[ CAS No. 113293-71-3 ] {[proInfo.proName]}

Name: 113293-71-3|(6-Aminopyridin-3-yl)methanol|98%
Brand: Ambeed
SKU: A127666
Price: 15.0 USD
Availability: InStock
Rating: 91 (32 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 113293-71-3

Structure of 113293-71-3 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 113293-71-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 113293-71-3 ]

SDS Specification

Alternatived Products of [ 113293-71-3 ]

Product Details of [ 113293-71-3 ]

CAS No. :	113293-71-3	MDL No. :	MFCD06659089
Formula :	C₆H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TXPRFSOGPYITOT-UHFFFAOYSA-N
M.W :	124.14	Pubchem ID :	2794829
Synonyms :

Calculated chemistry of [ 113293-71-3 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.77
TPSA :	59.14 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) :	-7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.03
Log Po/w (XLOGP3) :	-0.23
Log Po/w (WLOGP) :	0.01
Log Po/w (MLOGP) :	-0.34
Log Po/w (SILICOS-IT) :	0.49
Consensus Log Po/w :	0.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.89
Solubility :	15.9 mg/ml ; 0.128 mol/l
Class :	Very soluble
Log S (Ali) :	-0.55
Solubility :	34.6 mg/ml ; 0.279 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.45
Solubility :	4.39 mg/ml ; 0.0354 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.36

Safety of [ 113293-71-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 113293-71-3 ]

* 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 [ 113293-71-3 ]
Downstream synthetic route of [ 113293-71-3 ]

[ 113293-71-3 ] Synthesis Path-Upstream 1~6

1
[ 3167-49-5 ]
[ 113293-71-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: for 16 h; Heating / reflux Stage #2: With sodium carbonate In ethanol; water	Concentrated sulfuric acid (0.95 ml, 17.2 mmol, 0.5 equiv) is added to a solution of 6- aminonicotinic acid (5.0 g, 34.4 mmol) in ethanol (50 ml). After heating to reflux for 16 hours, the reaction mixture is carefully poured into a concentrated aqueous Na₂CO₃ solution. The aqueous phase is extracted three times with EtOAc. The combined organic layers are washed with brine, dried over Na₂SO₄, filtered and concentrated in vacuo. The residue is dissolved in anhydrous THF (25 ml). At -60 ⁰C, lithium aluminium hydride (2.68 g, 68.6 mmol, 3.0 equiv) is carefully added. The mixture is warmed to 0 ⁰C, and then refluxed for 1 hour. After cooling, water (1.5 ml) and 5 N aqueous NaOH solution (1.5 ml) are added. The precipitate is filtered off, and the filtrate is concentrated in vacuo. The residue is purified via flash chromatography (EtOAc / MeOH 95 : 5) to afford the title compound (2.15 g, 72percent). ¹H NMR (400 MHz, d₆-DMSO): δ = 7.82 (d, J = 1.7 Hz, 1H), 7.32 (dd, J = 8.3 / 2.5 Hz, 1 H), 6.40 (dd, J = 9.3 / 1.0 Hz, 1 H), 5.77 (br s, 2H), 4.88 (t, J = 5.5 Hz, 1 H), 4.27 (d, J = 5.5 Hz, 2H). MS (ES⁺): 125 (M+H)⁺.

Reference： [1] Patent: WO2008/74752, 2008, A2, . Location in patent: Page/Page column 27-28
[2] Patent: EP1798221, 2007, A1, . Location in patent: Page/Page column 32
[3] Patent: EP1956013, 2008, A1, . Location in patent: Page/Page column 30-31
[4] Patent: US2007/99930, 2007, A1, . Location in patent: Page/Page column 42
[5] Patent: WO2013/13817, 2013, A1,
[6] Patent: WO2013/13815, 2013, A1,
[7] Patent: US2013/29961, 2013, A1,
[8] Patent: US2013/29962, 2013, A1,

2
[ 39658-41-8 ]
[ 113293-71-3 ]

Reference： [1] Tetrahedron Letters, 1990, vol. 31, # 40, p. 5757 - 5760
[2] Patent: WO2013/13817, 2013, A1, . Location in patent: Page/Page column 141
[3] Patent: WO2013/13815, 2013, A1, . Location in patent: Page/Page column 208; 209
[4] Patent: US2013/29961, 2013, A1, . Location in patent: Paragraph 0809
[5] Patent: US2013/29962, 2013, A1, . Location in patent: Paragraph 1032

3
[ 36052-24-1 ]
[ 113293-71-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran Stage #2: With methanol In tetrahydrofuran at 0℃;	Compound 15 (1.0 equiv., 3.94 mmol, 0.600 g) was added portion wise to a suspension OfLiAlH₄ (3.00 equiv., 11.83 mmol, 0.449 g) in dry THF (17 ml) at 0⁰C. The reaction mixture was stirred at room temperature overnight. Excess LiAlH₄ was destroyed by addition of methanol (while cooling on ice), the reaction mixture was filtered over Celite and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography (dichloromethane / methanol 75:25) to give 6-amino-3-pyridinemethanol (16) (0.330 g, yield = 67percent) as a white solid. ¹H NMR (δ, CD₃OD): 4.43 (2H, s), 6.58 (IH, d, J = 8.5 Hz), 7.48 (IH, dd, J = 8.5, ~ 2 Hz) 7.86 (IH, d, J ~ 2 Hz)

Reference： [1] Patent: WO2007/113290, 2007, A1, . Location in patent: Page/Page column 28

4
[ 866561-42-4 ]
[ 113293-71-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With hydrazine In methanol for 2 h; Heating / reflux	To a solution of acetic acid 6- (1, 3- dioxo-1, 3-dihydroisoindol-2-yl) pyridin-3-ylmethyl ester (0.200g, 0. 675mmol) was added methanol (lOmL). Hydrazine (0.065g, 2. 03mmol) was added and the mixture was heated to reflux for 2 hrs. A white precipitate formed after 30 min. The reaction was cooled to room temperature and filtered. The filtrate was concentrated and the residue was chromatographed on silica gel (Biotage 15,15percent 7N methanol ammonium/dichloromethane) to give 0.025g (30percent) of the title compound as clear oil. LCMS (APCI+) RT=0. 31 min. m/z 125 (M+H) +.

Reference： [1] Patent: WO2005/95391, 2005, A1, . Location in patent: Page/Page column 37-38
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2206 - 2210

5
[ 329-89-5 ]
[ 113293-71-3 ]

Reference： [1] Tetrahedron Letters, 1990, vol. 31, # 40, p. 5757 - 5760

6
[ 107-20-0 ]
[ 113293-71-3 ]
[ 132213-07-1 ]

Reference： [1] Tetrahedron Letters, 1990, vol. 31, # 40, p. 5757 - 5760

[ 113293-71-3 ] Synthesis Path-Downstream 1~55

1
[ 107-20-0 ]
[ 113293-71-3 ]
[ 132213-07-1 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 5757 - 5760

2
[ 39658-41-8 ]
[ 113293-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	To a stirred solution of lithium aluminium hydride (73 mg, 1.93 mmol) in tetrahydrofuran was slowly added solution of ethyl 6-aminonicotinate (80 mg, 0.48 mmol) in tetrahydrofuran at 0 C under nitrogen. The reaction mixture was stirred at 0 C for 30 minutes then at room temperature for 3 h. The mixture was quenched at 0 C with 1N HCI until pH is 3 then basified with sodium carbonate solution until pH is 7. Then the mixture was filtered using celite to remove LAH residue and it was dissolved in ethylacetate and washed with saturated sodium carbonate solution. The organic layer was dried over MgS04 and filtered. The filtrate was removed in vacuo. The crude condition of (6-aminopyridin-3- yl)methanol (30 mg, crude) was obtained in 50 % yield.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 23℃; for 3.5h;Inert atmosphere;	To a stirred solution of lithium aluminium hydride (183 mg, 4.83 mmol) in tetrahydrofuran was slowly added solution of ethyl 6-aminonicotinate (200 mg, 1.21 mmol) in tetrahydrofuran at 0 C under nitrogen atmosphere. The reaction mixture was stirred at 0 C for 30 minutes then at room temperature for 3 h. The mixture was quenched at 0 C with 1 HCI until pH is 3 then basified with sodium carbonate solution until pH is 7. Then the mixture was filtered using celite to remove LAH residue and it was dissolved in ethyl acetate and washed with saturated sodium carbonate solution. The organic layer was dried (magnesium sulphate) and filtered. The filtrate was removed in vacuo. The crude condition of (6- aminopyridin-3-yl)methanol (55 mg, crude) was obtained in 75 % yield.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 3.5h;Inert atmosphere;	Step 2: To a stirred solution of lithium aluminium hydride (73 mg, 1.93 mmol) in tetrahydrofuran was slowly added solution of ethyl 6-aminonicotinate (80 mg, 0.48 mmol) in tetrahydrofuran at 0 C. under nitrogen. The reaction mixture was stirred at 0 C. for 30 minutes then at room temperature for 3 h. The mixture was quenched at 0 C. with 1N HCl until pH is 3 then basified with sodium carbonate solution until pH is 7. Then the mixture was filtered using celite to remove LAH residue and it was dissolved in ethylacetate and washed with saturated sodium carbonate solution. The organic layer was dried over MgSO4 and filtered. The filtrate was removed in vacuo. The crude condition of (6-aminopyridin-3-yl)methanol (30 mg, crude) was obtained in 50% yield.

With hydrogenchloride; lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 3.5h;Inert atmosphere;

Step 2 To a stirred solution of lithium aluminium hydride (183 mg, 4.83 mmol) in tetrahydrofuran was slowly added solution of ethyl 6-aminonicotinate (200 mg, 1.21 mmol) in tetrahydrofuran at 0 C. under nitrogen atmosphere. The reaction mixture was stirred at 0 C. for 30 minutes then at room temperature for 3 h. The mixture was quenched at 0 C. with 1N HCl until pH is 3 then basified with sodium carbonate solution until pH is 7. Then the mixture was filtered using celite to remove LAH residue and it was dissolved in ethyl acetate and washed with saturated sodium carbonate solution. The organic layer was dried (magnesium sulfate) and filtered. The filtrate was removed in vacuo. The crude condition of (6-aminopyridin-3-yl)methanol (55 mg, crude) was obtained in 75% yield.

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 5757 - 5760
[2]Patent: WO2013/13817,2013,A1 .Location in patent: Page/Page column 141
[3]Patent: WO2013/13815,2013,A1 .Location in patent: Page/Page column 208; 209
[4]Patent: US2013/29961,2013,A1 .Location in patent: Paragraph 0809
[5]Patent: US2013/29962,2013,A1 .Location in patent: Paragraph 1032

3
[ 36052-24-1 ]
[ 113293-71-3 ]

Yield	Reaction Conditions	Operation in experiment
67%		Compound 15 (1.0 equiv., 3.94 mmol, 0.600 g) was added portion wise to a suspension OfLiAlH4 (3.00 equiv., 11.83 mmol, 0.449 g) in dry THF (17 ml) at 00C. The reaction mixture was stirred at room temperature overnight. Excess LiAlH4 was destroyed by addition of methanol (while cooling on ice), the reaction mixture was filtered over Celite and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography (dichloromethane / methanol 75:25) to give 6-amino-3-pyridinemethanol (16) (0.330 g, yield = 67%) as a white solid. 1H NMR (delta, CD3OD): 4.43 (2H, s), 6.58 (IH, d, J = 8.5 Hz), 7.48 (IH, dd, J = 8.5, ~ 2 Hz) 7.86 (IH, d, J ~ 2 Hz)
2.6 g	With lithium aluminium tetrahydride; In tetrahydrofuran; at 70℃; for 16h;Inert atmosphere;	Under the protection of nitrogen gas, a solution of methyl 6-aminopyridine-3-formate (5.00 g) in tetrahydrofuran (50 mL) was added to a solution of LiAlH4 (1.5 g) in tetrahydrofuran (100 mL), and the mixture was stirred at 70 C. for 16 hours. TLC showed that the reaction was complete. The mixture was cooled to 20 C. Water (1.5 mL), an aqueous solution of sodium hydroxide (15%, 1.5 mL) and water (4.5 mL) were added sequentially and stirred for 0.5 hours. The mixture was filtered. The filtrate was concentrated to give a yellow solid, which was washed with (petroleum ether:ethyl acetate=1:10). The residual yellow solid was the compound of formula (a-1) (2.6 g).

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1341 - 1345
[2]Patent: WO2007/113290,2007,A1 .Location in patent: Page/Page column 28
[3]Patent: US2019/194168,2019,A1 .Location in patent: Paragraph 0147; 0148

4
[ 329-89-5 ]
[ 113293-71-3 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 5757 - 5760

5
[ 113293-71-3 ]
[ 132213-03-7 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 5757 - 5760

6
[ 113293-71-3 ]
[ 230617-81-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With thionyl chloride; In tetrahydrofuran; for 0.5h;	To a 25mL flask was added (6-aminopyridin-3-yl) methanol (0.025g, 0. 20mmol) and tetrahydrofuran (5mL). Thionyl chloride (0.048g, 0. 405mmol) was added with vigorous stirring. The mixture was stirred for 30 min and concentrated to dryness to afford 0.035g (60%, 60% by weight) of the title compound as a bright yellow solid.'H NMR (400MHz, DMSO) 8 7. 82 (s, 1H, Ar-H), 7.32 (d, 1H, J=8. 20Hz, Ar-H), 6.42 (d, 1H, J=8. 20Hz, Ar-H), 5.69 (s, 2H, Ar-NH2), 4.09 (s, 2H, Ar-CH-Cl).

Reference： [1]Patent: WO2005/95391,2005,A1 .Location in patent: Page/Page column 38

7
[ 866561-42-4 ]
[ 113293-71-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With hydrazine; In methanol; for 2h;Heating / reflux;	To a solution of acetic acid 6- (1, 3- dioxo-1, 3-dihydroisoindol-2-yl) pyridin-3-ylmethyl ester (0.200g, 0. 675mmol) was added methanol (lOmL). Hydrazine (0.065g, 2. 03mmol) was added and the mixture was heated to reflux for 2 hrs. A white precipitate formed after 30 min. The reaction was cooled to room temperature and filtered. The filtrate was concentrated and the residue was chromatographed on silica gel (Biotage 15,15% 7N methanol ammonium/dichloromethane) to give 0.025g (30%) of the title compound as clear oil. LCMS (APCI+) RT=0. 31 min. m/z 125 (M+H) +.

Reference： [1]Patent: WO2005/95391,2005,A1 .Location in patent: Page/Page column 37-38
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2206 - 2210

8
[ 13057-17-5 ]
[ 113293-71-3 ]
[ 935687-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 2.5h;	B. 5-Methoxymethoxymethyl-pyridin-2-ylamine; Bromomethyl methyl ether (0.25 mL, 3.06 mmol) was added dropwise to a cold (0 C.) solution of the compound prepared in Part A (0.222 g, 1.79 mmol) and N,N-diisopropylethylamine (0.47 mL, 2.68 mmol) in CH2Cl2 (10 mL). The resulting mixture stirred at 0 C. for 2½ hr, water was added and layers separated. The CH2Cl2 layer was dried over MgSO4, filtered and evaporated in vacuo to give the desired MOM protected amino pyridine product.

Reference： [1]Patent: US2007/99930,2007,A1 .Location in patent: Page/Page column 42

9
[ 929899-17-2 ]
[ 113293-71-3 ]
[ 929898-44-2 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of (6-ami?o-pyridin-3-yl)-methanol (102.5 mg, 0.819 mmol) and 2-bromo-i-[4-(1-methyl-5-trifluoromethyl-1H-pyrazo]-3-yl)-pheny]]-ethano?e (258 mg, 0.744 mmol) in DCE (15 mL) was heated at 80 6C for 16 h. NaHCO3 (62 mg, 0.74 mmol) was added to the EPO <DP n="39"/>reaction mixture, which was continued heating for 1 d. The resulting orange solution was cooled and white solid feil out of solution. The mixture was filtered to provide 120,7 mg of {2- [4-{1 -methyl-5-trifluoromethyI-1 H-pyrazol-3-yl)-phenyl]-irnidazo[1 ,2-a]pyridin-6-yl}-r?ethanol as a white solid. MS: (M*) 373. 1H NMR (400 MHz1 CD3OD); delta 8.41 (s, 1), 8.23 (s, 1), 7.98 (d, 2, J = 8.5), 7.90 (d, 2, J = 8.5), 7.54 (d, 1, J - 9.3), 7.33 (dd, 1 , J = 9.3, 1.7), 7.19 (s, 1), 4.64 (s, 2), 4,05 (s, 3).(C3a IC50 = 84 nM) racemic, (C3a IC50 = 63 nM), (C3a IC50 = 75 nM) enantiomers

Reference： [1]Patent: WO2007/34278,2007,A2 .Location in patent: Page/Page column 37-38

10
[ 3167-49-5 ]
[ 113293-71-3 ]

Yield	Reaction Conditions	Operation in experiment
72%		Concentrated sulfuric acid (0.95 ml, 17.2 mmol, 0.5 equiv) is added to a solution of 6- aminonicotinic acid (5.0 g, 34.4 mmol) in ethanol (50 ml). After heating to reflux for 16 hours, the reaction mixture is carefully poured into a concentrated aqueous Na2CO3 solution. The aqueous phase is extracted three times with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue is dissolved in anhydrous THF (25 ml). At -60 0C, lithium aluminium hydride (2.68 g, 68.6 mmol, 3.0 equiv) is carefully added. The mixture is warmed to 0 0C, and then refluxed for 1 hour. After cooling, water (1.5 ml) and 5 N aqueous NaOH solution (1.5 ml) are added. The precipitate is filtered off, and the filtrate is concentrated in vacuo. The residue is purified via flash chromatography (EtOAc / MeOH 95 : 5) to afford the title compound (2.15 g, 72%). 1H NMR (400 MHz, d6-DMSO): delta = 7.82 (d, J = 1.7 Hz, 1H), 7.32 (dd, J = 8.3 / 2.5 Hz, 1 H), 6.40 (dd, J = 9.3 / 1.0 Hz, 1 H), 5.77 (br s, 2H), 4.88 (t, J = 5.5 Hz, 1 H), 4.27 (d, J = 5.5 Hz, 2H). MS (ES+): 125 (M+H)+.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃;	(1) At 0C, lithiumaluminium hydride (1.7 g) was added to a THF solution (58 mL) of 6-amino-nicotinic acid (2.0 g), and stirred overnight at room temperature. Sodium sulfate 10 hydrate was added to the reaction liquid at 0C to stop the reaction, and this was dried with anhydrous sodium sulfate. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain (6-amino-3-pyridinyl)methanol (1.7 g) as a brown solid. ESI-MS Found: m/z 125[M+H]+.
		Example 20 5-{4-[6-(Fluoromethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole (86) 6-Aminonicotinic acid (830 mg) was dissolved in tetrahydrofuran (20 mL), and borane-tetrahydrofuran complex (12 mL) was added to the solution, followed by refluxing under nitrogen for 4 hours. Subsequently, 2.4N hydrochloric acid solution (10 mL) and methanol (10 mL) were gradually added to the mixture, followed by heating at 80C for 1 hour. After the mixture had been left to cool, the mixture was alkalified with 2N sodium hydroxide solution and extracted with dichloromethane-methanol, followed by purification, to thereby yield (6-amino-3-pyridyl)methanol (562 mg). Thereafter, this product was dissolved in ethanol (35 mL), and 2-bromo-1-[4-(1,3-oxazol-5-yl)phenyl]-1-ethanone (857 mg), which had been produced in Referential Example 10, was added to the solution. Subsequently, sodium hydrogencarbonate (271 mg) was further added to the mixture, followed by refluxing for 14 hours. Water (10 mL) was added to the reaction mixture, and the mixture was left to cool, followed by recovering the precipitated matter through filtration and then drying, to thereby yield {2-[4-(1,3-oxazol-5-yl)phenyl]imidazo[1,2-a]pyridin-6-yl}methanol (664 mg). Thereafter, 47% hydrobromic acid (6 mL) and concentrated sulfuric acid (600 muL) were added to {2-[4-(1,3-oxazol-5-yl)phenyl]imidazo[1,2-a]pyridin-6-yl}methanol (170 mg), and the mixture was refluxed for 4 hours. After the mixture had been left to cool, the mixture was alkalified with 2N sodium hydroxide solution, and extracted with dichloromethane-methanol, followed by drying over sodium sulfate. The solvent was evaporated, and the residue was purified through silica gel chromatography (dichloromethane : methanol = 95 : 5), followed by concentration under reduced pressure, to thereby yield 5-{4-[6-(bromomethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole (169 mg). The thus-obtained 5-{4-[6-(bromomethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole (71 mg) was dissolved in dimethylsulfoxide (1.0 mL), and tetrabutylammonium fluoride (1M tetrahydrofuran solution, 2.0 mL) was added to the solution. The procedure of Example 19 was repeated, to thereby yield the title compound (15 mg). 1H-NMR(400MHz,DMSO-d6)delta:5.46(2H,d,J=47.8Hz), 7.34(1H,d,J=23.9Hz),7.64(1H,d,J=9.3Hz),7.75(1H,s), 7.81(2H,d,J=8.3Hz),8.09(2H,d,J=8.3Hz),8.48(1H,s),8.53(1H,s), 8.71(1H,d,J=3.4Hz). EI-MS m/z:293(M)+.

Example 30 3-[7-Fluoro-2-(4-fluoro-benzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-N-(5methoxymethoxymethyl-pyridin-2-yl)-propionamide A. (6-Amino-pyridin-3-yl)-methanol; To a cold (0 C.) mixture of 6-Aminonicotinic acid methyl ester (0.511 g, 3.36 mmol) and Cerium(III) chloride heptahydrate (1.25 g, 3.36) in dry THF was slowly added lithium borohydride (8.4 mL, 1 M in THF) over a 30 minute period. The mixture was allowed to warm to room temperature overnight then slowly quenched by the addition of ice water (20 mL). After stirring for 1 hr the mixture was filtered through Celite diluted with EtOAc (30 mL) and layers were separated. The aqueous layer was further extracted with EtOAc (1×). The combined EtOAc extracts were washed with brine, dried over MgSO4, evaporated in vacuo and provide a crude semi-solid. The white solid product was triturated with diethyl ether, filtered and dried under reduced pressure.

Reference： [1]Patent: WO2008/74752,2008,A2 .Location in patent: Page/Page column 27-28
[2]Patent: EP1798221,2007,A1 .Location in patent: Page/Page column 32
[3]Patent: EP1956013,2008,A1 .Location in patent: Page/Page column 30-31
[4]Patent: US2007/99930,2007,A1 .Location in patent: Page/Page column 42
[5]Patent: WO2013/13817,2013,A1
[6]Patent: WO2013/13815,2013,A1
[7]Patent: US2013/29961,2013,A1
[8]Patent: US2013/29962,2013,A1

11
6-aminonicotinic acid ethyl ester bishydrochloride [ No CAS ]
[ 113293-71-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a slurry of 6-amino-nicotinic acid ethyl ester bis HCl salt (17.21 g, 72.06 mmol) in THF (350 mL) at 0 C was added LAH (11.0 g, 2S9 mmol). Gas evolution was observed. The cold bath was removed and the reaction was allowed to warm to rt over 3 h. An additional portion of LAH (4.0 g, 105 mmol) was added. After 1.5 h the reaction mixture was cooled to 0C and 1 M aq NaOH (50 mL) was added slowly until gas evolution ceased. The mixture was warmed to rt and EtOAc and Na2SO4 were added. After stirring for 30 mi?, the mixture was filtered and concentrated. The crude solid was preabsorbed to silica gel and chromatographed using 10-15% MeOH in CH2CI2 to provide 5.19 g of (6-amino-pyridi?-3-yl)- methanol as a pale-yellow solid. 1H NMR (400 MHz, CD3OD): delta 7.84 (d, 2, J = 2.3), 7.48 (dd,1, J - 8.5, 2.3), 6.58 (d, 1, J = 8.3), 4.43 (s, 2).

Reference： [1]Patent: WO2007/34278,2007,A2 .Location in patent: Page/Page column 57

12
[ 113293-71-3 ]
[ 18162-48-6 ]
[ 936033-59-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With dmap; In N,N-dimethyl-formamide; at 20℃; for 24h;	2-Arnino-5-rfe/Y-butyldimethylsilyloxymethyl)pyridine hydrochloride A mixture of <strong>[113293-71-3]6-amino-3-(hydroxymethyl)pyridine</strong> (80 mg, 0.64 mmol), chloro- (fert-butyl)dimethylsilane (107 mg, 0.71 mmol) and DMAP (4.0 mg, 0.032 mmol) in DMF (1 mL) was stirred at rt for 24 h. The mixture was diluted with toluene (10 mL) and the precipitate formed was filtered off, washed with toluene (10 mL) and dried in vacuo. Yield: 121 mg (69%) of white plates. <n="63"/>1H NMR (DMSOd65 400 MHz) delta 13.78-13.45 (br. s, IH), 8.04 (s, 2H), 7.9-7.8 (m, 2H), 7.01 (d, IH), 4.58 (s, 2H), 0.89 (s, 9H)S 0.09 (s, 6H).

Reference： [1]Patent: WO2007/51981,2007,A1 .Location in patent: Page/Page column 61-62

13
[ 113293-71-3 ]
[ 18162-48-6 ]
[ 322691-19-0 ]

Yield	Reaction Conditions	Operation in experiment
89.0%	With N-ethyl-N,N-diisopropylamine;dmap; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; for 20h;	<strong>[113293-71-3](6-Amino-pyridin-3-yl)-methanol</strong> (1.00 g, 8.06 mmol) was dissolved in a mixture of DCM/DMF (v/v 4:1, 5OmL) with stirring, and cooled to 0C. N,N- diisopropylethylamine(1.99 niL, 12.09 mmol), tert-butyl-chloro-dimethyl-silane(1.67 g, 11.1 mmol) and 4-dimethylaminopyridine (0.02 g, 0.16 mmol ) were added. Stirred at rt for 20 hours. The reaction mixture was concentrated under rotary evaporation and partitioned in EtOAc (3OmL) and water (3OmL). The organic layer was rinsed with water (2OmL), and then a saturated sodium chloride solution (2OmL), dried over sodium sulfate, filtered, and concentrated to yellow oil. After chromatography on silica gel with a gradient from 10-100% <n="128"/>ethyl acetate-hexanes, 5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamine (1.71 g, 89.0% yield) was obtained as white crystals. 1H NMR (300 MHz, OMSO-Jt6): delta 7.78 (s, 1 H), 7.35 (d, J = 6.0 Hz, 1 H)5 6.35 (d. J= 6.0 Hz, 1 H), 5.80 (s, 2 H). 4.45 (s, 2 H), 0.80 (s, 9 H). 0.00 (s, 6 H); LCMS (m/z): 239.4 [C12H22N2OS + H] +.
	With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃; for 1h;	(2) At 0C, tert-butyldimethylsilyl chloride (243 mg) was added to a DMF solution (1.6 mL) of the obtained compound (200 mg) and imidazole (329 mg), and stirred at room temperature for 1 hour. Aqueous sodium hydrogencarbonate solution was added to the reaction liquid to stop the reaction, and this was extracted with diethyl ether. The organic layer was washed with water and saturated saline water, and then dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified through thin-layer silica gel chromatography (hexane/ethyl acetate = 2/8) to obtain 5-([tert-butyl(dimethyl)silyl]oxy}methyl)-2-pyridinamine (220 mg) as a white solid. ESI-MS Found: m/z 239[M+H]+.
35 mg	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 5h;	To a stirred solution of <strong>[113293-71-3](6-aminopyridin-3-yl)methanol</strong> (30 mg, 0.24 mmol) in dimethylformamide were added imidazole (33 mg, 0.48 mmol) and tert- butyldimethylchlorosilane (36 mg, 0.24 mmol). The reaction mixture was stirred at room temperature for 5 h. The mixture was dissolved in ethylacetate and washed with water several times to remove dimethylformamide residue. The organic layer was dried over MgSCX, and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography. 5-((tert-butyldimethylsilyloxy)methyl)pyridin-2-amine (35 mg) was obtained in 35 % yield.

44 mg	With 1H-imidazole; In dichloromethane; at 23℃; for 5h;	To a stirred solution of <strong>[113293-71-3](6-aminopyridin-3-yl)methanol</strong> (55 mg, 0.44 mmol) in dimethylformamide were added imidazole (60 mg, 0.88 mmol) and tert- butyldimethylchlorosilane (66 mg, 0.44 mmol). The reaction mixture was stirred at room temperature for 5 h. The mixture dissolved in ethyl acetate and washed with water several times. The organic layer was dried over magnesium sulphate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography. 5-((tert- butyldimethylsilyloxy)methyl)pyridin-2-amine (44 mg) was obtained in 42 % yield.
35 mg	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 5h;	Step 3: To a stirred solution of <strong>[113293-71-3](6-aminopyridin-3-yl)methanol</strong> (30 mg, 0.24 mmol) in dimethylformamide were added imidazole (33 mg, 0.48 mmol) and tert-butyldimethylchlorosilane (36 mg, 0.24 mmol). The reaction mixture was stirred at room temperature for 5 h. The mixture was dissolved in ethylacetate and washed with water several times to remove dimethylformamide residue. The organic layer was dried over MgSO4 and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography. 5-((tert-butyldimethylsilyloxy)methyl)pyridin-2-amine (35 mg) was obtained in 35% yield.
44 mg	With 1H-imidazole; In ethyl acetate; at 20℃; for 5h;	Step 3 To a stirred solution of <strong>[113293-71-3](6-aminopyridin-3-yl)methanol</strong> (55 mg, 0.44 mmol) in dimethylformamide were added imidazole (60 mg, 0.88 mmol) and tert-butyldimethylchlorosilane (66 mg, 0.44 mmol). The reaction mixture was stirred at room temperature for 5 h. The mixture dissolved in ethyl acetate and washed with water several times. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography. 5-((tert-butyldimethylsilyloxy)methyl)pyridin-2-amine (44 mg) was obtained in 42% yield.

Reference： [1]Patent: WO2009/23718,2009,A2 .Location in patent: Page/Page column 125-127
[2]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1341 - 1345
[3]Patent: EP1798221,2007,A1 .Location in patent: Page/Page column 32
[4]Patent: WO2013/13817,2013,A1 .Location in patent: Page/Page column 141
[5]Patent: WO2013/13815,2013,A1 .Location in patent: Page/Page column 209
[6]Patent: US2013/29961,2013,A1 .Location in patent: Paragraph 0810
[7]Patent: US2013/29962,2013,A1 .Location in patent: Paragraph 1033

14
[ 113293-71-3 ]
[ 58479-61-1 ]
[ 1034309-74-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;	Ethyl-diisopropyl-amine (1.47 ml, 8.4 mmol, 1.1 equiv) and tert-butyl-diphenylsilyl chloride (2.22 ml, 8.4 mmol, 1.1 equiv) are added to a solution of (6-amino-pyridin-3-yl)-methanol (1.0 g, 7.65 mmol) in N.N-dimethylformamide (10 ml). The reaction mixture is stirred for 2 hours at room temperature, before it is diluted with water and extracted three times with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified via flash chromatography (EtOAc / hexane 1 : 1) to afford the title compound (2.10 g, 72%). 1H NMR (400 MHz, de-DMSO): delta = 7.78 (s, 1H), 7.65 - 7.62 (m, 4H), 7.49 - 7.41 (m, 6H), 7.30 (dd, J = 8.4 / 2.4 Hz, 1H), 6.42 (d, J = 8.4 Hz, 1H), 5.87 (br s, 2H), 4.56 (s, 2H), 1.00 (s, 9H). MS (ES+): 363 (M+H)+.

Reference： [1]Patent: WO2008/74752,2008,A2 .Location in patent: Page/Page column 27

15
[ 938460-71-0 ]
[ 113293-71-3 ]
[ 938461-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In ethanol; for 14h;Heating / reflux;	Example 20 5-{4-[6-(Fluoromethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole (86) 6-Aminonicotinic acid (830 mg) was dissolved in tetrahydrofuran (20 mL), and borane-tetrahydrofuran complex (12 mL) was added to the solution, followed by refluxing under nitrogen for 4 hours. Subsequently, 2.4N hydrochloric acid solution (10 mL) and methanol (10 mL) were gradually added to the mixture, followed by heating at 80C for 1 hour. After the mixture had been left to cool, the mixture was alkalified with 2N sodium hydroxide solution and extracted with dichloromethane-methanol, followed by purification, to thereby yield (6-amino-3-pyridyl)methanol (562 mg). Thereafter, this product was dissolved in ethanol (35 mL), and 2-bromo-1-[4-(1,3-oxazol-5-yl)phenyl]-1-ethanone (857 mg), which had been produced in Referential Example 10, was added to the solution. Subsequently, sodium hydrogencarbonate (271 mg) was further added to the mixture, followed by refluxing for 14 hours. Water (10 mL) was added to the reaction mixture, and the mixture was left to cool, followed by recovering the precipitated matter through filtration and then drying, to thereby yield {2-[4-(1,3-oxazol-5-yl)phenyl]imidazo[1,2-a]pyridin-6-yl}methanol (664 mg). Thereafter, 47% hydrobromic acid (6 mL) and concentrated sulfuric acid (600 muL) were added to {2-[4-(1,3-oxazol-5-yl)phenyl]imidazo[1,2-a]pyridin-6-yl}methanol (170 mg), and the mixture was refluxed for 4 hours. After the mixture had been left to cool, the mixture was alkalified with 2N sodium hydroxide solution, and extracted with dichloromethane-methanol, followed by drying over sodium sulfate. The solvent was evaporated, and the residue was purified through silica gel chromatography (dichloromethane : methanol = 95 : 5), followed by concentration under reduced pressure, to thereby yield 5-{4-[6-(bromomethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole (169 mg). The thus-obtained 5-{4-[6-(bromomethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole (71 mg) was dissolved in dimethylsulfoxide (1.0 mL), and tetrabutylammonium fluoride (1M tetrahydrofuran solution, 2.0 mL) was added to the solution. The procedure of Example 19 was repeated, to thereby yield the title compound (15 mg). 1H-NMR(400MHz,DMSO-d6)delta:5.46(2H,d,J=47.8Hz), 7.34(1H,d,J=23.9Hz),7.64(1H,d,J=9.3Hz),7.75(1H,s), 7.81(2H,d,J=8.3Hz),8.09(2H,d,J=8.3Hz),8.48(1H,s),8.53(1H,s), 8.71(1H,d,J=3.4Hz). EI-MS m/z:293(M)+.

Reference： [1]Patent: EP1956013,2008,A1 .Location in patent: Page/Page column 30-31

16
[ 113293-71-3 ]
[ 866561-43-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2206 - 2210

17
[ 113293-71-3 ]
[ 128781-53-3 ]
[ 4637-24-5 ]
N-([(5S)-N-(4-[6-hydroxymethylimidazo[1,2-a]pyridin-3-ylcarbonyl]phenyl)-2-oxooxazolidin-5-yl]methyl)acetamide [ No CAS ]

Reference： [1]Patent: US6362191,2002,B1 .Location in patent: Page column 38

18
[ 76-83-5 ]
[ 113293-71-3 ]
[ 1227486-25-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In chloroform; N,N-dimethyl-formamide; at 0 - 20℃;	(6-Aminopyridin-3-yl)methanol (1.327 g) was dissolved in 20 mL of a 1/1 mixed solvent of CHCl3/DMF, followed by addition of triethylamine (2.24 mL). The reaction mixture was cooled to 0C and tritylchloride (3.13 g) which had been dissolved in CHCl3 (10 mL) was slowly added dropwise thereto. After completion of the dropwise addition, the reaction mixture was warmed to room temperature, followed by further stirring for 2 hours. The reaction mixture was concentrated under reduced pressure, followed by addition of EtOAc and water and being left to stand still at -10C overnight. Thereafter, the precipitated solid was collected by filtration and washed with water and cold EtOAc to collect [6-(tritylamino)pyridin-3-yl]methanol as a white solid by filtration. Further, the filtrate was extracted with EtOAc by a liquid separation operation. The organic layer was dried over Na2SO4 and then filtered, and the solvent was evaporated under reduced pressure. This residue was purified by silica gel column chromatography (CHCl3/MeOH = from 100/0 to 96/4) to obtain [6-(tritylamino)pyridin-3-yl]methanol as a white solid. A total amount of 6-(tritylamino)pyridin-3-yl]methanol obtained by collection by filtration and silica gel column chromatography as a white solid was 3.744 g.

Reference： [1]Patent: EP2361902,2011,A1 .Location in patent: Page/Page column 40

19
[ 113293-71-3 ]
[ 1227486-26-1 ]

Reference： [1]Patent: EP2361902,2011,A1

20
[ 113293-71-3 ]
[ 1227486-27-2 ]

Reference： [1]Patent: EP2361902,2011,A1

21
[ 113293-71-3 ]
[ 760155-78-0 ]

Reference： [1]Patent: EP2361902,2011,A1

22
[ 1184852-50-3 ]
[ 113293-71-3 ]
[ 1413913-22-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 8Synthesis of 2-cyano-N,N-dimethyl-3-(6-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2- ylamino)pyridin-3 -yl)acrylamideStep 1To a 35ml seal tube, l-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3- b]pyrazine-7-yl)-2,2-dimethylpropane-l-one (1.0 g, 0.00242 mole) and (6-aminopyridin-3- yl)methanol (0.36 g, 0.00291 mole) was taken in toluene(10.0 ml). The reaction mixture was purged with argon for 15min at RT followed by Cs2C03 (3.1 g, 0.0097 mole) was added and further purged for 30 min with argon. BINAP (0.03 g, 0.000048 mole) and Pd(OAc)2 (0.01 g, 0.000048 mole) were added and the reaction mixture was heated to 110 C for 16 hrs. After completion of the reaction, the reaction mixture was filtered through celite bed and washed with ethyl acetate. Filtrate was collected and concentrated to afford crude product which was purified using column purification by eluting the compound with 20-25% ethyl acetate in hexanes to yield 0.5 g of l-(2-(5-(hydroxymethyl)pyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)- 5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-l-one. Attorney Docket No. 11913-1008

Reference： [1]Patent: WO2012/158785,2012,A1 .Location in patent: Page/Page column 100

23
[ 113293-71-3 ]
[ 1018447-30-7 ]

Reference： [1]Patent: WO2013/13817,2013,A1
[2]Patent: WO2013/13815,2013,A1
[3]Patent: US2013/29961,2013,A1
[4]Patent: US2013/29962,2013,A1

24
[ 113293-71-3 ]
[ 1421473-29-1 ]

Reference： [1]Patent: WO2013/13817,2013,A1
[2]Patent: US2013/29961,2013,A1

25
[ 113293-71-3 ]
[ 1421473-28-0 ]

Reference： [1]Patent: WO2013/13817,2013,A1
[2]Patent: US2013/29961,2013,A1

26
[ 113293-71-3 ]
[ 1419604-39-9 ]

Reference： [1]Patent: WO2013/13815,2013,A1
[2]Patent: US2013/29962,2013,A1

27
[ 113293-71-3 ]
[ 1419601-14-1 ]

Reference： [1]Patent: WO2013/13815,2013,A1
[2]Patent: US2013/29962,2013,A1

28
[ 113293-71-3 ]
[ 1426136-06-2 ]

Reference： [1]Patent: US2013/59832,2013,A1

29
[ 113293-71-3 ]
[ 1426136-33-5 ]

Reference： [1]Patent: US2013/59832,2013,A1

30
[ 113293-71-3 ]
[ 1426136-32-4 ]

Reference： [1]Patent: US2013/59832,2013,A1

31
potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate [ No CAS ]
[ 113293-71-3 ]
[ 936637-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; sulfuric acid; In ethanol; at 85℃;	To a stirring of <strong>[113293-71-3](6-aminopyridin-3-yl)methanol</strong> (1.24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0 mmol) in EtOH (10 mL) at room temperature was added conc sulfuric acid (10.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C. overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1H NMR (400 MHz, d6-DMSO) delta 9.16 (d, J=6.8 Hz, 1H), 8.26 (s, 1H), 7.67 (s, 1H), 7.19 (dd, J=1.6, 6.8 Hz, 1H), 5.57 (t, J=6.4 Hz, 1H), 4.63 (d, J=6.0, 2H), 4.36 (q, J=7.2 Hz, 2H), 1.35 (t, J=6.8 Hz, 3H). MS m/z 221.1 (M+1)+.
		To a stirring suspension of <strong>[113293-71-3](6-aminopyridin-3-yl)methanol</strong> (1.24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0 mmol) in EtOH (10 mL) at room temperature was added conc sulfuric acid (10.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C. overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1H NMR (400 MHz, d6-DMSO) delta 9.16 (d, J=6.8 Hz, 1H), 8.26 (s, 1H), 7.67 (s, 1H), 7.19 (dd, J=1.6, 6.8 Hz, 1H), 5.57 (t, J=6.4 Hz, 1H), 4.63 (d, J=6.0, 2H), 4.36 (q, J=7.2 Hz, 2H), 1.35 (t, J=6.8 Hz, 3H). MS m/z 221.1 (M+1)+.; To a suspension of ethyl 6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxylate (59) (497.0 mg, 2.26 mmol), DMAP (12.2 mg, 0.1 mmol) and 1H-imidazole (154.0 mg, 2.26 mmol) in dichloromethane (10 mL), was added TIPSCI (523.0 mg, 2.71 mmol). The resulting mixture was stirred overnight at room temperature. The solvent was removed under vacuum to yield crude ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate (60). MS m/z 377.2 (M+1)+.; The crude ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate (60) obtained above was dissolved in THF/MeOH/H2O (3:2:1, 5 mL). 6N LiOH (2.27 mL, 13.6 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. All solvents were removed and 6N HCl was added until pH 5-6. EtOAc (5 mL) was added and the mixture was stirred for 1 hour. The precipitate was filtered and dried to give 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylic acid (61). 1H NMR (400 MHz, d6-DMSO) delta 9.37 (s, 1H), 8.21 (s, 1H), 7.76 (dd, J=1.2, 9.2 Hz, 1H), 7.46 (dd, J=2.0, 9.2 Hz, 1H), 4.94 (s, 2H), 1.20 (m, 3H), 1.08 (d, J=6.8 Hz, 18H). MS m/z 349.2 (M+1)+.
		To a stirring suspension of <strong>[113293-71-3](6-aminopyridin-3-yl)methanol</strong> (1 .24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0mmol) in EtOH (10 mL) at room temperature was added cone sulfuric acid (1 0.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6- (hydroxymethyl)imidazo[1 ,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1 H NMR (400MHz, c/6-DMSO) delta 9.16 (d, J = 6.8 Hz, 1 H), 8.26 (s, 1 H), 7.67 (s, 1 H), 7.19 (dd, J = 1 .6, 6.8 Hz, 1 H), 5.57 (t, J = 6.4 Hz, 1 H), 4.63 (d, J = 6.0, 2H), 4.36 (q, J = 7.2 Hz, 2H), 1 .35 (t, J = 6.8 Hz, 3H). MS m/z 221 .1 (M+1 ) +.

To a stirring suspension of <strong>[113293-71-3](6-aminopyridin-3-yl)methanol</strong> (1 .24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0mmol) in EtOH (10 mL) at room temperature was added cone sulfuric acid (10.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6- (hydroxymethyl)imidazo[1 ,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1 H NMR (400MHz, c/6-DMSO) delta 9.16 (d, J = 6.8 Hz, 1 H), 8.26 (s, 1 H), 7.67 (s, 1 H), 7.19 (dd, J = 1 .6, 6.8 Hz, 1 H), 5.57 (t, J = 6.4 Hz, 1 H), 4.63 (d, J = 6.0, 2H), 4.36 (q, J = 7.2 Hz, 2H), 1 .35 (t, J = 6.8 Hz, 3H). MS m/z 221 .1 (M+1 ) +. To a suspension of ethyl 6-(hydroxymethyl)imidazo[1 ,2-a]pyridine-3-carboxylate (59) (497.0 mg, 2.26 mmol), DMAP (12.2 mg, 0.1 mmol) and 1 H-imidazole (154.0 mg, 2.26 mmol) in dichloromethane (10 mL), was added TIPSCI (523.0 mg, 2.71 mmol). The resulting mixture was stirred overnight at room temperature. The solvent was removed under vacuum to yield crude ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1 ,2-a]pyridine- 3-carboxylate (60). MS m/z 377.2 (M+1 )+. The crude ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1 ,2-a]pyridine-3-carboxylate (60) obtained above was dissolved in THF/MeOH/H20 (3:2:1 , 5 mL). 6N LiOH (2.27 mL, 13.6 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. All solvents were removed and 6N HCI was added until pH 5-6. EtOAc (5 mL) was added and the mixture was stirred for 1 hour. The precipitate was filtered and dried to give 6-(((triisopropylsilyl)oxy)methyl)imidazo[1 ,2-a]pyridine-3-carboxylic acid (61 ). 1 H NMR (400MHz, c/6-DMSO) delta 9.37 (s, 1 H), 8.21 (s, 1 H), 7.76 (dd, J = 1 .2, 9.2 Hz, 1 H), 7.46 (dd, J = 2.0, 9.2 Hz, 1 H), 4.94 (s, 2H), 1 .20 (m, 3H), 1 .08 (d, J = 6.8 Hz, 18H). MS m/z 349.2 (M+1 ) +.

Reference： [1]Patent: US2013/59832,2013,A1 .Location in patent: Paragraph 0476; 0477
[2]Patent: US2013/59846,2013,A1 .Location in patent: Paragraph 0458; 0459; 0460; 0461
[3]Patent: WO2013/33203,2013,A1 .Location in patent: Page/Page column 92-93
[4]Patent: WO2013/33116,2013,A1 .Location in patent: Page/Page column 107; 108

32
[ 113293-71-3 ]
C₁₂H₁₄N₂O₅S [ No CAS ]

Reference： [1]Patent: US2013/59832,2013,A1

33
[ 113293-71-3 ]
[ 1426136-07-3 ]

Reference： [1]Patent: US2013/59832,2013,A1

34
[ 1135-24-6 ]
[ 113293-71-3 ]
(E)-(6-aminopyridin-3-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 48h;	General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 118,p. 299 - 315

35
[ 530-59-6 ]
[ 113293-71-3 ]
(E)-(6-aminopyridin-3-yl)methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 48h;	General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 118,p. 299 - 315

36
[ 113293-71-3 ]
N-(5-((4-ethylpiperazin-1-yl)methyl)pyridin-2-yl)-5-fluoro-4-(3-isopropyl-2-methyl-2H-indazol-5-yl)pyrimidin-2-amine [ No CAS ]

Reference： [1]Patent: US2019/194168,2019,A1

37
[ 113293-71-3 ]
[ 69879-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese(IV) oxide; In dichloromethane; at 50℃; for 16h;	Manganese dioxide (17.51 g) was added to a solution of the compound of formula (a-1) in dichloromethane (30 mL), and the mixture was stirred at 50 C. for 16 hours. TLC (petroleum ether:ethyl acetate=1:1) showed that the reaction was complete. The mixture was cooled to 20 C. and filtered, and the filtrate was concentrated to obtain the compound of formula (a-2) (2.10 g) as a yellow solid. The compound of formula (a-2) was directly used in the next step without purification.

Reference： [1]Patent: US2019/194168,2019,A1 .Location in patent: Paragraph 0149; 0150

38
[ 113293-71-3 ]
[ 1180132-17-5 ]

Reference： [1]Patent: US2019/194168,2019,A1

39
[ 113293-71-3 ]
C₂₇H₃₁FN₈ [ No CAS ]

Reference： [1]Patent: US2019/194168,2019,A1

40
[ 113293-71-3 ]
(E)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(phenyldiazenyl)pyridine [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1341 - 1345

41
[ 113293-71-3 ]
(E)-(6-(phenyldiazenyl)pyridin-3-yl)methanol [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1341 - 1345

42
[ 113293-71-3 ]
C₁₃H₁₃N₃O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1341 - 1345

43
[ 113293-71-3 ]
[ 266358-16-1 ]
C₁₉H₁₅FN₄OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

44
[ 113293-71-3 ]
C₂₀H₁₉FN₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

45
[ 113293-71-3 ]
C₂₁H₂₀FN₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

46
[ 113293-71-3 ]
N-butyl-5-((2-(diethylamino)ethoxy)methyl)pyridin-2-amine [ No CAS ]

Reference： [1]Patent: WO2019/191502,2019,A1

47
[ 113293-71-3 ]
[ 123-72-8 ]
(6-(butylamino)pyridin-3-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; acetonitrile; at 20℃; for 24h;	2-Aminopyridine-5-methanol, 262 (766 mg, 6.17 mmols) and butyraldehyde (445 mg, 6.17 mmmols) were dissolved in 45 ml of anhydrous 1,2-dichloroethane and 20 ml of anhydrous MeCN. Sodium triacetoxyborohydride (1.31 g, 6.17 mmols) was added in one portion, followed by the addition of acetic acid (370 mg, 6.17 mmols). The mixture was stirred at room temperature 24 h. The mixture was diluted with 50 ml of EtOAc and then saturated solution of NaHC03 (60 ml) was added; the mixture was stirred 15 min. Phases were separated, the organic phase was dried over Na2S04, filtered and the solvent evaporated under vacuum. Crude yield, 0.80439 g (72% yield), was consistent with the title compound and was used as is without further purification. 1 H NMR (400 MHz, CDCl3) d 7.98 (d, 7 = 2.0 Hz, 1H), 7.47 (dd, 7 = 8.5, 2.4 Hz, 1H), 6.37 (d, 7 = 8.5 Hz, 1H), 4.53 (m, 3H), 3.24 (td, 7 = 7.1, 5.8 Hz, 2H), 1.64 - 1.54 (m, 2H), 1.42 (dq, 7 = 14.4, 7.3 Hz, 2H), 0.95 (t, 7 = 7.3 Hz, 3H). 13C NMR (101 MHz, CDCl3) d 158.85, 147.69, 137.82, 125.01, 106.38, 63.04, 42.21, 31.75, 20.32, 13.99.

Reference： [1]Patent: WO2019/191502,2019,A1 .Location in patent: Page/Page column 6; 64-65

48
[ 113293-71-3 ]
(2-amino-[1,2,4] triazolo[1,5-a]pyridin-6-yl)methanol [ No CAS ]

Reference： [1]Patent: WO2020/156323,2020,A1

49
[ 113293-71-3 ]
(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methanol [ No CAS ]

Reference： [1]Patent: WO2020/156323,2020,A1

50
[ 113293-71-3 ]
[ 16182-04-0 ]
ethyl N-[[5-(hydroxymethyl)-2-pyridyl]carbamothioyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 50℃; for 3h;	To a solution of (6-aminopyridin-3-yl) methanol (5g) in 1, 4-dioxane (25mL) was added ethyl N- (thioxomethylene) carbamate (7.92 g) . The reaction mixture was stirred at 50 C for 3 hrs. The mixture was concentrated to get a residue. The residue was directly used for the next step.

Reference： [1]Patent: WO2020/156323,2020,A1 .Location in patent: Page/Page column 122

51
[ 10200-59-6 ]
[ 2769-64-4 ]
[ 113293-71-3 ]
(3-(butylamino)-2-(thiazol-2-yl)imidazo[1,2-a]pyridin-6-yl)methanol [ No CAS ]

Reference： [1]Green Chemistry,2021,vol. 23,p. 280 - 287

52
[ 1121-60-4 ]
[ 113293-71-3 ]
[ 78375-48-1 ]
(3-((2-morpholinoethyl)amino)-2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)methanol [ No CAS ]

Reference： [1]Green Chemistry,2021,vol. 23,p. 280 - 287

53
[ 50-00-0 ]
[ 7188-38-7 ]
[ 113293-71-3 ]
(3-(tert-butylamino)imidazo[1,2-a]pyridin-6-yl)methanol [ No CAS ]

Reference： [1]Green Chemistry,2021,vol. 23,p. 280 - 287

54
[ 113293-71-3 ]
N-(3-fluorophenyl)-6-(methoxymethyl)-2-(pyridin-2-yl)imidazo[1,2-a]pyridin-3-amine [ No CAS ]

Reference： [1],

55
[ 113293-71-3 ]
[ 74-88-4 ]
[ 760155-78-0 ]

Reference： [1],

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 113293-71-3 ]

Alcohols

[ 100-55-0 ]

3-Pyridinemethanol

Similarity: 0.85

[ 1027785-19-8 ]

(6-Amino-5-bromopyridin-3-yl)methanol

Similarity: 0.78

[ 23612-57-9 ]

2-Amino-3-hydroxymethylpyridine

Similarity: 0.78

[ 102074-19-1 ]

(5-Methylpyridin-3-yl)methanol

Similarity: 0.77

[ 38070-80-3 ]

Pyridine-3,4-diyldimethanol

Similarity: 0.77

Amines

[ 1603-41-4 ]

2-Amino-5-methylpyridine

Similarity: 0.83

[ 3167-49-5 ]

6-Amino-3-pyridinecarboxylic acid

Similarity: 0.78

[ 1027785-19-8 ]

(6-Amino-5-bromopyridin-3-yl)methanol

Similarity: 0.78

[ 23612-57-9 ]

2-Amino-3-hydroxymethylpyridine

Similarity: 0.78

[ 167837-43-6 ]

(E)-3-(6-Aminopyridin-3-yl)acrylic acid

Similarity: 0.75

Related Parent Nucleus of
[ 113293-71-3 ]

Pyridines

[ 100-55-0 ]

3-Pyridinemethanol

Similarity: 0.85

[ 1603-41-4 ]

2-Amino-5-methylpyridine

Similarity: 0.83

[ 3167-49-5 ]

6-Amino-3-pyridinecarboxylic acid

Similarity: 0.78

[ 1027785-19-8 ]

(6-Amino-5-bromopyridin-3-yl)methanol

Similarity: 0.78

[ 23612-57-9 ]

2-Amino-3-hydroxymethylpyridine

Similarity: 0.78

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 113293-71-3 ] {[proInfo.proName]}

Quality Control of [ 113293-71-3 ]

Related Doc. of [ 113293-71-3 ]

Product Details of [ 113293-71-3 ]

Calculated chemistry of [ 113293-71-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 113293-71-3 ]

Application In Synthesis of [ 113293-71-3 ]

[ 113293-71-3 ] Synthesis Path-Upstream 1~6

[ 113293-71-3 ] Synthesis Path-Downstream 1~55

Related Functional Groups of [ 113293-71-3 ]

Alcohols

Amines

Related Parent Nucleus of [ 113293-71-3 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 113293-71-3 ]

Related Parent Nucleus of
[ 113293-71-3 ]