cautiously with vigorous stirring, and the biphasic mixture stirred for 30 minutes. The layers were separated, and the aqueous layer extracted with further DCM (100 mL). The DCM layers were combined, dried (MgSO4), and evaporated in vacuo to give 3a (23.74 g, 83%) as a tan-coloured powder; mp 77 - 83 °C; H(DMSO-d6) 8.50 (1H, dd, J 4.8, 1.8 Hz), 8.00 (1H, dd, J 7.4, 1.8 Hz), 7.52 (1H, dd, J 7.4, 4.8 Hz), 3.78 (0.4H, br s), 3.46 (2.6H, s), 3.30 (2.4H, s) and 3.10 (0.6H, br s); LCMS (Method A): rt 0.75 mins; m/z 201 (100 %; [M+H]+).

Reference： [1]Roughley, Stephen D.; Browne, Helen; MacIas, Alba T.; Benwell, Karen; Brooks, Teresa; D'Alessandro, Jalanie; Daniels, Zoe; Dugdale, Sarah; Francis, Geraint; Gibbons, Ben; Hart, Terance; Haymes, Timothy; Kennett, Guy; Lightowler, Sean; Matassova, Natalia; Mansell, Howard; Merrett, Angela; Misra, Anil; Padfield, Anthony; Parsons, Rachel; Pratt, Robert; Robertson, Alan; Simmonite, Heather; Tan, Kiri; Walls, Steven B.; Wong, Melanie [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 901 - 906]

4
[ 488149-34-4 ]
[ 873-77-8 ]
[ 85-29-0 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 5 - 25℃;Inert atmosphere;	General procedure: A solution of 3a (23.74 g, 118.33 mmol) was dissolved in dry THF (500 mL) in a 3-necked flask equipped with thermometer, nitrogen bubbler and pressure-equalising dropping funnel. The flask was purged with nitrogen, and cooled to 5 C (internal temperature). The dropping funnel was charged with 4-chlorophenylmagnesium bromide (1.0 M in Et2O; 153.8 mL, 153.80 mmol) and the reagent added to the reaction flask dropwise over 15 minutes, during which time the temperature rose to 8 C. Stirring was continued for 19 h, during which time the temperature rose to ambient. Hydrochloric acid (2.0 M in H2O; 400 mL) was added slowly and the mixture stirred vigorously for 30 minutes. The mixture was adjusted to pH 8 by cautious addition of solid NaHCO3, water (500 mL) added, and the mixture extracted with EtOAc (3 × 500 mL). The organic extracts were washed successively with water (500 mL) and brine (500 mL), combined, dried (MgSO4) and evaporated to dryness to give the ketone 4a (29.8 g, 100%) as a yellow oil.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 901 - 906

5
[ 2942-59-8 ]
Ν,Ο-dimethylhydroxylamine hydrochloride [ No CAS ]
[ 488149-34-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 2-chloronicotinic acid With thionyl chloride In benzene for 3h; Reflux; Stage #2: Ν,Ο-dimethylhydroxylamine hydrochloride With pyridine In dichloromethane; benzene at 20℃; Cooling with ice;	1.1 [Step 1] 5.0 g of 2-chloronicotinic acid and 2.8 mL of thionyl chloride were dissolved in 60 mL of benzene and then refluxed while heating. Three hours later, after adding the reaction liquid to 50 mL of a separately prepared dichloromethane solution containing 4.6 g of N,O-dimethylhydroxyamine hydrochloride and 20 mL of pyridine while cooling with ice, the solution was stirred overnight at room temperature. Following completion of the reaction, the solution was concentrated under reduced pressure, and the resulting residue was purified by recrystallization (with a mixture of ethyl acetate and hexane) to obtain 5.1 g of 2-chloro-N-methoxy-N-methylnicotinamide in the form of pale yellow crystals (79%).
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃;	49 Preparative Cornpound 49: 2-chloro-N-rnethoxy-N-rnethyl-pyridine-3-carboxarnide A suspension of N-methoxymethanamine hydrochloride (0.743g, 7.62mmol) and 2- chloropyridine-3-carboxylic acid (lg, 6.35mmol) in DCM (lOmL) was treated with DIPEAat R.T. (2.46g, 19.O42mmol). A 50% solution of propyl phosphonic anhydride in EtOAc (6.OmL, lOmmol) was then added drop wise and the reaction stirred at R.T. overnight. The mixture was treated with aqueous sodium bicarbonate solution and vigorously stirred for 30 mm. The phases were separated and the aqueous layer was extracted with DCM (2 x 5OmL)). The combined organic layers were washed with deionized water (4OmL),dried using magnesium sulphate and concentrated under reduced pressure to give titlecompound as a white solid. The solid was confirmed as desired product by LCMS M+H201 (R 1.8 mm.) and 1H NMR (500MHz CDCI3) O 8.21 (1 H, d, J= 7.1 Hz, ArH), 7.47(1H, d, J = 3.3 Hz, ArH), 7.10(1 H, m, J = 5.1 Hz, ArH), 3.26 (3 H, s, OMe), 3.17(3 H, s,N Me).

Reference： [1]Current Patent Assignee: KOWA COMPANY, LTD. - EP2412710, 2012, A1 Location in patent: Page/Page column 28
[2]Current Patent Assignee: UNIVERSITY OF DUNDEE - WO2016/132134, 2016, A1 Location in patent: Page/Page column 73; 74

6
[ 488149-34-4 ]
[ 676-58-4 ]
[ 55676-21-6 ]

Yield	Reaction Conditions	Operation in experiment
72%		A solution of 2-chloro-N-methoxy-N-methyl-nicotinamide (23.6 g, 118 mmol) in tetrahydrofuran (350 mL, 0.34M) at 0° C. was treated dropwise via an addition funnel with methyl magnesium chloride (3.0M solution in tetrahydrofuran, 100 mL, 300 mmol).The reaction became a very thick opaque white mixture and was diluted with additional tetrahydrofuran (150 mL).The reaction was stirred at 0° C. for 1 h.At this time, the reaction was carefully quenched with water (250 mL) and then partitioned between additional water (250 mL) and ethyl acetate (250 mL).The aqueous layer was back extracted with ethyl acetate (2*250 mL).The combined organics were washed with a saturated aqueous sodium chloride solution (250 mL), dried over magnesium sulfate, filtered, rinsed with ethyl acetate, and concentrated in vacuo.Flash chromatography (AnaLogix Intelliflash 280, 400 g silica gel column, 25-50percent ethyl acetate/hexanes) afforded 1-(2-chloro-pyridin-3-yl)-ethanone (13.17 g, 72percent) as a yellow oil.

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 764 - 768
[2]Patent: US2012/258982,2012,A1 .Location in patent: Page/Page column 41

7
[ 488149-34-4 ]
[ 116834-96-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 57,p. 311 - 322

8
[ 488149-34-4 ]
[ 75-16-1 ]
[ 55676-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; diethyl ether; at -10 - 20℃; for 12.0833h;	A solution of preparative compound 49, 2-chloro-N-methoxy-N-methyl-pyridine-3- carboxamide (1.27g, 6.3lmmol) in THF (lOmL) was cooled in an ice/salt bath to about - 10°C. A 3M solution of methyl magnesium bromide in diethyl ether (1.13g, 9.47mmol) was then added drop wise to the cooled reaction over 5 minutes. The reaction mixture was allowed to warm to R.T. and stirred for l2hrs. The reaction mixture was thenquenched with 3 M HCI (2OmL), and stirred for 30 minutes at R.T. Reaction mixture was then partitioned between diethyl ether (5OmL) and 3M HCI (lOmL). The organic phase was washed with aqueous sodium bicarbonate and saturated sodium chloride, dried using magnesium sulphate and concentrated under reduced pressure to give title compound. The product was confirmed by LCMS M+H 156 (R 2.5 mm.) and 1H NMR(500MHz MeOD) O 8.47 (1 H, dd, J = 4.8 Hz, ArH), 8.05 (1 H, dd, J = 7.6 Hz, ArH), (1 H, dd, J = 4.8 Hz, ArH), 2.64 (3 H, s, Me).

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 57,p. 311 - 322
[2]Patent: WO2016/132134,2016,A1 .Location in patent: Page/Page column 74

9
[ 2942-59-8 ]
[ 30289-28-2 ]
[ 488149-34-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; triethylamine; In acetonitrile;	2N-methylcarbamoyl chloride and triethylamine in the presence of 0.05 equivalents of 4- (dimethylamino) pyridine (4-DMAP) in acetonitrile in dichloromethane (Compound 2) was prepared in a yield of 83%.

Reference： [1]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 1908 - 1911
[2]Patent: KR101766414,2017,B1 .Location in patent: Paragraph 0078; 0080

10
[ 488149-34-4 ]
[ 917-54-4 ]
[ 55676-21-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; diethyl ether; at 0℃; for 1h;	To a solution of 2 (473 mg, 3.0 mmol) in THF (8 mL) was added phenylethynyllithium, generated from phenylacetylene (306 mg, 3.0 mmol) and methyllithium (1.5 M in Et2O, 2.0 mL, 3.0 mmol) for 0.5 h at 0 C, or methyllithium (1.5 M in Et2O, 2.0 mL, 3.0 mmol) at 0 C. After being stirred for 0.5 h, the mixture was quenched with 0.5 N HCl (5 mL) and THF was evaporated in vacuo. The mixture was poured into 0.1 N HCl (30 mL) and extracted with dichloromethane(3 × 20 mL). The condensed residue was purified by silicagel column chromatography using 30percent EtOAc/n-hexane or vacuum distillation using a Kugelrohr apparatus to give 3a (616 mg, 85percent) and 6 (420 mg, 90percent), respectively.
90%	In tetrahydrofuran; dibutyl ether; for 0.5h;	Phenylacetylene (306 mg, 3.0 mmol) and methyl lithium (1.5 M in Et2O, 2.0 mL, 3.0 mmol) were reacted at 0 C for 0.5 hour Was added to a solution of compound 2 (473 mg, 3.0 mmol) in THF (8 mL). For 0.5 hours After mixing, the reaction was quenched by the addition of 0.5 N HCl (5 mL) and THF to the mixture and evaporated in vacuo. evaporation The resulting mixture was taken up in 0.1 N HCl (30 mL) and extracted with dichloromethane (3 x 20 mL). The concentrated residue was dissolved in 30percent The residue was purified by silica gel column chromatography using EtOAc / n-hexane as an extraction solvent to obtain Compound 3a (616 mg, 85percent) Respectively. Also, methyllithium (1.5 M in Et2O, 2.0 mL, 3.0 mmol) was added to a solution of compound 2 (473 mg, 3.0 mmol). After mixing for 0.5 h, the reaction was stopped by adding 0.5 N HCl (5 mL) to the mixture THF was evaporated in vacuo. The evaporated mixture was poured into 0.1 N HCl (30 mL) and added with dichloromethane (3 x 20 mL) . The concentrated residue was vacuum distilled using a Kugelrohr distillation column to yield compound 6 (420 mg, 90percent).

Reference： [1]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 1908 - 1911
[2]Patent: KR101766414,2017,B1 .Location in patent: Paragraph 0078; 0079; 0081

Same Skeleton Products

Related Products

Historical Records

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. 488149-34-4 ] {[proInfo.proName]}

Quality Control of [ 488149-34-4 ]

Related Doc. of [ 488149-34-4 ]

Product Details of [ 488149-34-4 ]

Safety of [ 488149-34-4 ]

Application In Synthesis of [ 488149-34-4 ]

[ 488149-34-4 ] Synthesis Path-Upstream 1~4

[ 488149-34-4 ] Synthesis Path-Downstream 1~10

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry