34231-77-1|Methyl pyridazine-4-carboxylate| Ambeed

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Quality Control of [ 34231-77-1 ] Purity: 98% SDS Specification

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Product Details of [ 34231-77-1 ]

CAS No. :	34231-77-1
Formula :	C₆H₆N₂O₂
M.W :	138.12
SMILES Code :	N1=NC=C(C=C1)C(=O)OC
MDL No. :	MFCD09953488
InChI Key :	IJFLWNYKGMQQOW-UHFFFAOYSA-N
Pubchem ID :	12439252

Safety of [ 34231-77-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 34231-77-1 ]

* 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 [ 34231-77-1 ]
Downstream synthetic route of [ 34231-77-1 ]

[ 34231-77-1 ] Synthesis Path-Upstream 1~1

1
[ 75-52-5 ]
[ 50901-42-3 ]
[ 34231-77-1 ]
[ 50901-46-7 ]

References: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1313 - 1321.

[ 34231-77-1 ] Synthesis Path-Downstream 1~36

1
[ 867-89-0 ]
[ 34231-77-1 ]
[ 1202-25-1 ]

References: [1]Justus Liebigs Annalen der Chemie,1973,p. 1955 - 1962.

2
[ 50681-25-9 ]
[ 124-41-4 ]
[ 34231-77-1 ]

References: [1]Arzneimittel-Forschung/Drug Research,1989,vol. 39,p. 1196 - 1201.

3
[ 124-38-9 ]
[ 932-96-7 ]
[ 34231-77-1 ]
[ 132368-98-0 ]
[ 132368-96-8 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1645 - 1647.

4
[ 107125-70-2 ]
[ 34231-77-1 ]
[ 132368-95-7 ]
[ 132368-97-9 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1645 - 1647.
[2]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1645 - 1647.

5
[ 34231-77-1 ]
[ 96054-52-3 ]

References: [1]Liebigs Annalen der Chemie,1985,p. 167 - 182.

6
[ 34231-77-1 ]
2,5-Dihydro-pyridazine-4-carboxylic acid methyl ester [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1989,vol. 39,p. 1196 - 1201.

7
[ 75-52-5 ]
[ 50901-42-3 ]
[ 34231-77-1 ]
[ 50901-46-7 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1313 - 1321.

8
[ 50681-25-9 ]
[ 18107-18-1 ]
[ 34231-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; In dichloromethane; at 0 - 20℃;	Preparation 3: methyl 4-pyridazinecarboxylic acid; To a solution of 4-pyridazinecarboxylic acid (490 mg, 3.9 mmol) in MeOH/DCM (20/10 ml) was added at 0 0C trimethylsilildiazomethane (25.5 mmol). The solution was warm at r.t. and stirred overnight. Volatiles were evaporated in vacuo, the crude dissolved in DCM, washed with NaHCO3 satured and dried over Na2SO4. After filtration and concentration to dryness in vacuo, the crude was purified by column chromatography (DCM:MeOH=98 to2) to give 400 mg of the title compound.NMR (1H, CDCI3): delta 9.65 (s, 1 H)1 9.4 (d, 1 H), 7.98 (d, 1 H)1 4.0 (s, 3H). MS (mlz): 139[MH]+.

References: [1]Patent: WO2006/108701,2006,A1 .Location in patent: Page/Page column 40.

9
[ 34231-77-1 ]
[ 56932-26-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With hydrazine; In tetrahydrofuran; for 4h;Reflux;	Methyl pyridazine-4-carboxylate (0.3g; 2.2mmol) was dissolved in THF (5mL), and 98% hydrazine (0.32mL; 6.4mmol) was added. The mixture was refluxed for 4h, evaporated to dryness and purified by a column chromatography on silica (CHCl3/MeOH 20:1) to give 0.21g (70%) of a yellow amorphous solid. Rf=0.18 (CHCl3/MeOH 10:1). 1H NMR (300MHz, DMSO): delta 10.30 (s, 1H, NH), 9.57-9.48 (m, 1H, Ar), 9.45-9.28 (m, 1H, Ar), 8.00-7.86 (m, 1H, Ar), 4.72 (s, 2H, NH2), in accordance with the literature [65]. 13C NMR (75MHz, DMSO): delta 162.3, 152.3, 148.7, 130.7, 124.1.
	With hydrazine; In methanol; for 12h;Heating / reflux;	Preparation 4: 4-pyridazinecarbo; To a solution of <strong>[34231-77-1]methyl 4-pyridazinecarboxylate</strong> (400 mg, 2.9 mmol) in MeOH (5 ml) was added hydrazine monohydrate (23 mmol). The solution was heated to reflux for 12 h.Volatiles were evaporated in vacuo to give 395 mg of the title compound as a yellow pale foam, which was used without further purification.NMR (1H, DMSO): delta 9.5 (s, 1 H), 9.4 (d, 1 H), 7.98 (d, 1 H), NH and NH2 not observed.MS (zn/z): 139[MH]+.
	With hydrazine hydrate; In methanol;Reflux;	To a solution of <strong>[34231-77-1]methyl pyridazine-4-carboxylate</strong> (0.4 g) in methanol (4.92 ml_) was added hydrazine hydrate (1.16 g) and the mixture was heated at reflux overnight. The reaction mixture was cooled and concentrated to afford pyridazine-4-carbohydrazide as a brown solid. (0715) NMR (400MHz, CDsOD) 9.52-9.48 (m, 1 H) 9.36 (dd, 114) 8.00 (dd, 1 H) (three NH protons missing)

References: [1]European Journal of Medicinal Chemistry,2016,vol. 120,p. 97 - 110.
[2]Chemical Research in Toxicology,2018,vol. 31,p. 435 - 446.
[3]Patent: WO2006/108701,2006,A1 .Location in patent: Page/Page column 40.
[4]Patent: WO2019/185875,2019,A1 .Location in patent: Page/Page column 88-89; 110.

10
[ 67-56-1 ]
[ 50681-25-9 ]
[ 34231-77-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of pyridazine-4-carboxylic acid (Aldrich, 5.0 g, 40.3 mmol) in methanol (anhydrous, Aldrich, 100 mL) was added sulfuric acid (concentrated, Aldrich, 2 mL). The reaction mixture was then heated to reflux and stirred for 16 hours. The volatiles <n="74"/>were removed under reduced pressure. The residue was basified to pH= 8-9 with saturated sodium carbonate (20 mL) and then extracted with EtOAc (3 x 100 mL). The combined extracts were washed with brine (2 x 20 mL) and dried over magnesium sulfate. The drying agent was filtered off and the organic solution was concentrated and dried to give the titled compound. 1H NMR (300 MHz, DMSO-J6) delta 3.34 (s, 3 H), 8.10 (dd, J=5.2, 2.4 Hz, 1 H), 9.52 (dd, J=5.2, 1.2 Hz, 1 H), 9.58 (dd, J=2.2, 1.4 Hz, 1 H) ppm; MS (DCI/NH3) m/z 139 (M+H)+.
	With sulfuric acid; at 70℃; for 14h;	Pyridazine-4-carboxylic acid 0.470 g, 3.79 mmol) was added to an oven dried 15mL pressure flask, followed by anhydrous methanol (10 mL) and concentrated sulfuric acid (0.244 mL, 4.36 mmol). Theflask was sealed and heated at 70 C for 14 h. A sample aliquot was taken from the reaction, dissolved in 1 mL HPLC gradeMeCN, and analyzed with LC-MS to confirm the completion of the reaction. The reaction was diluted with EtOAc (150mL), then washed with half sat. aq. sodium bicarbonate solution (15 mL). The aqueous layer was then re-extracted withEtOAc (50 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and condensed to givethe desired product as an off-white semi-solid (0.262 g, 52%). The crude product was advanced without further purification.This compound has been previously reported and characterized (CAS 34231-77-1). 1H NMR (300 MHz, CDCl3) delta = 3.98(s, 3H), 7.95 (dd, J = 5.1, 2.2 Hz, 1H), 9.40 (d, J = 5.0 Hz, 1H), 9.63 (s, 1H)

References: [1]New Journal of Chemistry,2016,vol. 40,p. 2910 - 2919.
[2]Patent: WO2009/148452,2009,A1 .Location in patent: Page/Page column 72-73.
[3]Physical Chemistry Chemical Physics,2019,vol. 21,p. 7534 - 7543.
[4]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29.

11
[ 6294-89-9 ]
[ 34231-77-1 ]
[ 75-05-8 ]
[ 1232224-92-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 18-crown-6 (0.48 g, 1.8 mM) in tetrahydrofuran (10 mL), there was added a 1.0M potassium tert-butoxide/tetrahydrofuran solution (20 mL, 20 mM) and then the mixture was warmed up to 60 C. Acetonitrile (1.0 mL, 20 mM) was added to the mixture at that temperature, the mixture was stirred for 10 minutes and <strong>[34231-77-1]4-methoxycarbonyl-pyridazine</strong> (2.5 g, 18 mM) was then added thereto. After stirring the mixture at 60 C. for 30 minutes, it was cooled to room temperature, the precipitated solid was recovered through filtration and then washed with tetrahydrofuran. After drying the resulting solid in vacuo, it was suspended in ethanol (50 mL) and then methyl carbazinate (2.3 g, 26 mM) was added thereto. Concentrated hydrochloric acid (1.5 mL) was added to the suspension with ice-cooling and the mixture was stirred at that temperature for 14 hours. The reaction liquid was concentrated under reduced pressure and the excess hydrochloric acid was neutralized by the addition of a saturated sodium bicarbonate aqueous solution. The reaction liquid was extracted with ethyl acetate, the organic phase thus obtained was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to thus give a crude product of the title compound (0.50 g, yield: 13%). MS (ESI) m/z (M+H)+ 220

References: [1]Patent: US2011/294781,2011,A1 .Location in patent: Page/Page column 49; 50.

12
[ 34231-77-1 ]
[ 1232224-95-1 ]

References: [1]Patent: US2011/294781,2011,A1 .

13
[ 34231-77-1 ]
[ 1232224-97-3 ]

References: [1]Patent: US2011/294781,2011,A1 .

14
[ 34231-77-1 ]
C₁₀H₅N₅O₂^(2-)*2Na⁽¹⁺⁾ [ No CAS ]

References: [1]Patent: US2011/294781,2011,A1 .

15
[ 34231-77-1 ]
C₁₄H₁₃ClN₆O [ No CAS ]

References: [1]Patent: US2011/294781,2011,A1 .

16
[ 34231-77-1 ]
[ 1232221-96-3 ]

References: [1]Patent: US2011/294781,2011,A1 .

17
[ 34231-77-1 ]
[ 1232222-02-4 ]

References: [1]Patent: US2011/294781,2011,A1 .

18
[ 34231-77-1 ]
[ 1434271-66-5 ]

References: [1]Patent: WO2013/72265,2013,A1 .
[2]Patent: US2013/123267,2013,A1 .

19
[ 34231-77-1 ]
[ 1434271-67-6 ]

References: [1]Patent: WO2013/72265,2013,A1 .
[2]Patent: US2013/123267,2013,A1 .

20
[ 34231-77-1 ]
[ 1434271-68-7 ]

References: [1]Patent: WO2013/72265,2013,A1 .
[2]Patent: US2013/123267,2013,A1 .

21
[ 34231-77-1 ]
[ 1434271-69-8 ]

References: [1]Patent: WO2013/72265,2013,A1 .
[2]Patent: US2013/123267,2013,A1 .

22
[ 34231-77-1 ]
[ 756-79-6 ]
[ 1434271-65-4 ]

Yield	Reaction Conditions	Operation in experiment
29%	With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -5 - 0℃; for 0.0833333h;	To a solution of <strong>[34231-77-1]methyl pyridazine-4-carboxylate</strong> (1.00 g, 6.95 mmol) and dimethyl methylphosphonate (889 mg, 6.95 mmol) in THF (20 ml) was added a 2 M solution of lithium diisopropylamide (2 M in THF/heptane/ethylbenzene; 7.3 ml, 14.6 mmol) between -5 C and 0 C. Then after 5 min the reaction mixture was carefully quenched with 4 M aq. hydrochloric acid solution to adjust the pH to ca. 6 and diluted with dichloromethane. The aqueous layer was separated and extracted 2 times with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (Si02; gradient ethyl acetate to ethyl acetate/methanol 9: 1) afforded the title compound (460 mg, 29%). Dark red oil; MS: 231.1 [M+H]+.
29%	With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -5 - 0℃; for 0.0833333h;	Step 1: Dimethyl 2-oxo-2-(pyridazin-4-yl)ethylphosphonate To a solution of <strong>[34231-77-1]methylpyridazine-4-carboxylate</strong> (1.00 g, 6.95 mmol) and dimethyl methylphosphonate (889 mg, 6.95 mmol) in THF (20 ml) was added a 2 M solution of lithium diisopropylamide (2 M in THF/heptane/ethylbenzene; 7.3 ml, 14.6 mmol) between -5 C. and 0 C. Then after 5 min the reaction mixture was carefully quenched with 4 M aq. hydrochloric acid solution to adjust the pH to ca. 6 and diluted with dichloromethane. The aqueous layer was separated and extracted 2 times with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; gradient ethyl acetate to ethyl acetate/methanol 9:1) afforded the title compound (460 mg, 29%). Dark red oil; MS: 231.1 [M+H]+.

References: [1]Patent: WO2013/72265,2013,A1 .Location in patent: Page/Page column 52.
[2]Patent: US2013/123267,2013,A1 .Location in patent: Paragraph 0238.

23
[ 34231-77-1 ]
[ 1434271-70-1 ]

References: [1]Patent: WO2013/72265,2013,A1 .

24
[ 34231-77-1 ]
3-(4-piperidin-4-yl-phenyl)-1-pyridazin-4-yl-3-o-tolyl-propan-1-one dihydrochloride [ No CAS ]

References: [1]Patent: WO2013/72265,2013,A1 .

25
bis-(((isopropyl)sulfinyl)oxy)zinc [ No CAS ]
[ 34231-77-1 ]
[ 1448776-98-4 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 12122 - 12134.

26
[ 34231-77-1 ]
(E)-N'-[1-(2-hydroxyphenyl)ethylidene]pyridazine-4-carbohydrazide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2016,vol. 120,p. 97 - 110.

27
[ 7677-24-9 ]
[ 34231-77-1 ]
methyl 3-cyanopyridazine-4-carboxylate [ No CAS ]

References: [1]Chemistry - A European Journal,2017,vol. 23,p. 14733 - 14737.

28
[ 34231-77-1 ]
C₁₃H₁₁N₅O₄ [ No CAS ]

References: [1]Chemical Research in Toxicology,2018,vol. 31,p. 435 - 446.

29
[Re₂(μ-H)(μ-4-OOC-TPA)(CO)₆(μ-(2,5-diphenyl-1,3,4-oxadiazole))] [ No CAS ]
[ 34231-77-1 ]
C₃₁H₂₁N₃O₁₀Re₂ [ No CAS ]

References: [1]Physical Chemistry Chemical Physics,2019,vol. 21,p. 7534 - 7543.

30
C₇₄H₆₈N₄O₁₃Re₂S [ No CAS ]
[ 34231-77-1 ]
C₆₆H₆₄N₄O₁₄Re₂S [ No CAS ]

References: [1]Physical Chemistry Chemical Physics,2019,vol. 21,p. 7534 - 7543.

31
[ 34231-77-1 ]
N-methyl-5-pyridazin-4-yl-1,3,4-thiadiazol-2-amine [ No CAS ]