76593-36-7|6-Chloro-4,5-dimethylpyridazin-3-amine| Ambeed

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Quality Control of [ 76593-36-7 ] Purity: 98% SDS Specification

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Product Details of [ 76593-36-7 ]

CAS No. :	76593-36-7
Formula :	C₆H₈ClN₃
M.W :	157.60
SMILES Code :	CC1=C(C)C(N)=NN=C1Cl
MDL No. :	MFCD00828815
InChI Key :	NYQKWJMDQIXMEE-UHFFFAOYSA-N
Pubchem ID :	6991943

Safety of [ 76593-36-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332-H335
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P322-P330-P332+P313-P337+P313-P340-P362-P363-P403-P403+P233-P405-P501

Application In Synthesis of [ 76593-36-7 ]

* 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 [ 76593-36-7 ]

[ 76593-36-7 ] Synthesis Path-Downstream 1~35

1
[ 23130-84-9 ]
[ 76593-36-7 ]

References: [1]Synthesis,1980,p. 830 - 831.

2
[ 4637-24-5 ]
[ 76593-36-7 ]
[ 51519-08-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1447 - 1457.

5
[ 34584-69-5 ]
[ 76593-36-7 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 350 - 361.

6
[ 76593-36-7 ]
[ 183610-69-7 ]
[ 328554-59-2 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 350 - 361.

7
[ 76593-36-7 ]
3-(4-fluoro-phenyl)-2-(4-methanesulfonyl-phenyl)-7,8-dimethyl-imidazo[1,2-<i>b</i>]pyridazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 350 - 361.

8
[ 76593-36-7 ]
[ 51519-28-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1447 - 1457.

9
[ 76593-36-7 ]
7,8-dimethyl-6-(2,2-dimethyl-3-sulfamoyl-1-propoxy)[1,2,4]triazolo[1,5-b]pyridazine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1447 - 1457.

10
[ 76593-36-7 ]
2-(7,8-Dimethyl-[1,2,4]triazolo[1,5-b]pyridazin-6-yloxymethyl)-2-ethyl-butane-1-sulfonic acid amide [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1447 - 1457.

Yield	Reaction Conditions	Operation in experiment
		5-Dimethylamino-N-(6-chloro-4,5-dimethyl-3-pyridazinyl)-1-naphthalenesulphonamide, m.p. 229-231 C.; mass spectrum (+ve FAB, DMSO/dichloromethane/NBA): 391 (M+H)+; starting from 3-amino-6-chloro-4,5-dimethylpyridazine, which was obtained by the procedure described in J. Pharm. Soc. (Japan), 1962, 82, 233;

12
[ 76593-36-7 ]
[ 403-29-2 ]
[ 1095708-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 16.0h;Reflux;	Step 3.1. 6-chloro-2-(4-fluorophenyl)-7,8-dimethylimidazo[1,2-b]pyridazine The mixture of 13.0 g (82.5 mmol) of 6-chloro-4,5-dimethylpyridazin-3-ylamine and 23.2 g (107 mmol) of 2-bromo-1-(4-fluorophenyl)ethanone in 130 ml of ethanol is refluxed for 16 hours. The solvent is evaporated off under reduced pressure, and the residue is taken up with chloroform and washed with a dilute solution of aqueous ammonia. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. The brown solid obtained is triturated in acetone, to give 19.2 g of a beige powder after filtration and drying. Mp: 172-174 C. 1H NMR (CDCl3) δ: 8.10 (s, 1H); 8.00 (pseudo dd, 1H); 7.15 (pseudo t, 1H); 2.70 (s, 3H); 2.4 (s, 3H) ppm

References: [1]Patent: US2010/152157,2010,A1 .Location in patent: Page/Page column 10.

13
[ 71827-48-0 ]
[ 76593-36-7 ]
[ 1095708-20-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	In ethanol; for 16.0h;Reflux;	Step 2.1. 6-Chloro-2-(4-fluorophenyl)-7,8-dimethylimidazo[1,2-b]pyridazine A solution of 13 g (85 mmol) of 3-amino-6-chloro-4.5-dimethylpyridazine and 23 g (107 mmol) of 2-bromo-1-(4-fluorophenyl)ethanone in 130 mL of ethanol is refluxed for 16 hours. After cooling, the solvent is evaporated off under reduced pressure and the residue is taken up in chloroform. The organic phase is washed with diluted aqueous ammonia, dried over sodium sulfate and concentrated under reduced pressure to give a brown solid. This solid is triturated in acetone to give 19.2 g of a beige-colored powder. Yield: 84% m.p.: 172-174 C. 1H NMR (CDCl3) δ: 8.10 (s, 1H), 7.95 (m, 2H), 7.15 (pseudo t, 2H), 2.70 (s, 3H), 2.45 (s, 3H) ppm.

References: [1]Patent: US2010/179154,2010,A1 .Location in patent: Page/Page column 24.

14
[ 67-56-1 ]
[ 201230-82-2 ]
[ 76593-36-7 ]
methyl 6-amino-4,5-dimethylpyridazine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 20 - 100℃; under 6750.68 Torr; for 0.5h;	A mixture of <strong>[76593-36-7]6-chloro-4,5-dimethylpyridazin-3-amine</strong> (CAS-Nr.76593-36-7, 1 .00 g, 6.35 mmol, 1 .0 eq), [1 ,1 ,-bis-(diphenylphosphino)ferrocene]-palladium(ll) dichloride (1 .04 g, 1 .27 mmol, 0.2 eq) and triethylamine (973 μΙ_, 6.98 mmol, 1 .1 eq) was placed in 90 mL autoclave and dissolved in 1 1 .3 mL MeOH/THF (10/1 ). The autoclave was flushed with carbon monoxide (3x) and was then pressurized with carbon monoxide to 9 bar. The reaction mixture was stirred for 30 min at RT. The carbon monoxide was released and the autoclave was then degassed by the use of high vacuum. The autoclave was again pressurized to 9 bar with carbon monoxide and subsequently heated to 100 . In the course of the reaction, carbon monoxide consumption was observed (decrease of CO pressure). The autoclave was cooled to rt, and after release of carbon monoxide flushed with inert gas. The reaction mixture was filtered through a small pad of Celite. The crude mixture was purified via MPLC (Biotage Isolera; 50 g SNAP cartridge: DCM-> DCM/ethanol 95/5) to give 1 .28 g (95% yield) of the title compound in 85% purity (UPLC, area-%).UPLC-MS (Method 2): RT = 0.62 min; m/z = 182 (M+H) +.

References: [1]Patent: WO2012/136776,2012,A1 .Location in patent: Page/Page column 112-113.

15
[ 141-52-6 ]
[ 76593-36-7 ]
[ 1402609-45-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	In ethanol; at 130℃; for 2.0h;Microwave irradiation;	6-Chloro-4,5-dimethylpyridazin-3-amine (CAS-Nr. 76593-36-7, 500 mg,3.17 mmol, 1 .0 eq) and sodium ethanolate in ethanol (16 ml_, 21 w/w-%, 53.9 mmol, 1 7 eq) were heated for 2 h to 130 C in a single mode microwave oven. The reaction mixture was partitioned between DCM and water. The organic phase was washed with brine and dried with sodium sulfate. The resulting mixture was filtered through a Whatman filter and the volatile components were removed in vacuo. The crude mixture was purified via MPLC (Biotage Isolera; 28 g NH2-cartridge: hexane -> hexane/EtOAc 1 /1 ) to give 267 mg (50% yield) of the title compound.UPLC-MS (Method 2): RT = 0.78 min; m/z = 168 (M+H)+.

References: [1]Patent: WO2012/136776,2012,A1 .Location in patent: Page/Page column 117.

16
[ 124-41-4 ]
[ 76593-36-7 ]
[ 1402609-40-8 ]

Yield	Reaction Conditions	Operation in experiment
49%	In methanol; at 30℃; for 1.0h;Microwave irradiation;	6-Chloro-4,5-dimethylpyridazin-3-amine (CAS-Nr. 76593-36-7, 500 mg,3.17 mmol, 1 .0 eq) in 14.51 ml_ of a 25% solution (w/w) of sodium methylate in MeOH was heated for 1 h at 130 C in a single mode microwave oven. The reaction mixture was partitioned between DCM and water. The organic phase was washed with brine and dried (Na2SO4 anh.). Volatile components were removed by the use of a rotary evaporator and the crude mixture was purified via MPLC (Biotage Isolera; 25 g SNAP NH2 cartridge: hexane-> hexane/EtOAc 1 /1 ) to give 250 mg (49% yield) of the title compound.1 H-NMR (400 MHz, d6-DMSO): δ [ppm] = 1 .98 (s, 3H), 2.00 (s, 3H), 5.49 (s, 3H), NH.2 not assigned.

References: [1]Patent: WO2012/136776,2012,A1 .Location in patent: Page/Page column 113-114.

17
[ 76593-36-7 ]
[ 5188-07-8 ]
[ 1402609-42-0 ]