[ CAS No. 27372-38-9 ] {[proInfo.proName]}

Name: 27372-38-9|6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid|98%
Brand: Ambeed
SKU: A529081
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2D 3D

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Quality Control of [ 27372-38-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 27372-38-9 ]

SDS Specification

Alternatived Products of [ 27372-38-9 ]

Product Details of [ 27372-38-9 ]

CAS No. :	27372-38-9	MDL No. :	MFCD00052030
Formula :	C₅H₆N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VUADWGRLHPTYPI-UHFFFAOYSA-N
M.W :	142.11	Pubchem ID :	99621
Synonyms :

Calculated chemistry of [ 27372-38-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	39.73
TPSA :	78.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.26
Log Po/w (XLOGP3) :	-1.1
Log Po/w (WLOGP) :	-1.42
Log Po/w (MLOGP) :	-1.04
Log Po/w (SILICOS-IT) :	0.41
Consensus Log Po/w :	-0.58

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	0.04
Solubility :	155.0 mg/ml ; 1.09 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.06
Solubility :	123.0 mg/ml ; 0.864 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.31
Solubility :	69.3 mg/ml ; 0.488 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.62

Safety of [ 27372-38-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 27372-38-9 ]

* 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.

Upstream synthesis route of [ 27372-38-9 ]
Downstream synthetic route of [ 27372-38-9 ]

[ 27372-38-9 ] Synthesis Path-Upstream 1~5

1
[ 27372-38-9 ]
[ 37972-69-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine; copper diacetate; sodium carbonate In toluene at 100℃; for 16 h; Inert atmosphere	6-oxo-1,6-dihydropyridazine-3-carboxylic acid To a solution of 6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid (2.50 g, 17.59 mmol) in toluene (44 mL) was added Cu(OAc)₂ (450 mg, 2.48 mmol), sodium carbonate (7.01 g, 66.14 mmol) and pyridine (4.4 mL) at room temperature. The resulting solution was stirred for 16 h at 100° C. After the reaction was done, the insoluble solids in the reaction mixture were filtered out and the filtrate was concentrated under reduced pressure to yield 6-oxo-1,6-dihydropyridazine-3-carboxylic acid as a off-white solid (1.80 g, 73percent). MS: m/z=177.0 [M+H]⁺.
60%	With bromine; acetic acid In waterReflux	Compound 1a (568 mg, 4.0 mmol)Was placed in a 10 mL double-necked flask,2 mL of acetic acid was added,Magnetic stirring,Heated to boiling,Bromine (0.23 mL, 4.5 mmol) was added dropwise,After the addition, 2 mL of water was added,The mixture was heated to reflux overnight.The reaction was stopped, cooled,A white solid precipitated,Drying by suction filtration 334.1mg.Yield: 60percent;

Reference： [1] European Journal of Organic Chemistry, 2013, # 27, p. 6130 - 6136
[2] Patent: US2016/376283, 2016, A1, . Location in patent: Paragraph 1225; 1226
[3] Patent: CN106187910, 2016, A, . Location in patent: Paragraph 0120; 0121
[4] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 598 - 611

2
[ 27372-38-9 ]
[ 63001-30-9 ]

Reference： [1] Patent: US2016/376283, 2016, A1,

3
[ 27372-38-9 ]
[ 75680-92-1 ]

Reference： [1] Patent: CN106187910, 2016, A,
[2] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 598 - 611

4
[ 27372-38-9 ]
[ 65202-50-8 ]

Reference： [1] Patent: EP3333157, 2018, A1,

5
[ 27372-38-9 ]
[ 56-85-9 ]

Reference： [1] Patent: US2873294, 1958, ,
[2] Patent: US2873294, 1958, ,

[ 27372-38-9 ] Synthesis Path-Downstream 1~88

1
[ 67-56-1 ]
[ 27372-38-9 ]
[ 89532-94-5 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1200,1204, 1206

3
[ 27372-38-9 ]
[ 61468-81-3 ]

Yield	Reaction Conditions	Operation in experiment
1.19 g	at 220℃; for 0.416667h;	Reference Example 6-1-B 2,3,4,5-Tetrahydropyridazin-3-one Reference Example 6-1-A (2.00 g) was heated at 220C for 25 minutes. The reaction mixture was allowed to cool to room temperature to give the title compound (1.19 g).

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 60
[2]European Journal of Medicinal Chemistry,2013,vol. 64,p. 512 - 528
[3]Patent: EP3459941,2019,A1 .Location in patent: Paragraph 0455

4
[ 27372-38-9 ]
[ 56-85-9 ]

Reference： [1]Patent: US2873294,1958,

5
[ 328-50-7 ]
[ 27372-38-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With carbazic acid; at 90℃; for 3.0h;Green chemistry;	General procedure: A 10.0 mmol for alpha-keto acid compound or a 5.2 mmol for beta-diketones or alpha-keto acids was mixed with 0.40 g of hydrazinium carboxylate (1a, 5.2 mmol), respectively. (For solid di-carbonyl compound, the mixture was ground using a pestle and a mortar.) The mixture was stored in a closed vial, and then heated to 70 - 90 C until the reaction was complete. Complete conversion to related product was dependent upon the nature of di-carbonyl compounds. Typically, those di-carbonyl compounds take about <3 h to complete the reactions. CO2 and water were released during the reaction. All products obtained from the reactions of 1a with di-carbonyl compounds were basically characterized by 1H and 13C NMR spectroscopy. The products have over 97% of purity of reaction mixture based on 1H NMR spectroscopy and isolation yields are over 97% based on di-carbonyl compounds. The melting points, elemental analysis and UV-Vis spectra for all azines, pyrazoles and pyridazinones, were measured after purification using appropriate solvent.
62%	With sodium hydroxide; hydrazinium sulfate; In water;	Sodium hydroxide (0.69 g, 17.25 mmol)And hydrazine sulfate (1.02 g, 7.85 mmol)Was placed in a 10 mL double-necked flask,4.5 mL of hot water was added to dissolve,Magnetic stirring slowly dropping1.8 mL of a hot aqueous solution of alpha-ketoglutaric acid (1.14 g, 7.81 mmol)After completion of the dropwise addition, the reaction solution was heated to slightly boil,The reaction was over night.The reaction was stopped,Cooling under ice bath standing white solid precipitation,Filtration.The white solid obtained by suction filtration was recrystallized from 2N hydrochloric acid to give 691.1 mg of colorless needles.Yield: 62%;
62.3%	With sodium hydroxide; hydrazinium sulfate; In water; at 105℃;	A well-stirred solution of alpha-ketoglutaric acid (1.14 g, 7.81 mmol) in hot water (1.8 mL) was added slowly, with stirring to a solution of sodium hydroxide (0.69 g, 17.25 mmol) and hydrazinium sulfate (1.02 g, 7.85 mmol) in hot water (4.5 mL). The mixture was heated to moderate boiling overnight, and then refrigerated in ice bath for several hours. The precipitate was collected by filtration and recrystallized with 2 N HCl to provide 11 as a colorless needle crystal (691.1 mg, yield 62.3%). Mp: 195.4-195.9 C (Ref. melting point 195-196 C [55]).

	With hydrazine hydrate; In ethanol; at 60℃;	General procedure: To a stirred solution of the suitable gamma-keto acid 1a-k (1.00 mmol) in EtOH (2 mL), hydrazine hydrate (1.00 mmol) was added dropwise. The mixture was heated at 60 C for 1-3h. After cooling, the precipitate was collected by suction and purified by recrystallization from either toluene or ethanol.
	With hydrazine hydrate; In ethanol; at 60℃; for 2.0h;	Hydrazine hydrate (1.2 mL) was slowly added to [alpha] -ketoglutaric acid (0.014 mol, 2.00 g)In an ethanol solution at a constant temperature of 60 C for 2 h. After the reaction, decompression,The residue was washed with ethanol to give a white powder.
2.04 g	With hydrazine hydrate; In ethanol; at 60℃; for 2.0h;	To a solution of 2-oxoglutaric acid (2.00 g) in ethanol (10 mL) was added hydrazine monohydrate (ca. 80%, 1.20 mL), and the mixture was stirred at 60C for 2 hours. The reaction mixture was allowed to cool to room temperature, and then the reaction mixture was cooled with ice. The precipitated solid was collected by filtration. The obtained solid was washed with diethyl ether to give the title compound(2.04 g).

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1384 - 1388
[2]Journal of Physical Organic Chemistry,2000,vol. 13,p. 388 - 394
[3]Patent: CN106187910,2016,A .Location in patent: Paragraph 0118; 0119
[4]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611
[5]Bulletin de la Societe Chimique de France,1911,vol. <4> 9,p. 463
[6]Chemische Berichte,1909,vol. 42,p. 657
[7]Journal fur praktische Chemie (Leipzig 1954),1927,vol. <2> 116,p. 156,158
[8]European Journal of Medicinal Chemistry,2013,vol. 64,p. 512 - 528
[9]Patent: CN105017197,2017,B .Location in patent: Paragraph 0179; 0184; 0186
[10]Patent: EP3459941,2019,A1 .Location in patent: Paragraph 0454

6
[ 27372-38-9 ]
[ 156500-89-9 ]
6-Oxo-1,4,5,6-tetrahydro-pyridazine-3-carboxylic acid [4,5-bis-(4-methoxy-phenyl)-thiazol-2-ylmethyl]-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1189 - 1199

7
[ 27372-38-9 ]
3-(1-amino-1,1-dimethylmethyl)-5,6-bis(4-methoxyphenyl)-1,2,4-triazine hydrochloride [ No CAS ]
6-Oxo-1,4,5,6-tetrahydro-pyridazine-3-carboxylic acid {1-[5,6-bis-(4-methoxy-phenyl)-[1,2,4]triazin-3-yl]-1-methyl-ethyl}-amide [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1835 - 1840

8
[ 27372-38-9 ]
[ 141424-55-7 ]
6-<N-<5,6-bis(4-methoxyphenyl)-1,2,4-triazin-3-yl>methyl>carbamoyl-2,3,4,5-tetrahydro-3-pyridazinone [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1835 - 1840

Yield	Reaction Conditions	Operation in experiment
99%	With carbazic acid; In neat (no solvent); at 90℃; for 1.5h;	General procedure: 2-oxo-pentanoic acid was used 5.82 g of 1.5 hours at 90C, the rest is the same as in Example 1. The obtained compound was 6-methyl-4,5-dihydropyridazin-3 (2H) -one, the selectivity was> 99%, and the yield was 98%.
		Analogously, by hydrolysis of the methyl 2-(1, 3-benzodioxol-5-yl)-2-(T-yl)acetates below, in which T is 6-phenyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-chlorophenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-ethoxycarbonylphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-methoxycarbonyl-2,3,4,5-tetrahydropyridazine-3-on-2 6-(2,5-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(thien-2-yl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(furan-2-yl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-phenyl-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-methoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-chlorophenyl)-4-methyl-2,3,4,5,-tetrahydropyridazin-3-on-2 6-(4-ethoxycarbonylphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(2,5-dimethoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(thien-2-yl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(furan-2-yl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 4,4,6-trimethyl-2,3,4,5-tetrahydropyridazin-3-on-2 4,6-dimethyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-phenyl-2,3-dihydropyridazin-3-on-2 5-phenyl-6-methyl-2,3-dihydropyridazin-3-one-2 4-phenyl-6-methyl-2,3-dihydropyridazin-3-one-2 6-(4-methoxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(4-chlorophenyl)-2,3-dihydropyridazin-3-on-2 6-(4-methoxycarbonylphenyl)-2,3-dihydropyridazin-3-on-2 6-(2,5-dimethoxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(thien-2-yl)-2,3-dihydropyridazin-3-on-2 6-(furan-2-yl)-2,3-dihydropyridazin-3-on-2 6-phenyl-4-methyl-2,3-dihydropyridazin-3-on-2 6-(4-methoxyphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(4-chlorophenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(4-chlorophenyl)-5-methyl-2,3-dihydropyridazin-3-on-2 6-(4-ethoxycarbonylphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(2,5-dimethoxyphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(thien-2-yl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(furan-2-yl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-methyl-2,3-dihydropyridazin-3-on-2 6-propyl-2,3-dihydropyridazin-3-one-2 4-propyl-6-methyl-2,3-dihydropyridazin-3-on-2 4-ethyl-6-methyl-2,3-dihydropyridazin-3-one-2 4-methyl-6-ethyl-2,3-dihydropyridazin-3-one-2 4-methyl-6-propyl-2,3-dihydropyridazin-3-on-2 5,6-dimethyl-2,3-dihydropyridazin-3-on-2 4,5,6-trimethyl-2,3-dihydropyridazin-3-on-2 4-methyl-2,3-dihydropyridazin-3-on-2 5-(4-methoxyphenyl)-2H-3,6-dihydro-1,3,4-thiadiazin-2-on-3 5-(3,4-dimethoxyphenyl)-6-ethyl-2H-3,6-dihydro-1,3,4-thiadiazin-2-on-3 6-(4-methanesulfonylphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 2,3-dihydropyridazin-3-one-2 4-(4-methoxybenzyl)-6-methyl-2,3-dihydropyridazin-3-one-2 6-tert.-butyl-2,3-dihydropyridazin-3-one-2 6-cyclopropyl-2,3-dihydropyridazin-3-one-2, the 2-(1,3-benzodioxol-5-yl)-2-(T-yl)acetic acids below are obtained, in which T is 6-phenyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2, m.p. 181 6-(4-chlorophenyl)-2,3,4,5-tetrahydropyridazin-3-on-2, m.p. 168 6-(4-carboxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2, m.p. 184 6-carboxy-2,3,4,5-tetrahydropyridazine-3-one, m.p. 178 6-(2,5-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2, m.p. 149

11
[ 27372-38-9 ]
[ 7732-18-5 ]
palladium/BaSO₄ [ No CAS ]
[ 56-85-9 ]

Reference： [1]Patent: US2873294,1958,

12
[ 27372-38-9 ]
[ 7732-18-5 ]
palladium/charcoal [ No CAS ]
[ 56-85-9 ]

Reference： [1]Patent: US2873294,1958,

13
[ 27372-38-9 ]
[ 98142-90-6 ]

Reference： [1]Yakugaku Kenkyu,1956,vol. 28,p. 609,611, 612
Chem.Abstr.,1957,p. 16483

14
[ 27372-38-9 ]
[ 300-22-1 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1200,1204, 1206

15
[ 27372-38-9 ]
[ 33548-32-2 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1200,1204, 1206

16
[ 27372-38-9 ]
[ 99419-11-1 ]

Reference： [1]Yakugaku Kenkyu,1956,vol. 28,p. 609,611, 612
Chem.Abstr.,1957,p. 16483
[2]Patent: CN105017197,2017,B

17
[ 27372-38-9 ]
[ 90110-44-4 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1200,1204, 1206

18
[ 27372-38-9 ]
[ 90768-80-2 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1200,1204, 1206

19
[ 27372-38-9 ]
[ 114536-01-5 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1200,1204, 1206

20
[ 27372-38-9 ]
[ 99167-77-8 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1200,1204, 1206

21
[ 42126-21-6 ]
[ 27372-38-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1911,vol. <4> 9,p. 463

Yield	Reaction Conditions	Operation in experiment
		Analogously, by reaction of 4-isopropylbenzenesulfonamide with the 2-(1,3-benzodioxol-5-yl)-2-(T-yl)acetic acids below, in which T is 6-phenyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-chlorophenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-carboxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-carboxy-2,3,4,5-tetrahydropyridazine-3-on-2 6-(2,5-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-one 6-(thien-2-yl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-(furan-2-yl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-phenyl-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-methoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-chlorophenyl)-4-methyl-2,3,4,5,-tetrahydropyridazin-3-on-2 6-(4-carboxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(2,5-dimethoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(thien-2-yl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(furan-2-yl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 4,4,6-trimethyl-2,3,4,5-tetrahydropyridazin-3-on-2 4,6-dimethyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-phenyl-2,3-dihydropyridazin-3-on-2 5-phenyl-6-methyl-2,3-dihydropyridazin-3-one-2 6-(4-methoxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(4-chlorophenyl)-2,3-dihydropyridazin-3-on-2 6-(4-carbonylphenyl)-2,3-dihydropyridazin-3-on-2 6-(2,5-dimethoxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(thien-2-y) -2,3-dihydropyridazin-3-on-2 6-(furan-2-yl)-2,3-dihydropyridazin-3-on-2 6-phenyl-4-methyl-2,3-dihydropyridazin-3-on-2 6-(4-methoxyphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(4-chlorophenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(4-chlorophenyl)-5-methyl-2,3-dihydropyridazin-3-on-2 6-(4-carboxylphenyl)-4-methyl-2,3-dihydropyridazin-3 -on-2 6-(2,5-dimethoxyphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(thien-2-yl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(furan-2-yl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-methyl-2,3-dihydropyridazin-3-on-2 6-propyl-2,3-dihydropyridazin-3-one-2 4-propyl-6-methyl-2,3-dihydropyridazin-3-on-2 4-ethyl-6-methyl-2,3-dihydropyridazin-3-one-2 4-methyl-6-propyl-2,3-dihydropyridazin-3-on-2 5,6-dimethyl-2,3-dihydropyridazin-3-on-2 4,5,6-trimethyl-2,3-dihydropyridazin-3-on-2 4-methyl-2,3-dihydropyridazin-3-on-2 5-(4-methoxyphenyl)-2H-3,6-dihydro-1,3,4-thiadiazin-2-on-3 5-(3,4-dimethoxyphenyl)-6-ethyl-2H-3,6-dihydro-1,3,4-thiadiazin-2-on-3 4,6-dimethyl-2,3-dihydropyridazin-3-one-2 4-(4-methoxybenzyl)-6-methyl-2,3-dihydropyridazin-3-one-2 6-tert.-butyl-2,3-dihydropyridazin-3-one-2 6-cyclopropyl-2,3-dihydropyridazin-3-one-2, the following 2-(1,3-benzodioxol-5-yl)-2-(T-yl)N-(4-isopropylphenylsulfonyl)acetamides are obtained, in which T is 6-phenyl-2,3,4,5-tetrahydropyridazin-3-on-2, m.p. 187 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2, FAB 564 6-(4-chlorophenyl)-2,3,4,5-tetrahydropyridazin-3-on-2, FAB 568 6-(4-carboxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-carboxy-2,3,4,5-tetrahydropyridazine-3-one 6-(2,5-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2, m.p. 187 6-(3,4-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-on-2, m.p. 223 6-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-one, FAB 594 6-(thien-2-yl)-2,3,4,5-tetrahydropyridazin-3-on-2, m.p. 190 6-(furan-2-yl)-2,3,4,5-tetrahydropyridazin-3-on-2 6-phenyl-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-methoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(4-chlorophenyl)-4-methyl-2,3,4,5,-tetrahydropyridazin-3-on-2 6-(4-carboxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(2,5-dimethoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(thien-2-yl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-(furan-2-yl)-4-methyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-methyl-2,3,4,5-tetrahydropyridazin-3-on-2, FAB 470 4,4,6-trimethyl-2,3,4,5-tetrahydropyridazin-3-on-2 4,6-dimethyl-2,3,4,5-tetrahydropyridazin-3-on-2 6-phenyl-2,3-dihydropyridazin-3-on-2 5-phenyl-6-methyl-2,3-dihydropyridazin-3-one-2 6-(4-methoxyphenyl)-2,3-dihydropyridazin-3-on-2, m.p. 164 6-(4-chlorophenyl)-2,3-dihydropyridazin-3-on-2 6-(4-carboxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(2,5-dimethoxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(3,4-dimethoxyphenyl)-2,3-dihydropyridazin-3-on-2 6-(thien-2-yl)-2,3-dihydropyridazin-3-on-2 6-(furan-2-yl)-2,3-dihydropyridazin-3-on-2 6-phenyl-4-methyl-2,3-dihydropyridazin-3-on-2, m.p. 196 6-(4-methoxyphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2, FAB 579 6-(4-chlorophenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(4-chlorophenyl)-5-methyl-2,3-dihydropyridazin-3-on-2 6-(4-carboxyphenyl)-4-methyl-2,3-dihydropyridazin-3-on-2 6-(2,5-dimethoxyphenyl)-4-methyl-2,3-dihydro...

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[ 37972-69-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine; copper diacetate; sodium carbonate; In toluene; at 100℃; for 16h;Inert atmosphere;	6-oxo-1,6-dihydropyridazine-3-carboxylic acid To a solution of 6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid (2.50 g, 17.59 mmol) in toluene (44 mL) was added Cu(OAc)2 (450 mg, 2.48 mmol), sodium carbonate (7.01 g, 66.14 mmol) and pyridine (4.4 mL) at room temperature. The resulting solution was stirred for 16 h at 100 C. After the reaction was done, the insoluble solids in the reaction mixture were filtered out and the filtrate was concentrated under reduced pressure to yield 6-oxo-1,6-dihydropyridazine-3-carboxylic acid as a off-white solid (1.80 g, 73%). MS: m/z=177.0 [M+H]+.
60%	With bromine; acetic acid; In water;Reflux;	Compound 1a (568 mg, 4.0 mmol)Was placed in a 10 mL double-necked flask,2 mL of acetic acid was added,Magnetic stirring,Heated to boiling,Bromine (0.23 mL, 4.5 mmol) was added dropwise,After the addition, 2 mL of water was added,The mixture was heated to reflux overnight.The reaction was stopped, cooled,A white solid precipitated,Drying by suction filtration 334.1mg.Yield: 60%;
	With bromine; acetic acid; In water;Reflux;	To a solution of 11 (568 mg, 4.00 mmol) in glacial acetic acid (2.0 mL) was vigorously stirred at slight boiling temperature, then bromine (230 muL, 4.50 mmol) was added via dropping funnel. When all of the bromine had been introduced, water (2.0 mL) was added and the reaction mixture was heated under reflux temperature overnight. After cooling to room temperature, the precipitate was filtrated, and then dried to give crude product 12 without further purification. The average yield of acid which precipitated was 334.1 mg (60.0%). Mp: 258.4-258.6 C (Ref. melting point 257 C [55]).

Reference： [1]European Journal of Organic Chemistry,2013,p. 6130 - 6136
[2]Patent: US2016/376283,2016,A1 .Location in patent: Paragraph 1225; 1226
[3]Patent: CN106187910,2016,A .Location in patent: Paragraph 0120; 0121
[4]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

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[ 6531-04-0 ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

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6-chloro-N-cyclohexylpyridazine-3-carboxamide [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

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N-cyclohexyl-6-morpholinopyridazine-3-carboxamide [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

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N-benzyl-6-chloropyridazine-3-carboxamide [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A

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N-benzyl-6-morpholinopyridazine-3-carboxamide [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A

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N-benzyl-6-(cyclohexylamino)pyridazine-3-carboxamide [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A

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[ 27372-38-9 ]
[ 63001-31-0 ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

31
[ 27372-38-9 ]
[ 75680-92-1 ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

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[ 27372-38-9 ]
6-chloro-4-isopropylpyridazine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

33
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6-chloro-5-isopropylpyridazine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

34
[ 27372-38-9 ]
6-chloro-5-isopropylpyridazine-3-carbonyl chloride [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

35
[ 27372-38-9 ]
6-chloro-4-isopropylpyridazine-3-carbonyl chloride [ No CAS ]

Reference： [1]Patent: CN106187910,2016,A
[2]European Journal of Medicinal Chemistry,2017,vol. 137,p. 598 - 611

36
[ 27372-38-9 ]
[ 63001-30-9 ]

Reference： [1]Patent: US2016/376283,2016,A1

37
[ 27372-38-9 ]
[ 1591827-38-1 ]

Reference： [1]Patent: US2016/376283,2016,A1

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methyl 6-(benzyloxy)-5-bromopyridazine-3-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/376283,2016,A1

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N-cyclohexyl-6-chloro-4-isopropylpyridazine-3-carboxamide [ No CAS ]