307307-84-2|Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate| Ambeed

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Quality Control of [ 307307-84-2 ] Purity: 95% SDS Specification

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Product Details of [ 307307-84-2 ]

CAS No. :	307307-84-2
Formula :	C₁₀H₁₄N₂O₂
M.W :	194.23
SMILES Code :	O=C(C1=NN2CCCCC2=C1)OCC
MDL No. :	MFCD11975790
InChI Key :	RLYRMESNENRMHE-UHFFFAOYSA-N
Pubchem ID :	11845784

Safety of [ 307307-84-2 ]

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

Application In Synthesis of [ 307307-84-2 ]

* 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 [ 307307-84-2 ]

[ 307307-84-2 ] Synthesis Path-Downstream 1~27

1
[ 307307-84-2 ]
[ 623564-49-8 ]

Yield	Reaction Conditions	Operation in experiment
95%		Step 3: (4. 5, 6, 7-Tetrahvdropyrazolof1. 5-alpyridin-2-vl) methanol; MeOH (0.29 mL) was added to the THF (19 mL) solution of LiBH4 (cont. 90%) (174 mg) under a nitrogen atmosphere at room temperature, then 4,5, 6,7- tetrahydropyrazolo [1,5-a] pyridine-2-carboxylic acid ethyl ester (862 mg) was added to the suspension and stirred for 1 h at room temperature and 1.5 h at 40 C. The mixture was quenched with 1 mol/L HCI at pH 1 and stirred for 1 h at room temperature. Solid K2CO3 was added to the solution to adjust pH to 8 and the mixture was extracted with AcOEt. The organic layer was dried (MgS04) and filtered. The filtrate was concentrated under reduced pressure to afford titled compound as pale yellow oil (691 mg, 95%). 1H NMR (CDCI3) 8 1. 80-1.87 (m, 2H), 1.98-2. 05 (m, 2H), 2.77 (t, 2H, J = 6.4 Hz), 2.81-2. 84 (br, 1H), 4.09 (t, 2H, J = 6.1 Hz), 4.62 (d, 2H, J = 5.3 Hz), 5.96 (s, 1H).
95%	With hydrogenchloride; lithium borohydride; potassium carbonate; In tetrahydrofuran; methanol;	Step 3 (4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridin-2-yl)methanol MeOH (0.29 mL) was added to the THF (19 mL) solution of LiBH4 (cont. 90%) (174 mg) under a nitrogen atmosphere at room temperature, then <strong>[307307-84-2]4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester</strong> (862 mg) was added to the suspension and stirred for 1 h at room temperature and 1.5 h at 40 C. The mixture was quenched with 1 mol/L HCl at pH 1 and stirred for 1 h at room temperature. Solid K2CO3 was added to the solution to adjust pH to 8 and the mixture was extracted with AcOEt. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to afford titled compound as pale yellow oil (691 mg, 95%). 1H NMR (CDCl3) delta 1.80-1.87 (m, 2H), 1.98-2.05 (m, 2H), 2.77 (t, 2H, J=6.4 Hz), 2.81-2.84 (br, 1H), 4.09 (t, 2H, J=6.1 Hz), 4.62 (d, 2H, J=5.3 Hz), 5.96 (s, 1H).
95%		Step 3: (4, 5, 6, 7-Tetrahvdropvrazolof1, 5-alpyridin-2-vl) methanol MeOH (0.29 mL) was added to the THF (19 mL) solution of LiBH4 (cont. 90%) (174 mg) under a nitrogen atmosphere at room temperature, then 4,5, 6,7- tetrahydropyrazolo [1,5-a] pyridine-2-carboxylic acid ethyl ester (862 mg) was added to the suspension and stirred for 1 h at room temperature and 1.5 h at 40 C. The mixture was quenched with 1 mol/L HCI at pH 1 and stirred for 1 h at room temperature. Solid K2CO3 was added to the solution to adjust pH to 8 and the mixture was extracted with AcOEt. The organic layer was dried (MgS04) and filtered. The filtrate was concentrated under reduced pressure to afford titled compound as pale yellow oil (691 mg, 95%). 'H NMR (CDCI3) 8 1. 80-1.87 (m, 2H), 1.98-2. 05 (m, 2H), 2.77 (t, 2H, J = 6.4 Hz), 2.81-2. 84 (br, 1H), 4.09 (t, 2H, J= 6.1 Hz), 4.62 (d, 2H, J= 5.3 Hz), 5.96 (s, 1H).

95%

MeOH (0.29 mL) was added to the THF. (19 mL) solution of LiBH4 (cont. 90%) (174 mg) under a nitrogen atmosphere at room temperature, then <strong>[307307-84-2]4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester</strong> (862 mg) was added to the suspension and stirred for 1 h at room temperature and 1.5 h at 40 C. The mixture was quenched with 1 mol/L HCl at pH 1 and stirred for 1 h at room temperature. Solid K2CO3 was added to the solution to adjust pH to 8 and the mixture was extracted with AcOEt. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to afford titled compound as pale yellow oil (691 mg, 95%). 1H NMR (CDCl3) delta1.80-1.87 (m, 2H), 1.98-2.05 (m, 2H), 2.77 (t, 2H, J=6.4 Hz), 2.81-2.84 (br, 1H), 4.09 (t, 2H, J=6.1 Hz), 4.62 (d, 2H, J=5.3 Hz), 5.96 (s, 1H).

References: [1]Patent: WO2003/93279,2003,A1 .Location in patent: Page/Page column 70.
[2]Patent: US2004/132708,2004,A1 .
[3]Patent: WO2003/93277,2003,A1 .Location in patent: Page/Page column 98.
[4]Patent: US2006/276445,2006,A1 .Location in patent: Page/Page column 19.
[5]Journal of Medicinal Chemistry,2006,vol. 49,p. 4623 - 4637.

2
[ 105786-95-6 ]
[ 623-47-2 ]
[ 307307-84-2 ]
[ 118055-06-4 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4623 - 4637.
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.

3
[ 307307-84-2 ]
[ 307313-06-0 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4623 - 4637.

4
[ 307307-84-2 ]
[ 1025959-41-4 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4623 - 4637.

5
[ 307307-84-2 ]
(5R),(6Z)-7-oxo-6-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-ylmethylene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4623 - 4637.

6
[ 4515-18-8 ]
[ 307307-84-2 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4623 - 4637.
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.
[3]Patent: CN108948019,2018,A .

7
[ 4043-87-2 ]
[ 307307-84-2 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4623 - 4637.
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.
[3]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.
[4]Patent: CN108948019,2018,A .

8
[ 105786-95-6 ]
[ 623-47-2 ]
[ 307307-84-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	In xylene; for 6h;Reflux;	Ethyl propiolate (2.4 ml_, 23.7 mmol) was slowly added to a solution of reference example 14 (2.99 g, 21.3 mmol) in xylene (mixture of isomers, 40 ml_). The mixture was heated to reflux for 6 hours and the solvent was distilled off. The residue was purified by chromatography over silica gel using hexane/EtOAc mixtures of increasing polarity as eluent, to afford 2.3 g of the desired compound (yield: 56%). LC-MS (Method 2): tR = 1.63 min; m/z = 195 (MH+).
40.4%	In 5,5-dimethyl-1,3-cyclohexadiene; at 125℃; for 12h;	4,5,6,7-tetrahydro-3-oxo-[1,2,3]oxadiazolo[3,4-a]pyridin-8-indole (17.00 g, 121.3 mmol), Xylene (80 mL) and ethyl propiolate (18.7 mL, 185 mmol) were placed in a 250 mL round bottom flask, and reacted under nitrogen for 12 h at 125 C. The reaction was complete by TLC. The mixture was spin-dried, and subjected to silica gel column chromatography, gradient elution of PE:EA=20:1-2:1 to obtain 9.52 g of a yellow liquid, the yield was 40.4%.
32%	In 5,5-dimethyl-1,3-cyclohexadiene; for 2h;Reflux;	General procedure: A mixture of 22a (13.0 g, 93 mmol), and ethyl propiolate (28.5 mL, 278 mmol), in xylene (250 mL) was heated under reflux for 2 h. The cooled mixture was evaporated under reduced pressure. The residual oil was purified by column chromatography (diethylether), to afford the title compound as an oil, (5.82 g, 32%). 1H NMR (CDCl3) delta: 1.39 (t, 3H), 1.88 (m, 2H), 2.06 (m, 2H), 2.82 (t, 2H), 4.20 (t, 2H), 4.39 (q, 2H), 6.55 (s, 1H). LRMS (Thermospray) m/z: 195.2 (M+1)+.

26%

In o-xylene; for 16h;Heating / reflux;

Step 2: 4, 5, 6, 7-TetrahYdropYrazolof1 5-alpvridine-2-carboxvlic acid ethylester :; Ethyl propiolate (804 mg) was added to the o-xylene (15 mL) solution of tetrahydropyridino [1,2-c] [1, 2,3] oxadiazolone (1.04 g) under a nitrogen atmosphere and refluxed for 16 h. The solution was concentrated under a reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane-AcOEt (2/1-1/1). The titled compound was obtained as yellow oil (871 mg, 65%), and 4,5, 6, 7-tetrahydropyrazolo [1,5-a] pyridine-3-carboxylic acid ethyl ester was obtained as yellow oil (345 mg, 26%). 'H NMR (CDCI3) 61. 39 (t, 3H, J = 7.1 Hz), 1.84-1. 91 (m, 2H), 2.02-2. 09 (m, 2H), 2.82 (t, 2H, J = 6.4 Hz), 4.22 (t, 2H, J = 6.2 Hz), 4.39 (q, 2H, J = 7.1 Hz), 6.53 (s, 1 H).

References: [1]Patent: WO2010/43633,2010,A1 .Location in patent: Page/Page column 101-102.
[2]Patent: CN108948019,2018,A .Location in patent: Paragraph 0404; 0413; 0414.
[3]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.
[4]Patent: WO2003/93279,2003,A1 .Location in patent: Page/Page column 69-70.
[5]Patent: EP1241170,2002,A2 .Location in patent: Page 47.

9
[ 307307-84-2 ]
[ 307313-03-7 ]

Yield	Reaction Conditions	Operation in experiment
84.8%	With water; sodium hydroxide; at 0 - 20℃; for 3.5h;	Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate (7.69 g, 39.6 mmol), H2O (60 mL)Add 250 mL round bottom flask, cool to 0 C, then add sodium hydroxide (7.90 g, 198 mmol) and continue to stir for 30 min.The reaction was further carried out for 3 h at room temperature, and the reaction of the starting material was completely confirmed by TLC.Add DCM (60 mL) to extract the liquid, and adjust the pH to 5 with concentrated hydrochloric acid.After standing, a yellow-white solid precipitated and was filtered.The yellow solid was 5.58g, and the yield was 84.8%.
		General procedure: (i) Sodium hydroxide solution (20 mL, 2 M, 40 mmol) was added to a solution of 23a (5.8 g, 30 mmol) in dioxan (100 mL), and the reaction stirred at room temperature for 18 h. The mixture was evaporated under reduced pressure and HCl (2 M, 21 mL) was added. The mixture was evaporated under reduced pressure, the residue azeotroped with toluene, and the product dried under vacuum.

References: [1]Patent: CN108948019,2018,A .Location in patent: Paragraph 0404; 0415; 0416.
[2]Patent: EP1241170,2002,A2 .Location in patent: Page 59.
[3]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.
[4]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.

10
[ 121193-65-5 ]
[ 623-47-2 ]
[ 307307-84-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	In o-xylene; for 16h;Heating / reflux;	Step 2: 4, 5, 6, 7-Tetrahvdropvrazolof1, 5-alpvridine-2-carboxylic ; acid ethvlester : Ethyl propiolate (804 mg) was added to the o-xylene (15 mL) solution of tetrahydropyridino [1, 2-c] [1,2, 3] oxadiazolone (1.04 g) under a nitrogen atmosphere and refluxed for 16 h. The solution was concentrated under a reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane-AcOEt (2/1-1/1). The titled compound was obtained as yellow oil (871 mg, 65%), and 4,5, 6, 7-tetrahydropyrazolo [1,5-a] pyridine-3-carboxylic acid ethyl ester was obtained as yellow oil (345 mg, 26%). 'H NMR (CDCI3) 8 1. 39 (t, 3H, J = 7.1 Hz), 1.84-1. 91 (m, 2H), 2.02-2. 09 (m, 2H), 2.82 (t, 2H, J = 6.4 Hz), 4.22 (t, 2H, J = 6.2 Hz), 4.39 (q, 2H, J = 7.1 Hz), 6.53 (s, 1H).

References: [1]Patent: WO2003/93277,2003,A1 .Location in patent: Page/Page column 98.

11
[ 121193-65-5 ]
[ 623-47-2 ]
[ 307307-84-2 ]
[ 118055-06-4 ]

Yield	Reaction Conditions	Operation in experiment
65%; 26%	In o-xylene; for 16h;Heating / reflux;	Ethyl propiolate (804 mg) was added to the oxylene (15 mL) solution of tetrahydropyridino[1,2-c][1,2,3]oxadiazolone (1.04 g) under a nitrogen atmosphere and refluxed for 16 h. The solution was concentrated under a reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane-AcOEt (2/1-1/1). The titled compound was obtained as yellow oil (871 mg, 65%), and 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester was obtained as yellow oil (345 mg, 26%). 1H NMR (CDCl3) delta1.39 (t, 3H, J=7.1 Hz), 1.84-1.91 (m, 2H), 2.02-2.09 (m, 2H), 2.82 (t, 2H, J=6.4 Hz), 4.22 (t, 2H, J=6.2 Hz), 4.39 (q, 2H, J=7.1 Hz), 6.53 (s, 1H).

References: [1]Patent: US2006/276445,2006,A1 .Location in patent: Page/Page column 19.

12
tetrahydropyridino[1,2-c][1,2,3]oxadiazolone [ No CAS ]
[ 623-47-2 ]
[ 307307-84-2 ]
[ 118055-06-4 ]

Yield	Reaction Conditions	Operation in experiment
26%	In o-xylene;	Step 2 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid ethylester Ethyl propiolate (804 mg) was added to the o-xylene (15 mL) solution of tetrahydropyridino[1,2-c][1,2,3]oxadiazolone (1.04 g) under a nitrogen atmosphere and refluxed for 16 h. The solution was concentrated under a reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane-AcOEt (2/1-1/1). The titled compound was obtained as yellow oil (871 mg, 65%), and 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester was obtained as yellow oil (345 mg, 26%). 1H NMR (CDCl3) delta 1.39 (t, 3H, J=7.1 Hz), 1.84-1.91 (m, 2H), 2.02-2.09 (m, 2H), 2.82 (t, 2H, J=6.4 Hz), 4.22 (t, 2H, J=6.2 Hz), 4.39 (q, 2H, J=7.1 Hz), 6.53 (s, 1H).

References: [1]Patent: US2004/132708,2004,A1 .

13
[ 307307-84-2 ]
[ 1222956-55-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sulfuric acid; nitric acid; at 0 - 20℃;	Fuming nitric acid (20 ml_) was slowly added at 0Q C to cone sulfuric acid (20 ml_). This nithc-sulfuhc acid solution was then slowly added to reference example 15 (4.5 g, 23.4 mmol), previously cooled in an ice-bath. The mixture was then allowed to reach room temperature and stirred overnight. It was then poured over ice and extracted twice with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The residue was purified by chromatography over silica gel using hexane/EtOAc mixtures of increasing polarity as eluent, to afford 3.97 g of the desired compound (yield: 70%). LC-MS (Method 2): tR = 1.89 min; m/z = 240 (MH+).

References: [1]Patent: WO2010/43633,2010,A1 .Location in patent: Page/Page column 102.

14
[ 307307-84-2 ]
3-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid [ No CAS ]