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[ CAS No. 54709-94-3 ] {[proInfo.proName]}

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Chemical Structure| 54709-94-3
Chemical Structure| 54709-94-3
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Product Details of [ 54709-94-3 ]

CAS No. :54709-94-3 MDL No. :MFCD09743644
Formula : C5H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :MMDFKVYPOQFQHP-UHFFFAOYSA-N
M.W : 110.11 Pubchem ID :327041
Synonyms :

Calculated chemistry of [ 54709-94-3 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.82
TPSA : 45.75 Ų

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) : -7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.05
Log Po/w (XLOGP3) : -0.34
Log Po/w (WLOGP) : 0.08
Log Po/w (MLOGP) : 0.14
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.86
Solubility : 15.1 mg/ml ; 0.137 mol/l
Class : Very soluble
Log S (Ali) : -0.16
Solubility : 76.3 mg/ml ; 0.693 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.88
Solubility : 1.44 mg/ml ; 0.0131 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 54709-94-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54709-94-3 ]

* 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 [ 54709-94-3 ]
  • Downstream synthetic route of [ 54709-94-3 ]

[ 54709-94-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 54709-94-3 ]
  • [ 1120-88-3 ]
Reference: [1] Helvetica Chimica Acta, 1954, vol. 37, p. 1467,1470
  • 2
  • [ 40834-42-2 ]
  • [ 54709-94-3 ]
YieldReaction ConditionsOperation in experiment
80% With hydrazine In tetrahydrofuran at 20 - 60℃; Example 375-Methyl-2H-pyridazin-3-one 5-Hydroxy-4-methyl-5H-furan-2-one (10.0 g, 87.6 mmol) and hydrazine hydrate (4.38 g, 87.6 mmol) were stirred vigorously at room temperature for 1.5 hours in tetrahydrofuran. A solid began to precipitate and the reaction was heated at 60° C. overnight. The crude reaction mixture was concentrated onto silica gel and purified by column chromatography (0 to 10percent methanol in 1:1 EtOAc/dichloromethane) to give 7.7 g (80percent) of the title compound.1H NMR (300 MHz, CDCl3): δ (ppm) 11.38 (broad s, 1H), 7.66 (s, 1H), 6.74 (s, 1H), 2.25 (s, 3H).
80% With hydrazine In tetrahydrofuran at 20 - 60℃; 5-Methyl-2H-pyridazin-3-one γγ°5-Hydroxy-4-methyl-5H-furan-2-one (10.0 g, 87.6 mmol) and hydrazine hydrate (4.38 g, 87.6 mmol) were stirred vigorously at r.t. for 1.5 hours in tetrahydrofuran. A solid began to precipitate and the reaction was heated at 60 °C overnight. The crude reaction mixture was concentrated onto silica gel and purified by column chromatography (0 to 10 percent methanol in 1 :1 EtOAc / dichloromethane) to give 7.7 g (80 percent) of the title compound. 1H NMR (300 MHz, CDCl3) δ 11.38 (br, IH), 7.66 (s, IH), 6.74 (s, IH), 2.25 (s, 3H).
80% With hydrazine In tetrahydrofuran at 20 - 60℃; 5-Methyl-2H-pyridazin-3-one γγ°5-Hydroxy-4-methyl-5H-furan-2-one (10.0 g, 87.6 mmol) and hydrazine hydrate (4.38 g, 87.6 mmol) were stirred vigorously at r.t. for 1.5 hours in tetrahydrofuran. A solid began to precipitate and the reaction was heated at 60 °C overnight. The crude reaction mixture was concentrated onto silica gel and purified by column chromatography (0 to 10 percent methanol in 1 :1 EtOAc / dichloromethane) to give 7.7 g (80 percent) of the title compound. 1H NMR (300 MHz, CDCl3) δ 11.38 (br, IH), 7.66 (s, IH), 6.74 (s, IH), 2.25 (s, 3H).
Reference: [1] Patent: US2007/259860, 2007, A1, . Location in patent: Page/Page column 31
[2] Patent: WO2008/41075, 2008, A1, . Location in patent: Page/Page column 54
[3] Patent: WO2008/41075, 2008, A1, . Location in patent: Page/Page column 54
[4] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4889 - 4894
[5] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4889 - 4894
  • 3
  • [ 83803-81-0 ]
  • [ 54709-94-3 ]
YieldReaction ConditionsOperation in experiment
28%
Stage #1: at 20 - 60℃; for 4 h;
Stage #2: at 60℃; for 5 h;
Example 295-Methyl-2H-pyridazin-3-one The 4,4-dimethoxy-3-methyl-but-2-enoic acid ethyl ester (Qi-Ying Hu, Pankaj D. Rege, and E. J. Corey, J. Am. Chem. Soc., 2004, 126, 5984) (82 g, 440 mmol) was mixed with hydrazine hydrate (50 g, 999 mmol) at room temperature. The mixture was heated at 60° C. for 4 h. After evaporation of solvents the oil residue was further dried under vacuum. To the resulting residue was added 6 M aq. HCl. The mixture was heated at 60° C. for 5 h. The solvents were removed in vacuo. To the residue was added methanol three times, followed by concentration. To the resulting residue was treated with dry ethanol followed by filtration to removed insoluble solid. The filtrate was concentrated to dryness. To the resulting residue was added dry i-PrOH and 20 g anhydrous K2CO3. The mixture was heated for 20 min at 60° C. After filtration, the filtrate was concentrated to dryness. The residue was purified with flash chromatography using DCM:MeOH:Et3N (10:1:0.3) to give the title compound (13.4 g, 28percent).1H NMR (400 MHz, CD3OD): δ (ppm) 2.24 (s, 3H), 6.73 (s, 1H), 7.82 (s, 1H).
28%
Stage #1: at 60℃; for 4 h;
Stage #2: at 60℃; for 5 h;
Stage #3: With potassium carbonate In isopropyl alcohol at 60℃; for 0.333333 h;
Step 14A: 5-Methyl-2H-pyridazin-3-one; The 4,4-dimethoxy-3-methyl-but-2-enoic acid ethyl ester (Qi-Ying Hu, Pankaj D. Rege, and E. J. Corey, J. Am. Chem. Soc., (2004), 126, 5984) (82 g, 440 mmol) was mixed with hydrazine hydrate (50 g, 999 mmol) at room temperature. The mixture was heated at 60° C. for 4 h. After evaporation of solvents the oil residue was further dried under vacuum. To the resulting residue was added 6 M aq. HCl. The mixture was heated at 60° C. for 5 h. The solvents were removed in vacuo. To the residue was added MeOH three times, followed by concentration. The resulting residue was treated with dry EtOH followed by filtration to remove insoluble solids. The filtrate was concentrated to dryness. To the resulting residue was added dry IPA and 20 g anhydrous K2CO3. The mixture was heated for 20 min at 60° C. After filtration, the filtrate was concentrated to dryness. The residue was purified with flash chromatography using DCM:MeOH:TEA (10:1:0.3) to give the subtitle compound (13.4 g, 28percent).1H NMR (400 MHz, CD3OD): d 2.24 (s, 3H), 6.73 (s, 1H), 7.82 (s, 1H).
28%
Stage #1: at 20 - 60℃; for 4 h;
Stage #2: at 60℃; for 5 h;
Stage #3: With potassium carbonate In isopropyl alcohol at 60℃; for 0.333333 h;
Step 10A: 5-Methylpyridazin-3(2H)-one; The 4,4-dimethoxy-3-methyl-but-2-enoic acid ethyl ester (Qi-Ying Au, Pankaj D. Rege, and E. J. Corey, J. Am. Chem. Soc., 2004, 126, 5984) (82 g, 440 mmol) was mixed with hydrazine hydrate (50 g, 999 mmol) at room temperature. The mixture was heated at 60° C. for 4 h. After evaporation of solvents the oil residue was further dried in vacuo. To the resulting residue was added 6 M aq. HCl. The mixture was heated at 60° C. for 5 h. The solvents were removed in vacuo. To the residue was added MeOH three times, followed by concentration in vacuo. The resulting residue was treated with dry EtOH followed by filtration to remove the solids. The filtrate was concentrated in vacuo. To the resulting residue was added dry IPA and 20 g anhydrous K2CO3. The mixture was heated for 20 min at 60° C. After filtration, and removal of solvents in vacuo, the residue was purified with flash chromatography using DCM: MeOH: Et3N (10:1:0.3) to give the subtitle compound (13.4 g, 28percent).1H NMR (400 MHz, MeOH-d4): d 2.24 (s, 3H), 6.73 (s, 1H), 7.82 (s, 1H).
28%
Stage #1: at 20 - 60℃; for 4 h;
Stage #2: at 60℃; for 5 h;
Stage #3: With potassium carbonate In isopropyl alcohol at 60℃; for 0.333333 h;
Step 7A: 5-Methylpyridazin-3(2H)-one The 4,4-dimethoxy-3-methyl-but-2-enoic acid ethyl ester (Qi-Ying Hu, Pankaj D. Rege, and E. J. Corey, J. Am. Chem. Soc., (2004), 126, 5984) (82 g, 440 mmol) was mixed with hydrazine hydrate (50 g, 999 mmol) at room temperature. The mixture was heated at 60° C. for 4 h. After evaporation of solvents the oil residue was further dried under vacuum. To the resulting residue was added 6 M aq. HCl. The mixture was heated at 60° C. for 5 h. The solvents were removed in vacuo. To the residue was added MeOH three times, followed by concentration in vacuo. To the resulting residue was treated with dry ethanol followed by filtration to removed insoluble solid. The filtrate was concentrated to dryness. To the resulting residue was added dry IPA and 20 g anhydrous K2CO3. The mixture was heated to for 20 min at 60° C. After filtration, the filtrate was concentrated to dryness. The residue was purified with flash chromatography using DCM:MeOH:Et3N (10:1:0.3) to give the subtitle compound (13.4 g, 28percent).1H NMR (400 MHz, CD3OD): δ 2.24 (s, 3H), 6.73 (s, 1H), 7.82 (s, 1H).
28%
Stage #1: at 60℃; for 4 h;
Stage #2: With hydrogenchloride In water at 60℃; for 5 h;
Stage #3: With potassium carbonate In isopropyl alcohol at 60℃; for 0.333333 h;
Step 13A:
5-Methylpyridazin-3(2H)-one
The 4,4-dimethoxy-3-methyl-but-2-enoic acid ethyl ester (Qi-Ying Hu, Pankaj D. Rege, and B. J. Corey, J. Am. Chem. Soc., 2004, 126, 5984) (82 g, 440 mmol) was mixed with hydrazine hydrate (50 g, 999 mmol) at room temperature.
The mixture was heated at 60° C. for 4 h.
After evaporation of solvents the oil residue was further dried in vacuo.
To the resulting residue was added 6 M aq. HCl.
The mixture was heated at 60° C. for 5 h.
The solvents were removed in vacuo.
To the residue was added MeOH three times, followed by concentration in vacuo.
The resulting residue was treated with dry EtOH followed by filtration to remove the solids.
The filtrate was concentrated in vacuo.
To the resulting residue was added dry IPA and 20 g anhydrous K2CO3.
The mixture was heated for 20 min at 60° C.
After filtration, and removal of solvents in vacuo, the residue was purified with flash chromatography using DCM:MeOH: Et3N (10:1:0.3) to give the subtitle compound (13.4 g, 28percent).
1H NMR (400 MHz, CD3OD): d 2.24 (s, 3H), 6.73 (s, 1H), 7.82 (s, 1H).

Reference: [1] Patent: US2007/259862, 2007, A1, . Location in patent: Page/Page column 30
[2] Patent: US2009/111820, 2009, A1, . Location in patent: Page/Page column 22
[3] Patent: US2009/111821, 2009, A1, . Location in patent: Page/Page column 23-24
[4] Patent: US2009/111822, 2009, A1, . Location in patent: Page/Page column 10
[5] Patent: US2009/111825, 2009, A1, . Location in patent: Page/Page column 19
  • 4
  • [ 1173165-21-3 ]
  • [ 54709-94-3 ]
Reference: [1] Chemical Communications, 2009, # 21, p. 3008 - 3010
  • 5
  • [ 78920-13-5 ]
  • [ 54709-94-3 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4889 - 4894
  • 6
  • [ 83297-15-8 ]
  • [ 54709-94-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1845 - 1854
  • 7
  • [ 78920-07-7 ]
  • [ 54709-94-3 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4889 - 4894
  • 8
  • [ 19064-64-3 ]
  • [ 54709-94-3 ]
Reference: [1] Yakugaku Zasshi, 1962, vol. 82, p. 304,307[2] Chem.Abstr., 1963, vol. 58, # 3427,
[3] Pharmaceutical Bulletin, 1957, vol. 5, p. 229,233
  • 9
  • [ 1703-07-7 ]
  • [ 54709-94-3 ]
Reference: [1] Pharmaceutical Bulletin, 1957, vol. 5, p. 229,233
[2] Yakugaku Zasshi, 1962, vol. 82, p. 304,307[3] Chem.Abstr., 1963, vol. 58, # 3427,
  • 10
  • [ 89466-36-4 ]
  • [ 54709-94-3 ]
Reference: [1] Yakugaku Zasshi, 1962, vol. 82, p. 304,307[2] Chem.Abstr., 1963, vol. 58, # 3427,
  • 11
  • [ 342402-51-1 ]
  • [ 54709-94-3 ]
Reference: [1] Helvetica Chimica Acta, 1954, vol. 37, p. 1467,1470
  • 12
  • [ 54709-94-3 ]
  • [ 867130-58-3 ]
YieldReaction ConditionsOperation in experiment
87% at 45℃; for 1 h; Example 386-Oxo-1,6-dihydro-pyridazine-4-carboxylic acid The title compound from Example 37 (0.90 g, 8.2 mmol) was stirred in concentrated sulfuric acid (13 mL) and heated to 45° C. Potassium permanganate (3.6 g, 12 mmol) was added portion wise over 30 min to avoid letting the temperature rise. The reaction was allowed to stir for a further 30 min at 45° C. The reaction was then cooled to room temperature and ice was added to the reaction mixture. The resulting precipitate was collected by vacuum filtration, washing with cold water and diethyl ether to give 0.98 g (87percent) of the title compound as the a pale green solid.1H NMR (300 MHz, CDCl3): δ (ppm) 13.39 (broad s, 1H), 8.12 (s, 1H), 7.22 (s, 1H).
87% at 45℃; for 1 h; 6-Oxo-l,6-dihydro-pyridazine-4-carboxylic acidThe title compound from Example 18.2 (0.90 g, 8.17 mmol) was stirred in concentrated sulfuric acid (13 mL) and heated to 45 0C. Potassium permanganate (3.6 g, 12.25 mmol) was added portion wise over 30 min to avoid letting the temperature rise. The reaction was allowed to stir for a further 30 min at 45 0C. The reaction was then cooled to r.t. and ice was added to the reaction mixture. The resulting precipitate was collected by vacuum filtration, washing with cold water and diethyl ether to give 0.978 g (87percent) of the title compound as the a pale green solid. 1H NMR (300 MHz, CDCl3) δ 13.39 (br, IH), 8.12 (s, IH), 7.22 (s, IH).
87% at 45℃; for 1 h; 6-Oxo-l,6-dihydro-pyridazine-4-carboxylic acidThe title compound from Example 18.2 (0.90 g, 8.17 mmol) was stirred in concentrated sulfuric acid (13 mL) and heated to 45 0C. Potassium permanganate (3.6 g, 12.25 mmol) was added portion wise over 30 min to avoid letting the temperature rise. The reaction was allowed to stir for a further 30 min at 45 0C. The reaction was then cooled to r.t. and ice was added to the reaction mixture. The resulting precipitate was collected by vacuum filtration, washing with cold water and diethyl ether to give 0.978 g (87percent) of the title compound as the a pale green solid. 1H NMR (300 MHz, CDCl3) δ 13.39 (br, IH), 8.12 (s, IH), 7.22 (s, IH).
77%
Stage #1: at 50 - 60℃; for 0.5 h;
Stage #2: at 0℃;
Example 306-Oxo-1,6-dihydro-pyridazine-4-carboxylic acid To a stirred solution of the title compound of Example 29 (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60° C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for a further 10 min at 60° C., then the viscous green mixture was poured on crushed ice. The solid powder, which separated, was collected, washed with cold water and dried to give the title compound (4.5 g, 77percent).1H NMR (400 MHz, (CD3)2SO): δ (ppm) 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H).
77% at 50 - 60℃; for 0.5 h; Step 14B: 6-Oxo-1H-pyridazine-4-carboxylic acid; To a stirred solution of the subtitle compound of Step 14A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60° C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for a further 10 min at 60° C., then the viscous green mixture was poured on crushed ice. The solid powder, which separated, was collected, washed with cold water and dried to give the subtitle compound (4.5 g, 77percent).1H NMR (400 MHz, (CD3)2SO): δ 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H).
77% at 50 - 60℃; for 0.5 h; Step 10B: 6-Oxo-1,6-dihydropyridazine-4-carboxylic acid; To a stirred solution of the subtitle compound of Step 10A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60° C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for 10 min at 60° C., the viscous green mixture was poured on crushed ice. The solids were filtered off and washed with cold water. After drying in vacuo the subtitle compound was isolated (4.5 g, 77percent).1H NMR (400 MHz, DMSO-d6): δ 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H).
77% at 50 - 60℃; for 0.5 h; Step 7B: 6-Oxo-1,6-dihydropyridazine-4-carboxylic Acid To a stirred solution of the subtitle compound of Step 7A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60° C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for a further 10 min at 60° C., then the viscous green mixture was poured on crushed ice. The solid powder, which separated, was collected, washed with cold water and dried to give the subtitle compound (4.5 g, 77percent).1H NMR (400 MHz, (CD3)2SO): δ 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H).
77% at 60℃; for 0.166667 h; Step 13B:
6-Oxo-1,6-dihydropyridazine-4-carboxylic acid
To a stirred solution of the subtitle compound of Step 13A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60° C. as a finely ground powder.
The starting material was added to the mixture within 20 min.
Stirring was continued for a further 10 min at 60° C., the viscous green mixture was poured on crushed ice.
The solids were filtered off and washed with cold water.
After drying in vacuo the subtitle compound was isolated (4.5 g, 77percent).
1H NMR (400 MHz, (CD3)2SO): δ 7.22 (s, 3H), 8.13 (s,1H), 13.38 (s, broad, 1H).

Reference: [1] Patent: US2007/259860, 2007, A1, . Location in patent: Page/Page column 31-32
[2] Patent: WO2008/41075, 2008, A1, . Location in patent: Page/Page column 55
[3] Patent: WO2008/41075, 2008, A1, . Location in patent: Page/Page column 55
[4] Patent: US2007/259862, 2007, A1, . Location in patent: Page/Page column 30
[5] Patent: US2009/111820, 2009, A1, . Location in patent: Page/Page column 22
[6] Patent: US2009/111821, 2009, A1, . Location in patent: Page/Page column 24
[7] Patent: US2009/111822, 2009, A1, . Location in patent: Page/Page column 10
[8] Patent: US2009/111825, 2009, A1, . Location in patent: Page/Page column 19
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