474432-57-0|Pyrazolo[1,5-a]pyridin-5-ylmethanol| Ambeed

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Quality Control of [ 474432-57-0 ] Purity: 95% SDS Specification

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Product Details of [ 474432-57-0 ]

CAS No. :	474432-57-0
Formula :	C₈H₈N₂O
M.W :	148.16
SMILES Code :	OCC1=CC2=CC=NN2C=C1
MDL No. :	MFCD12828624

Safety of [ 474432-57-0 ]

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

Application In Synthesis of [ 474432-57-0 ]

* 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 [ 474432-57-0 ]

[ 474432-57-0 ] Synthesis Path-Downstream 1~34

1
[ 474432-57-0 ]
[ 474432-59-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With manganese(IV) oxide; In dichloromethane; at 20.0℃; for 20.0h;	To a solution of compound B-247 (1 .0 g, 6.7 mmol) in dichloromethane (10 mL) was added manganese dioxide (5.9 g, 67 mmol). The mixture was stirred at room temperature for 20 hours. On completion, the mixture was filtered, and the resulting filtrate was concentrated to give compound B-248 (0.70 g, 71 % yield) as a white solid. LCMS: (ES+) m/z (M+H)+ = 147.0, tR = 0.837.

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4594 - 4597.
[2]Patent: WO2015/66371,2015,A1 .Location in patent: Paragraph 00492-00493.

2
[ 474432-56-9 ]
[ 474432-57-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	With hydrogen bromide; at 120.0℃; for 12.0h;	A mixture of compound B-246 (2.0 g, 9.7 mmol) in 40% hydrobromic acid (20 mL) was heated to 120 C and stirred for 12 hours. On completion, the mixture was concentrated, neutralized with sodium carbonate, and extracted with dichloromethane (3 chi 50 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by silica gel chromatography (dichloromethane: methanol = 100: 1-10: 1 ) to give compound B-247 (1.0 g, 69% yield) as a yellow solid. LCMS: (ES+ ) m/z (M+H)+ = 149.0, tR = 1.146
60%		5-Hydroxymethylpyrazolo[1,5-a]pyridine (C4e); A mixture of 402 mg (1.95 mmol) methyl 5-hydroxymethylpyrazolo[1,5-a]pyridine-3-carboxylate (C3d) and 13.6 ml sulphuric acid (40%) was refluxed for 3 hrs and neutralized with 5N NaOH solution after cooling to room temperature. The solution was extracted with dichloromethane, the organic layers were dried with Na2SO4, evaporated and purified by flash-chromatography (EtOAc). Yield: 289 mg (60 %) yellow solid. Mp.: 47C. MS (EI): m/z 148 (M)+. IR (NaCl) v (cm-1): 3335; 2849; 1648; 1439; 1339; 1054; 774. 1H NMR (CDCl3, 360 MHz) delta (ppm): 2.12 (br s, 1H, OH); 4.70 (s, 2H, CH2); 6.46 (dd, J = 2.2 Hz, 0.8 Hz, 1H, H-3); 6.71 (dd, J = 7.2 Hz, 1.7 Hz, 1 H, H-6); 7.48 (dd, J = 1.7 Hz, 0.8 Hz, 1 H, H-4); 7.92 (d, J = 2.2 Hz, 1H, H-2); 8.40 (d, J = 7.2 Hz, 1 H, H-7).
		A suspension of methyl 5-(hydroxymethyl)pyrazolo[1 ,5-a]pyridine-3-carboxylate Y-6 (1.9 g, 9.1 mmol ) in 40% H2S04 was stirred at 80C for 24 h, then neutralized with 3N NaOH to pH=7-8. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04 and concentrated. The residue was purified by silica gel chromatography to afford the title compound (1.1g). MS (m/z): 149(M+1 ) +.

Pyrazolo[1,5-a]pyridin-5-ylmethanol (Y-7) A suspension of methyl 5-(hydroxymethyl)pyrazolo[1,5-a]pyridine-3-carboxylate Y-6 (1.9 g, 9.1 mmol) in 40% H2SO4 was stirred at 80 C. for 24 h, then neutralized with 3N NaOH to pH=7-8. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford the title compound (1.1 g). MS (m/z): 149 (M+1)+.

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4594 - 4597.
[2]Patent: WO2015/66371,2015,A1 .Location in patent: Paragraph 00490-00491.
[3]Patent: EP1972628,2008,A1 .Location in patent: Page/Page column 30.
[4]Patent: WO2011/79804,2011,A1 .Location in patent: Page/Page column 44.
[5]Patent: US2012/245178,2012,A1 .Location in patent: Page/Page column 27.
[6]Journal of Medicinal Chemistry,2014,vol. 57,p. 7577 - 7589.

3
[ 474432-57-0 ]
[ 104468-87-3 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4594 - 4597.

4
[ 474432-57-0 ]
pyrazolo[1,5-a]pyridine-5-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4594 - 4597.

5
[ 474432-57-0 ]
pyrazolo[1,5-<i>a</i>]pyridine-5-carboxylic acid {4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4594 - 4597.

6
1-amino-4-hydroxymethyl-pyridinium; methanesulfonate [ No CAS ]
[ 474432-57-0 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4594 - 4597.

7
[ 109-64-8 ]
[ 474432-57-0 ]
[ 1060724-95-9 ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In water; at 20.0℃;	5-(3-Bromopropoxymethyl)pyrazolo[1,5-a]pyridine (C6f); To a solution of 290 mg (7.25 mmol) NaOH in 0.60 ml water 173 mg (1.17 mmol) <strong>[474432-57-0]5-hydroxymethylpyrazolo[1,5-a]pyridine</strong> (C4e), 0.75 ml (7.31 mmol) 1,3-dibromopropane and 23.8 mg (0.07 mmol) tetrabutylammonium hydrogensulfate was added. After stirring over night at room temperature, water was added and the mixture was extracted with hexane. The organic layer was washed with brine, dried with Na2SO4, evaporated and purified by preparative HPLC (RP-18; H2O with 0.1% TFA 100% to MeCN 100%). Yield: 88 mg (28 %) light yellow oil. MS (EI): m/z 270 (M+1)+, 268 (M-1)+. IR (NaCl) v (cm-1): 3088; 2962; 2858; 1645; 1516; 1257; 1101; 783. 1H NMR (CDCl3, 600 MHz) delta (ppm): 2.14-2.18 (m, 2H, CH2CH2Br); 3.56 (t, J = 5.8 Hz, 2H, CH2Br); 3.65 (t, J = 6.4 Hz, 2H, OCH2CH2); 4.53 (s, 2H, CH2O); 6.48 (d, J = 2.0 Hz, 1H, H-3); 6.72 (dd, J = 7.2 Hz, 1.5 Hz, 1H, H-6); 7.47-7.48 (m, 1H, H-4); 7.94 (d, J = 2.0 Hz, 1H, H-2); 8.43 (d, J = 7.2 Hz, 1H, H-7). 13C NMR (CDCl3, 360 MHz) delta (ppm): 30.4; 32.8; 68.0; 72.0; 96.8; 111.4; 115.7; 128.6; 134.2; 139.9; 142.3.

References: [1]Patent: EP1972628,2008,A1 .Location in patent: Page/Page column 35.

8
[ 586-95-8 ]
[ 474432-57-0 ]

References: [1]Patent: WO2011/79804,2011,A1 .
[2]Patent: US2012/245178,2012,A1 .
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 7577 - 7589.
[4]Patent: WO2015/66371,2015,A1 .

9
[ 117423-41-3 ]
[ 474432-57-0 ]

References: [1]Patent: WO2011/79804,2011,A1 .
[2]Patent: US2012/245178,2012,A1 .
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 7577 - 7589.

10
[ 1313726-18-9 ]
[ 474432-57-0 ]

References: [1]Patent: WO2011/79804,2011,A1 .
[2]Patent: US2012/245178,2012,A1 .

11
[ 1313726-19-0 ]
[ 474432-57-0 ]

References: [1]Patent: WO2011/79804,2011,A1 .
[2]Patent: US2012/245178,2012,A1 .
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 7577 - 7589.

12
1-amino-4-((tert-butyldimethylsilyloxy)methyl)pyridinium 2,4-dinitrophenolate [ No CAS ]
[ 474432-57-0 ]