1340506-55-9|tert-Butyl 6-chloropyridazine-3-carboxylate| Ambeed

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Quality Control of [ 1340506-55-9 ] Purity: 97% SDS Specification

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Product Details of [ 1340506-55-9 ]

CAS No. :	1340506-55-9
Formula :	C₉H₁₁ClN₂O₂
M.W :	214.65
SMILES Code :	O=C(C1=NN=C(Cl)C=C1)OC(C)(C)C
MDL No. :	MFCD18897601
InChI Key :	MHTGBUQUDMBSRI-UHFFFAOYSA-N
Pubchem ID :	63840606

Safety of [ 1340506-55-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1340506-55-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1340506-55-9 ]

[ 1340506-55-9 ] Synthesis Path-Downstream 1~31

1
[ 1340506-55-9 ]
[ 1417696-35-5 ]

References: [1]Tetrahedron Letters,2013,vol. 54,p. 414 - 418.

2
[ 1340506-55-9 ]
[ 603-35-0 ]
C₂₇H₂₆N₃O₂P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; In dimethyl sulfoxide; at 120.0℃;	General procedure: A round bottom flask equipped with reflux condenser and magnetic stirring bar was charged with substituted heteroaryl chloride (5 mmol), sodium azide (10 mmol), triphenylphosphine (10 mmol) and DMSO (40 ml). The reaction mixture was stirred at 120 C. Reaction progress was monitored by TLC. In 3-5 hours starting material was disappeared and new product was confirmed by TLC. 1N HCl (8 mL) was added to the reaction mixture and continued to stir at 120 C for additional 1-2 hour. Reaction mixture was cooled to room temperature and diluted with 1N HCl (8 mL). The resulting mixture was poured into distilled water (100 mL) and aqueous layer was washed with EtOAc (2 X 50 mL) to remove triphenylphosphine oxide. Aqueous layer was slowly neutralized with saturated aqueous NaHCO3 solution and extracted with EtOAc (2 X 50 mL). The combined organic layers were washed with water (40 mL), brine(40 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford substituted heteroaryl amine with high purity without column purification (purity was achieved in some products by washing solid compound with n-Pantane).

References: [1]Tetrahedron Letters,2013,vol. 54,p. 414 - 418.

3
[ 5049-61-6 ]
[ 1340506-55-9 ]
C₁₃H₁₅N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Inert atmosphere;	A suspension of (2) (1.38g, 6.41 mmol), 2-aminopyrazine (508mg, 5.34mmol), Cs2C03 (3.49g, 1.14mmol) and Xantphos (185mg, 0.32mmol) in dioxane (40ml_) was purged with Ar(g) for 10min. Pd2(dba)3 (147mg, 0.16mmol) was added and mixture was heated up to 90C overnight. Once cooled down to rt, it was poured into H20 (40ml_) and EtOAc (6 x 20ml_). The combined organics were washed dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel column chromatography with hexane/CH2CI2 (1 :0-0: 1 ) then CH2CI2/MeOH (1 :0-49: 1) yielded (3) as an off-white solid (752mg, 52%). (0881) LCMS (ES): Found 274.0 [M+Hf. (0882) 1H NMR (300 MHz, DMSO-cf6), d: 10.98 (s, 1 H), 9.01 (d, J=1.5 Hz, 1 H), 8.29- 8.39 (m, 1 H), 8.16-8.27 (m, 2H), 8.07 (d, J= 9.3 Hz, 1 H), 1.59 (s, 9H).

References: [1]Patent: WO2019/166824,2019,A1 .Location in patent: Page/Page column 114; 115.

4
[ 5096-73-1 ]
[ 24424-99-5 ]
[ 1340506-55-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; In tetrahydrofuran; at 50.0℃; for 1.0h;	A suspension of (1) (2.0g, 12.7mmol) and 4-(dimethylamino)pyridine (776mg, 6.3mmol) in THF (50ml_) was treated with di-fe/f-butyl dicarbonate (3.6g, 16.5mmol). It was heated up to 50C for 1 h, then stirred at rt overnight. The reaction mixture was concentrated in vacuo, re-dissolved in EtOAc (20ml_), poured into HCI solution (1 M, 20ml_) and extracted with EtOAc (2 x 20ml_). The combined organics were washed with NaHC03 solution (50ml_) and brine (50ml_), dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel column chromatography with hexane/EtOAc (1 :0-3: 1 ) yielded (2) as a white solid (2.2g, 81 %). (0878) LCMS (ES): Found 237.0 [M+Naf. (0879) 1H NMR (300 MHz, Chloroform-cf), d: 8.08 (d, J= 8.7 Hz, 1 H), 7.63 (d, J=8.9 Hz, 1 H), 1.67 (s, 9H).
56%	With dmap; In dichloromethane; at 20.0℃; for 12.0h;	Dissolve 6-chloropyridazine-3-carboxylic acid (7a) (2g, 12.62mmol) in 20mL DCM, add DMAP (3.08g, 25.23mmol),(Boc)2O (5.51g, 25.23mmol) was added at room temperature, and the reaction was stirred at room temperature for 12h.The solvent was removed under reduced pressure, and the residue was separated and purified by silica gel column chromatography (ethyl acetate/petroleum ether (v/v)=10/1-3/1),The tert-butyl 6-chloropyridazine-3-carboxylate (7b) (1.5 g, yield: 56%) was obtained.

References: [1]Patent: WO2019/166824,2019,A1 .Location in patent: Page/Page column 114; 115.
[2]Patent: CN112010858,2020,A .Location in patent: Paragraph 0568-0577.

5
[ 1340506-55-9 ]
6-[(pyrazin-2-yl)({5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophen-2-yl}methyl)amino]pyridazine-3-carboxylic acid [ No CAS ]