[ CAS No. 158980-21-3 ] {[proInfo.proName]}

Name: 158980-21-3|Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate|97%
Brand: Ambeed
SKU: A159534
Price: 24.0 USD
Availability: InStock
Rating: 91 (32 reviews)

,{[proInfo.pro_purity]}

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

2D 3D

Structure of 158980-21-3 * 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 [ 158980-21-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 158980-21-3 ]

SDS Specification

Alternatived Products of [ 158980-21-3 ]

Product Details of [ 158980-21-3 ]

CAS No. :	158980-21-3	MDL No. :	MFCD05864804
Formula :	C₁₀H₁₁N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PKWHXLCNUIXDIK-UHFFFAOYSA-N
M.W :	205.21	Pubchem ID :	14925628
Synonyms :

Calculated chemistry of [ 158980-21-3 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	55.68
TPSA :	69.62 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	1.63
Log Po/w (WLOGP) :	1.1
Log Po/w (MLOGP) :	0.37
Log Po/w (SILICOS-IT) :	0.37
Consensus Log Po/w :	1.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.39
Solubility :	0.845 mg/ml ; 0.00412 mol/l
Class :	Soluble
Log S (Ali) :	-2.7
Solubility :	0.405 mg/ml ; 0.00197 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.21
Solubility :	1.25 mg/ml ; 0.00611 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.09

Safety of [ 158980-21-3 ]

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 [ 158980-21-3 ]

* 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 [ 158980-21-3 ]
Downstream synthetic route of [ 158980-21-3 ]

[ 158980-21-3 ] Synthesis Path-Upstream 1~3

1
[ 38923-08-9 ]
[ 158980-21-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 5 h;	A solution of 250mg (1.01 mmol) of ethyl 6-ni-troimidazo[ 1 ,2-a]pyridine-2-carboxylate in 20 ml of ethanolwas hydrogenated in the presence of 30 mg of palladium(10percent on activated carbon) at RT and standard pressure for5 h. The reaction mixture was then filtered through Celiteand the residue was washed with ethanol. The combinedfiltrates were concentrated under reduced pressure and dried.Yield: 215 mg (quant.)10502] LC/MS [Method 5]: R=1.40 mm; MS (ESIpos):mlz=206 (M+H),10503] ‘H-NMR (400 MHz, DMSO-d5): ö [ppm]=8.33 (s,1H), 7.66 (s, 1H), 7.37 (d, 1H), 6.94 (dd, 1H), 5.11 (s, 2H),4.26 (q, 2H), 1.29 (t, 3H).
68%	With hydrogenchloride; zinc In methanol; water at 0℃; for 0.5 h;	A suspension of ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate (20) (20 g, 85 mmol) in MeOH (200 ml) was cooled to 0 °C, 12M hydrogen chloride (70 ml, 850 mmol) was added drop wise followed by portion wise addition of zinc (22.3 g, 340 mmol). The reaction mixture was stirred for 30 minutes.Next, MeOH (140 ml) was added and the reaction was quenched with concentrated NH3(15 equiv.) and filtered. The solid residue was washed with MeOH (2 x 25 ml). The filtratewas concentrated and re-suspended in CHC13 (700 ml), H20 (300 ml) and concentrated NH3(300 ml, 35percent solution). This mixture was stirred until everything was dissolved. The layerswere separated and the water layer was extracted once with CHC13. The organic layers werecombined, washed with a saturated aqueous NaC1 solution (50 ml), dried over MgSO4,filtered and concentrated in vacuo to yield ethyl 6-aminoimidazo [1 ,2-a]pyridine-2-carboxylate (21) (11.8 g, 68percent) as a grey/green solid. UPLC-MS confirmed that the desired product was obtained.
48%	With hydrogen In ethanol at 20℃; for 18 h;	Ethyl 6-nitroimidazo[l,2-α]pyridine-2-carboxylate (1.137 g, 4.83 mmol) and 10percent Pd on C (200 mg) were suspended in EtOH (4 mL). The reaction mixture was stirred at room temperature under 1 atm of hydrogen for 18 h. It was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography to afford ethyl 6-aminoimidazo[l ,2-α]pyridine-2-carboxylate as a green solid (478 mg, yield: 48percent). ¹H NMR (400 MHz, CDCl₃): δ: 8.026 ( I H, s), 7.571 (2H, m), 6.91 1 (1 H, dd, J = 9.6 Hz, J₂ = 2.0 Hz), 4.475 (2H, q, J = 7.2 Hz), 1 .438 (3H, t, J = 7.2 Hz).

Reference： [1] Patent: US2016/272637, 2016, A1, . Location in patent: Paragraph 0500; 0501; 0502; 0503
[2] Heterocycles, 1994, vol. 38, # 7, p. 1527 - 1532
[3] Molecular Pharmaceutics, 2015, vol. 12, # 6, p. 1813 - 1835
[4] Patent: WO2015/185142, 2015, A1, . Location in patent: Page/Page column 20; 21
[5] Patent: WO2008/100423, 2008, A1, . Location in patent: Page/Page column 111
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4589 - 4593
[7] Patent: WO2010/62171, 2010, A2, . Location in patent: Page/Page column 152

2
[ 70-23-5 ]
[ 158980-21-3 ]

Reference： [1] Molecular Pharmaceutics, 2015, vol. 12, # 6, p. 1813 - 1835
[2] Patent: WO2015/185142, 2015, A1,
[3] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 5, p. 1101 - 1111

3
[ 4214-76-0 ]
[ 158980-21-3 ]

Reference： [1] Molecular Pharmaceutics, 2015, vol. 12, # 6, p. 1813 - 1835
[2] Patent: WO2015/185142, 2015, A1,
[3] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 5, p. 1101 - 1111

[ 158980-21-3 ] Synthesis Path-Downstream 1~45

1
[ 38923-08-9 ]
[ 158980-21-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; under 760.051 Torr; for 5h;	A solution of 250mg (1.01 mmol) of ethyl 6-ni-troimidazo[ 1 ,2-a]pyridine-2-carboxylate in 20 ml of ethanolwas hydrogenated in the presence of 30 mg of palladium(10% on activated carbon) at RT and standard pressure for5 h. The reaction mixture was then filtered through Celiteand the residue was washed with ethanol. The combinedfiltrates were concentrated under reduced pressure and dried.Yield: 215 mg (quant.)10502] LC/MS [Method 5]: R=1.40 mm; MS (ESIpos):mlz=206 (M+H),10503] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=8.33 (s,1H), 7.66 (s, 1H), 7.37 (d, 1H), 6.94 (dd, 1H), 5.11 (s, 2H),4.26 (q, 2H), 1.29 (t, 3H).
70%	With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 4h;	To a stirred solution of ethyl 6-nitroimidazo[l,2-a]pyridine-2-carboxylate (A34, 7.30 g, 31.73 mmol) in methanol(lOOmL) was added Pd/C(1.6 g, 15.86 mmol) under N2 atmosphere and the reaction mixture was stirred under H2 ballon pressure at room temperature for 4h. after completion of reaction mixture filtered through celite bed and washed with EtOAc. The filtrate was concentrated to dryness. The residue was washed with n-pentane dried to get compound ethyl 6-aminoimidazo[l,2-a]pyridine-2-carboxylate A35 as a green solid. Yield: 4.50 g(70%) LC-MS(ES) m/z : 205.99[M+H]+.
68%	With hydrogenchloride; zinc; In methanol; water; at 0℃; for 0.5h;	A suspension of ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate (20) (20 g, 85 mmol) in MeOH (200 ml) was cooled to 0 C, 12M hydrogen chloride (70 ml, 850 mmol) was added drop wise followed by portion wise addition of zinc (22.3 g, 340 mmol). The reaction mixture was stirred for 30 minutes.Next, MeOH (140 ml) was added and the reaction was quenched with concentrated NH3(15 equiv.) and filtered. The solid residue was washed with MeOH (2 x 25 ml). The filtratewas concentrated and re-suspended in CHC13 (700 ml), H20 (300 ml) and concentrated NH3(300 ml, 35% solution). This mixture was stirred until everything was dissolved. The layerswere separated and the water layer was extracted once with CHC13. The organic layers werecombined, washed with a saturated aqueous NaC1 solution (50 ml), dried over MgSO4,filtered and concentrated in vacuo to yield ethyl 6-aminoimidazo [1 ,2-a]pyridine-2-carboxylate (21) (11.8 g, 68%) as a grey/green solid. UPLC-MS confirmed that the desired product was obtained.

48%

With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 760.051 Torr; for 18h;

Ethyl 6-nitroimidazo[l,2-alpha]pyridine-2-carboxylate (1.137 g, 4.83 mmol) and 10% Pd on C (200 mg) were suspended in EtOH (4 mL). The reaction mixture was stirred at room temperature under 1 atm of hydrogen for 18 h. It was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography to afford ethyl 6-aminoimidazo[l ,2-alpha]pyridine-2-carboxylate as a green solid (478 mg, yield: 48%). 1H NMR (400 MHz, CDCl3): delta: 8.026 ( I H, s), 7.571 (2H, m), 6.91 1 (1 H, dd, J = 9.6 Hz, J2 = 2.0 Hz), 4.475 (2H, q, J = 7.2 Hz), 1 .438 (3H, t, J = 7.2 Hz).

Reference： [1]Patent: US2016/272637,2016,A1 .Location in patent: Paragraph 0500; 0501; 0502; 0503
[2]Heterocycles,1994,vol. 38,p. 1527 - 1532
[3]Patent: WO2019/102494,2019,A1 .Location in patent: Paragraph 000183
[4]Molecular Pharmaceutics,2015,vol. 12,p. 1813 - 1835
[5]Patent: WO2015/185142,2015,A1 .Location in patent: Page/Page column 20; 21
[6]Patent: WO2008/100423,2008,A1 .Location in patent: Page/Page column 111
[7]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4589 - 4593
[8]Patent: WO2010/62171,2010,A2 .Location in patent: Page/Page column 152

2
[ 87-13-8 ]
[ 158980-21-3 ]
ethyl N-(2-ethoxycarbonylimidazo[1,2-a]pyridin-6-yl)aminomethylenemalonate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 6576 - 6584

3
[ 158980-21-3 ]
ethyl 8-ethoxycarbonyl-6,9-dihydro-9-oxoimidazo[1,2-a][1,5]naphthyridine-2-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 6576 - 6584

4
[ 158980-21-3 ]
C₂₆H₂₆N₆O₇ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 6576 - 6584

5
4′-(tert butyl)-[1,1′-biphenyl]-2-carboxylic acid [ No CAS ]
[ 158980-21-3 ]
[ 1048367-56-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h;	A mixture containing 4'-/er/-butylbiphenyl-2-carboxylic acid (539 mg, 2.12 mmol), ethyl 6-aminoimidazo[l ,2-alpha]pyridine-2-carboxylate (478 mg, 2.33 mmol), DMAP (295 mg, 2.42 mmol) and EDC HCl (61 1 mg, 3.18 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 18 h. The reaction mixture was diluted with saturated aqueous NaHCO3 solution. The aqueous layer was separated and further extracted with CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (elution: petroleum ether/EtOAc = 1 :2 plus 5% CH2Cl2) to give ethyl 6-(4'-tert-butylbiphenyl-2- ylcarboxamido)imidazo[l ,2-alpha]pyridine-2-carboxylate as a green solid (652 mg, yield: 70%). 1H NMR (400 MHz, CDCl3): delta: 9.1 16 (IH, s), 8.141 (IH, s), 7.982 (IH, dd, J= 7.6 Hz), 7.379-7.621 (8H, m), 6.799 (IH, s), 5.965 (IH, dd, J1 = 9.6 Hz, J2 = 2.0 Hz), 4.483 (2H, q, J = 7.2 Hz), 1.442 (3H, t, J = 7.2 Hz), 1.368 (9H, s).

Reference： [1]Patent: WO2008/100423,2008,A1 .Location in patent: Page/Page column 111-112

6
[ 158980-21-3 ]
[ 195457-71-7 ]
[ 845827-07-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4589 - 4593

7
[ 108-24-7 ]
[ 158980-21-3 ]
ethyl 6-acetamidoimidazo[1,2-a]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 17 6-Acetamido-N-phenylimidazo[1,2-a]pyridine-2-carboxamide 17.1 Ethyl 6-acetamidoimidazo[1,2-a]pyridine-2-carboxylate A suspension of 0.2 g of <strong>[158980-21-3]ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate</strong> (Heterocycles, 38(7), 1527 (1994)) in 1 ml of acetic anhydride is heated at reflux for 45 minutes. The reaction mixture is concentrated under reduced pressure; the residue is taken up in water and basified by addition of a 1N sodium hydroxide solution. The solid is filtered off and dried to give 150 mg of ethyl 6-acetamidoimidazo[1,2-a]pyridine-2-carboxylate in the form of an ecru solid. 1H NMR spectrum (d6-DMSO, 6 in ppm): 1.31 (t, J=7.0 Hz, 3H); 2.09 (s, 3H); 4.30 (q, J=7.0 Hz, 2H); 7.24 (dd, J=1.5 and 9.5 Hz, 1H); 7.59 (d, J=9.5 Hz, 1H); 8,60 (s, 1H); 9.23 (broad s, 1H); 10.1 (s, 1H). Mass spectrum (EI): m/z=246 [M-H]-, m/z=248 [M+H]+.

Reference： [1]Patent: US2009/149441,2009,A1 .Location in patent: Page/Page column 7

8
[ 24424-99-5 ]
[ 158980-21-3 ]
C₁₅H₁₉N₃O₄ [ No CAS ]

Reference： [1]Patent: WO2010/62171,2010,A2 .Location in patent: Page/Page column 152

9
[ 4637-24-5 ]
[ 158980-21-3 ]
[ 1168040-75-2 ]

Yield	Reaction Conditions	Operation in experiment
	for 2h;Reflux;	EXAMPLE 7; 6-[(1E)-(Dimethylamino)methylene]amino}-N-phenylimidazo[1,2-a]pyridine-2-carboxamide7.1: Ethyl 6-[(1E)-(dimethylamino)methylene]amino}-5-methylimidazo[1,2-a]pyridine-2-carboxylate200 mg of <strong>[158980-21-3]ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate</strong> (Heterocycles 38(7), 1527 (1994)) are treated with 2 mL of N,N-dimethylformamide dimethyl acetal. The reaction mixture is refluxed for 2 hours and then cooled and diluted with pentane. The precipitate is filtered off by suction, washed and dried to give 180 mg of ethyl 6-[(1E)-(dimethylamino)methylene]amino}-5-methylimidazo[1,2-a]pyridine-2-carboxylate in the form of an ochre-coloured solid.1H NMR spectrum (DMSO-d6, delta in ppm): 1.31 (t, J=3H), 2.91 (broad s, 3H), 3.02 (broad s, 3H), 4.29 (q, J=7.0 Hz, 2H), 7.21 (dd, J=1.5 and 9.5 Hz, 1H), 7.47 (d, J=9.5 Hz, 1H), 7.84 (s, 1H), 8.05 (d, J=1.5 Hz, 1H), 8.35 (s, 1H).Mass spectrum (LC-MS-DAD-ELSD): m/z 261 [M+H]+, m/z 233 [MH-C2H5]+

Reference： [1]Patent: US2010/317620,2010,A1 .Location in patent: Page/Page column 5

10
[ 158980-21-3 ]
[ 79-44-7 ]
[ 1403333-30-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃;	a) Ethyl 6-(3,3-dimethylureido)imidazo[l ,2-a]pyridine-2-carboxylateEthyl 6-aminoimidazo[l,2-a]pyridine-2-carboxylate (0.975 mmol, 0.2 g) was dissolved in THF (10 ml). Triethylamine (2.92 mmol, 0.296 g) was added and the reaction mixture was cooled to 0 C. Dimethylcarbamyl chloride (1.462 mmol, 0.135 ml) was added carefully and the mixture was allowed to warm to ambient temperature with stirring. More of dimethylcarbamyl chloride (1.462 mmol, 0.135 ml) was added and the stirring continued for another hour. The solvent was evaporated, DCM was added and the resulting mixture was washed with NaHC03 solution and water. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.066 g of the title compound was obtained. -NMR (400 MHz, DMSO-<½): delta 1.31 (t, 3H), 2.95 (s, 6H), 4.29 (q, 2H), 7.39.7.44 (M, IH), 7.50-7.54 (m, 1H), 8.41 (s, 1H), 8.54 (s, 1H), 8.89-8.93 (m, 1H).

Reference： [1]Patent: WO2012/143599,2012,A1 .Location in patent: Page/Page column 49

11
[ 124-63-0 ]
[ 158980-21-3 ]
[ 1403333-36-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃;	a) Ethyl 6-(N-(methylsulfonyl)methylsulfonamido)imidazo[l ,2-a]pyridine-2- carboxylateEthyl 6-aminoimidazo[l,2-a]pyridine-2-carboxylate (0.975 mmol, 0.2 g) was dissolved in THF (10 ml). Triethylamine (9.75 mmol, 0.986 g) was added and the mixture was cooled to 0 C. Methanesulfonyl chloride (9.75 mmol, 1.116 g) was slowly added and the mixture was allowed to cool to RT. The stirring continued at RT until the reaction was finished. The solvent was evaporated, DCM was added and washed with NaHC03 solution and water. The organic phase was dried, filtered and evaporated. The crude product was purified with flash chromatography. 0.149 g of the title compound was obtained. -NMR (400 MHz, DMSO-i 6): delta 1.33 (t, 3H), 3.61 (s, 6H), 4.34 (q, 2H), 7.50 (dd, 1H), 7.69-7.74 (m, 1H), 8.54-8.56 (m, 1H), 9.00- 9.02 (m, 1H).

Reference： [1]Patent: WO2012/143599,2012,A1 .Location in patent: Page/Page column 50

12
[ 158980-21-3 ]
[ 1403333-32-3 ]

Reference： [1]Patent: WO2012/143599,2012,A1
[2]Patent: US2014/94474,2014,A1

13
[ 158980-21-3 ]
[ 1403333-38-9 ]

Reference： [1]Patent: WO2012/143599,2012,A1

14
[ 158980-21-3 ]
[ 1403333-28-7 ]

Reference： [1]Patent: US2014/94474,2014,A1

15
[ 96042-30-7 ]
[ 158980-21-3 ]
[ 79-44-7 ]
[ 1403333-30-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran;	a) Ethyl 6-(3,3-dimethylureido)imidazo[1,2-a]pyridine-2-carboxylate <strong>[158980-21-3]Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate</strong> (0.975 mmol, 0.2 g) was dissolved in THF (10 ml). Triethylamine (2.92 mmol, 0.296 g) was added and the reaction mixture was cooled to 0 C. Dimethylcarbamyl chloride (1.462 mmol, 0.135 ml) was added carefully and the mixture was allowed to warm to ambient temperature with stirring. More of dimethylcarbamyl chloride (1.462 mmol, 0.135 ml) was added and the stirring continued for another hour. The solvent was evaporated, DCM was added and the resulting mixture was washed with NaHCO3 solution and water. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.066 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): delta 1.31 (t, 3H), 2.95 (s, 6H), 4.29 (q, 2H), 7.39-7.44 (m, 1H), 7.50-7.54 (m, 1H), 8.41 (s, 1H), 8.54 (s, 1H), 8.89-8.93 (m, 1H).

Reference： [1]Patent: US2014/94474,2014,A1 .Location in patent: Page/Page column

16
[ 96042-30-7 ]
[ 124-63-0 ]
[ 158980-21-3 ]
Ethyl 6-(N-(methylsulfonyl)methylsulfonamido)imidazo[1,2-a]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran;	a) Ethyl 6-(N-(methylsulfonyl)methylsulfonamido)imidazo[1,2-a]pyridine-2-carboxylate <strong>[158980-21-3]Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate</strong> (0.975 mmol, 0.2 g) was dissolved in THF (10 ml). Triethylamine (9.75 mmol, 0.986 g) was added and the mixture was cooled to 0 C. Methanesulfonyl chloride (9.75 mmol, 1.116 g) was slowly added and the mixture was allowed to cool to RT. The stirring continued at RT until the reaction was finished. The solvent was evaporated, DCM was added and washed with NaHCO3 solution and water. The organic phase was dried, filtered and evaporated. The crude product was purified with flash chromatography. 0.149 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): delta 1.33 (t, 3H), 3.61 (s, 6H), 4.34 (q, 2H), 7.50 (dd, 1H), 7.69-7.74 (m, 1H), 8.54-8.56 (m, 1H), 9.00-9.02 (m, 1H).

Reference： [1]Patent: US2014/94474,2014,A1 .Location in patent: Page/Page column

17
[ 70-23-5 ]
[ 158980-21-3 ]

Reference： [1]Molecular Pharmaceutics,2015,vol. 12,p. 1813 - 1835
[2]Patent: WO2015/185142,2015,A1
[3]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 1101 - 1111
[4]Patent: WO2019/102494,2019,A1

18
[ 4214-76-0 ]
[ 158980-21-3 ]

19
[ 158980-21-3 ]
6-(4-(methoxymethoxy)benzamido)imidazo[1,2-a]-pyridine-2-carboxylic acid [ No CAS ]

Reference： [1]Molecular Pharmaceutics,2015,vol. 12,p. 1813 - 1835
[2]Patent: WO2015/185142,2015,A1

20
[ 158980-21-3 ]
(S)-N-(2-(5-(benzyloxy)-1-(chloromethyl)-9-methyl-2,3-dihydro-1H-benzo[e]indole-3-carbonyl)imidazo[1,2-a]pyridin-6-yl)-4-(methoxymethoxy)benzamide [ No CAS ]

Reference： [1]Molecular Pharmaceutics,2015,vol. 12,p. 1813 - 1835
[2]Patent: WO2015/185142,2015,A1

21
[ 158980-21-3 ]
[ 1345681-72-2 ]

Reference： [1]Molecular Pharmaceutics,2015,vol. 12,p. 1813 - 1835
[2]Patent: WO2015/185142,2015,A1

22
[ 158980-21-3 ]
C₂₉H₂₃ClN₄O₄*ClH [ No CAS ]