[ CAS No. 24484-98-8 ] {[proInfo.proName]}

Name: 24484-98-8|4-Chloropyridine-2,3-diamine|97%
Brand: Ambeed
SKU: A115518
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Quality Control of [ 24484-98-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 24484-98-8 ]

Product Details of [ 24484-98-8 ]

CAS No. :	24484-98-8	MDL No. :	MFCD13181777
Formula :	C₅H₆ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	APGDUAJEMRMIJU-UHFFFAOYSA-N
M.W :	143.57	Pubchem ID :	22418004
Synonyms :

Calculated chemistry of [ 24484-98-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	38.06
TPSA :	64.93 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) :	-6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.9
Log Po/w (XLOGP3) :	0.45
Log Po/w (WLOGP) :	0.92
Log Po/w (MLOGP) :	0.19
Log Po/w (SILICOS-IT) :	0.63
Consensus Log Po/w :	0.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.51
Solubility :	4.47 mg/ml ; 0.0311 mol/l
Class :	Very soluble
Log S (Ali) :	-1.38
Solubility :	5.96 mg/ml ; 0.0415 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.9
Solubility :	1.81 mg/ml ; 0.0126 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 24484-98-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 24484-98-8 ]

* 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 [ 24484-98-8 ]
Downstream synthetic route of [ 24484-98-8 ]

[ 24484-98-8 ] Synthesis Path-Upstream 1~4

1
[ 24484-98-8 ]
[ 122-51-0 ]
[ 6980-11-6 ]

Reference： [1] Patent: WO2017/87905, 2017, A1, . Location in patent: Page/Page column 201

2
[ 6980-08-1 ]
[ 24484-98-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With iron; ammonium chloride In propan-1-ol; water at 70℃; for 2 h;	4-Chloropyridine-2,3-diamine In a 100-mL round bottom flask, 4-chloro-3-nitropyridin-2-amine (2 g, 11.52 mmol, 1.00 equiv) was dissolved in propanol (20 mL) and water (10 mL), to which was added Fe powder (3.23 g, 57.84 mmol, 5.02 equiv) and NH₄Cl (3.06 g, 57.21 mmol, 4.96 equiv) in sequence at room temperature. The resulting mixture was stirred for 2 h at 70° C. After the reaction was done, the reaction mixture was cooled to room temperature and filtered through a Celite pad. The filtrate was concentrated under reduced pressure to afford 4-chloropyridine-2,3-diamine (1.6 g, 97percent) as black solid.
96%	With iron; ammonium chloride In water; isopropyl alcohol at 70℃; for 2 h;	a) 4-Chloropyridine-2,3-diamine (A 15) Iron powder (1.126 g, 20.17 mmol) followed by NH₄CI (1.079 g, 20.17 mmol) were added to a stirred suspension of 2-amino-4-chloro-3-nitropyridine A14 (0.700 g, 4.03 mmol) in /-PrOH (30 ml_) and water (15 ml_) at room temperature. The reaction was heated to 70 °C and stirred at this temperature for 2 hours. The reaction was cooled and filtered through a plug of celite which was washed with EtOAc (150 ml_). The filtrate was washed with saturated aqueous NaHC0₃ (100 ml_), brine (100 ml_), dried (Na₂S0₄), filtered and concentrated in vacuo to give the title compound (0.555 g, 96percent) as a brown solid. LCMS-A rt 1.34 min, m/z (positive ion) 144.1 , 146.2 [M+H]⁺.

Reference： [1] Patent: US2016/96834, 2016, A1, . Location in patent: Paragraph 0322
[2] Patent: WO2014/128465, 2014, A1, . Location in patent: Page/Page column 54; 55
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6567 - 6571
[4] Patent: US5298518, 1994, A,
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4344 - 4353
[6] Patent: WO2008/144253, 2008, A1, . Location in patent: Page/Page column 60-61

3
[ 19798-80-2 ]
[ 24484-98-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4344 - 4353
[2] Patent: US2016/96834, 2016, A1,

4
[ 64-19-7 ]
[ 24484-98-8 ]
[ 1086423-62-2 ]

Reference： [1] Patent: WO2008/144253, 2008, A1, . Location in patent: Page/Page column 60-61

[ 24484-98-8 ] Synthesis Path-Downstream 1~61

1
[ 24484-98-8 ]
[ 26271-13-6 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1970,vol. 89,p. 5 - 10

2
[ 24484-98-8 ]
[ 26271-15-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1970,vol. 89,p. 5 - 10

3
[ 24484-98-8 ]
[ 26271-16-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1970,vol. 89,p. 5 - 10

4
[ 24484-98-8 ]
[ 100-10-7 ]
4-(7-chloro-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6567 - 6571

5
[ 6980-08-1 ]
[ 24484-98-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With iron; ammonium chloride; In propan-1-ol; water; at 70℃; for 2.0h;	4-Chloropyridine-2,3-diamine In a 100-mL round bottom flask, 4-chloro-3-nitropyridin-2-amine (2 g, 11.52 mmol, 1.00 equiv) was dissolved in propanol (20 mL) and water (10 mL), to which was added Fe powder (3.23 g, 57.84 mmol, 5.02 equiv) and NH4Cl (3.06 g, 57.21 mmol, 4.96 equiv) in sequence at room temperature. The resulting mixture was stirred for 2 h at 70 C. After the reaction was done, the reaction mixture was cooled to room temperature and filtered through a Celite pad. The filtrate was concentrated under reduced pressure to afford 4-chloropyridine-2,3-diamine (1.6 g, 97%) as black solid.
96%	With iron; ammonium chloride; In water; isopropyl alcohol; at 70℃; for 2.0h;	a) 4-Chloropyridine-2,3-diamine (A 15) Iron powder (1.126 g, 20.17 mmol) followed by NH4CI (1.079 g, 20.17 mmol) were added to a stirred suspension of 2-amino-4-chloro-3-nitropyridine A14 (0.700 g, 4.03 mmol) in /-PrOH (30 ml_) and water (15 ml_) at room temperature. The reaction was heated to 70 C and stirred at this temperature for 2 hours. The reaction was cooled and filtered through a plug of celite which was washed with EtOAc (150 ml_). The filtrate was washed with saturated aqueous NaHC03 (100 ml_), brine (100 ml_), dried (Na2S04), filtered and concentrated in vacuo to give the title compound (0.555 g, 96%) as a brown solid. LCMS-A rt 1.34 min, m/z (positive ion) 144.1 , 146.2 [M+H]+.
	With hydrogenchloride; iron; In methanol;	(1) 4-Chloro-2,3-diaminopyridine STR116 3.6 g of 2-amino-4-chloro-3-nitropyridine was added to 21 ml of methanol and 24 ml of concentrated hydrochloric acid, and the mixture was vigorously stirred. Powdery iron was added in small portions to the mixture. 10 min after the completion of the addition, the mixture was poured into an iced concentrated aqueous ammonia and extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was distilled off in vacuo. The residue was purified by silica gel chromatography (CH2 Cl2:MeOH=20:1?10:1) to prepare 2.6 g of 4-chloro-2,3-diaminopyridine as a purplish white crystal. NMR(90 MHz, CDCl3, delta value): 7.20(d,1H,J=5 Hz),6.48(d,1H,J=5 Hz),5.74 (bs,2H),4.87(bs,2H).

With hydrogenchloride; tin(ll) chloride; In ethanol; water; at 75℃;

Intermediate 7 (2.31 g, 13.31 mmol) is suspended in EtOH (20.OmL), to which is added a solution of SnCl2 (6.31 g, 33.27 mmol) in HCl (con. 6.0 mL), and the reaction mixture is heated at 75C for half h. The solution is diluted with ethyl acetate (250 mL), washed with K2CO3 solution and brine, dried and evaporated to give crude 4-chloropyridine-2,3-diamine (8), which is <n="62"/>P A T E N TGNF Docket No.: P1267PC10 used without purification. 1H NMR 400 MHz (CDCl3) delta 7.26 (d, J= 5.4 Hz, IH), 6.55 (d, J= 5.4 Hz, IH), 5.86 (s, 2H), 4.97 (s, 2H); MS m/z 144.00 (M + 1).

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0322
[2]Patent: WO2014/128465,2014,A1 .Location in patent: Page/Page column 54; 55
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6567 - 6571
[4]Patent: US5298518,1994,A
[5]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4344 - 4353
[6]Patent: WO2008/144253,2008,A1 .Location in patent: Page/Page column 60-61

6
[ 884004-52-8 ]
[ 24484-98-8 ]
[ 884004-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In ethanol; at 20℃; for 18.0h;	K. 6-(8-(Quinoxalin-2-ylammo)pyrido[2,3-blpgammarazin-3-yl)-5-ftrifluoromethyl)nicotinamide (compound 14) 1. 6-(8-Chloropyrido[2,3-b]pyrazin-3-yl)-5-(trifluoromethyl)nicotinamideDissolve 6-(2,2-dihydroxyacetyl)-5-(trifluoromethyl)nicotinamide (8.0 g) in 100.0 mL of EtOH and then add <strong>[24484-98-8]4-chloro-2,3-diaminopyridine</strong> (800 mg) followed by addition Of NaHCO3 (3.6 g). Stir the reaction at room temperature for 18 hours under N2 atmosphere. Concentrate the reaction mixture under vacuum, and purify by column chromatography to afford the title product as a yellow solid.

Reference： [1]Patent: WO2006/42289,2006,A2 .Location in patent: Page/Page column 64

7
3-fluoro-4-(morpholin-4-ylmethyl)benzoic acid hydrochloride [ No CAS ]
[ 24484-98-8 ]
7-chloro-2-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With trichlorophosphate; at 150℃; for 0.5h;Microwave irradiation;	General Method EE5 a-i2,3-Diamino-4-chloropyridine El (prepared according to EP0420237) (143 mg, 1.0 mmol) and the amino acid E2a-i (1.0-1.1 mmol) were dissolved in POCl3 (15 mL) in a20 mL microwave vial. The reaction mixture was stirred at +1500C for 30 min in a microwave reactor. After cooling down, the solvent was removed under vacuum. A saturated solution OfNaHCO3 was added and this solution was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and evaporated under vacuum to afford E3a-i as a crude product.General procedure for amidation :The imidazopyridine E3a-i (1.0 equiv.) was suspended in THF and IN HCl in ether was added slowly. The solvents were removed in vacuo and the resulting salt was dried at +60 0C in vacuo. The salt was mixed with NaI (10 equiv.) and MeCN was added. The reaction mixture was stirred at +160 C for 10 minutes in a microwave reactor. After cooling to r.t, the mixture was poured onto a solution OfNa2S2O3 (10%) and saturated NaHCO3 (aq.). The product was extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to afford the iodoimidazopyridine E4a-i as a crude product. This iodoimidazopyridine E4a-i (1.0 equiv.) was mixed with 3-methoxypropylamine (4.0 equiv.), DBU (3.0 equiv.), imidazole (0.5 equiv.) Mo(CO)6 (1.0 equiv) and Pd(dppf)Cl2 (0.1 equiv.) in THF. The reaction mixture was heated at +150 C for 15 EPO <DP n="33"/>minutes in a microwave reactor. After cooling to r.t. the solvent was evaporated in vacuo. The crude product was diluted in MeOH and pre-purified with a SCX column (ion exchange resin), followed by purification by preparative HPLC. After extraction with EtOAc, drying (Na2SO4) and filtration the solvent was evaporated in vacuo to afford a solid. This solid was dissolved in THF and IN HCl in ether was added. The title compound E5 a-i was afforded after evaporation of the solvent in vacuo.; Example 8(b) 7- Chloro-2-[3-fluoro-4- (morpholin-4-yhnethyl)phenyl]-3H- imidazo[4, 5-b] pyridineThe title compound was prepared in accordance with the general method E using 3- fluoro-4-(morpholin-4-ylmethyl)benzoic acid hydrochloride (obtained from Example8(a)) (302 mg, 1.1 mmol), giving 220 mg (63% yield) of the title compound. MS (ESI) m/z 347 (M +1).

Reference： [1]Patent: WO2007/40439,2007,A1 .Location in patent: Page/Page column 31-32; 43

8
[ 64-19-7 ]
[ 24484-98-8 ]
[ 1086423-62-2 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 8 (700mg, 4.876 mmol), polyphosphoric acid (5 g) and HOAc (442 mg, 7.31 mmol) are heated at 1500C for one hour. The reaction is dissolved in water, then NaOH is added until the pH is adjusted to pH=13. The solution is extracted with ethyl acetate (2x150 mL), washed with K2CO3 solution and brine, dried, and evaporated to give crude 7-chloro-2-methyl- 3H-imidazo[4,5-b]pyridine (9), which is used without purification. 1H NMR 400 MHz (CDCl3) delta 8.14 (s, IH), 6.55 (m, 2H), 2.69 (s, 3H); MS m/z 168.00 (M + 1).

Reference： [1]Patent: WO2008/144253,2008,A1 .Location in patent: Page/Page column 60-61

9
[ 131543-46-9 ]
[ 24484-98-8 ]
8-chloropyrido[2,3-b]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In tetrahydrofuran; at 20℃; for 6.0h;	To a solution of <strong>[24484-98-8]4-chloropyridine-2,3-diamine</strong> (1.90 g, 13.20 minol) in THF (100 mL) was added oxaldehyde (1.00 g, 17.20 minol) at room temperature. The resulting solution was then stirred for 6 h at room temperature. When the reaction was done, the reactionminxture was concentrated under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in petroleum ether (0% to 50% gradient) to yield 8-chloropyrido[2,3-bjpyrazine as yellow solid (2.10 g, 91%). MS: m/z = 166.1 [M+Hj.
91%	In tetrahydrofuran; at 20℃; for 6.0h;Inert atmosphere;	To a solution of <strong>[24484-98-8]4-chloropyridine-2,3-diamine</strong> (1.90 g, 13.20 mmol) in THF (100 mL) was added oxaldehyde (1.00 g, 17.20 mmol) at room temperature. The resulting solution was then stirred for 6 h at room temperature. When the reaction was done, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in petroleum ether (0% to 50% gradient) to yield 8-chloropyrido[2,3-b]pyrazine as yellow solid (2.10 g, 91%). MS: m/z=166.1 [M+H]+.

Reference： [1]Patent: WO2017/106607,2017,A1 .Location in patent: Paragraph 00201; 00202
[2]Patent: US2019/23687,2019,A1 .Location in patent: Paragraph 0216; 0231; 0232
[3]Patent: US2013/310391,2013,A1 .Location in patent: Paragraph 0332

10
[ 7304-32-7 ]
[ 24484-98-8 ]
[ 1533399-37-9 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 828 - 835

11
[ 24484-98-8 ]
C₁₂H₈ClFN₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 828 - 835

12
[ 24484-98-8 ]
[ 1533399-01-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 828 - 835

13
[ 4397-53-9 ]
[ 24484-98-8 ]
2-(4-(benzyloxy)phenyl)-7-chloro-3H-imidazo[4,5-b]pyridine [ No CAS ]

Reference： [1]Patent: WO2014/128465,2014,A1

14
[ 4397-53-9 ]
[ 24484-98-8 ]
(E)-N<SUP>3</SUP>-(4-(benzyloxy)benzylidene)-4-chloropyridine-2,3-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	In water; for 22.0h;Reflux;	b) (E)-N3-(4-(Benzyloxy)benzylidene)-<strong>[24484-98-8]4-chloropyridine-2,3-diamine</strong> (A 16) 4-Chloropyridine-2,3-diamine A15 (0.555 g, 3.87 mmol) and 4-(benzyloxy)benzaldehyde A8 (0.861 g, 4.06 mmol) were suspended in water (40 ml_) and the reaction mixture was then heated at reflux for 22 hours. The reaction mixture was cooled and the water was evaporated in vacuo to give a brown solid. The crude material was purified by silica gel chromatography (40 g silica cartridge, 0-75% EtOAc in petroleum benzine 40-60 C) to give the title compound (0.305 g, 23%) as a yellow solid. H NMR (400 MHz, cf DMSO) delta 9.17 (s, 1 H), 8.13 - 8.05 (m, 2H), 7.62 (d, J = 5.1 Hz, 1 H), 7.52 - 7.45 (m, 2H), 7.45 - 7.38 (m, 2H), 7.39 - 7.30 (m, 1 H), 7.20 (d, J = 5.1 Hz, 1 H), 7.16 (d, J = 8.8 Hz, 2H), 5.61 (s, 2H), 5.22 (s, 2H). LCMS-A m/z (positive ion) 338.1 , 340.1 [M+H]+ No UV trace for product.

Reference： [1]Patent: WO2014/128465,2014,A1 .Location in patent: Page/Page column 55

15
[ 19798-80-2 ]
[ 24484-98-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4344 - 4353
[2]Patent: US2016/96834,2016,A1

16
[ 58287-76-6 ]
[ 24484-98-8 ]
4-(7-chloro-3H-imidazo-[4,5-b]pyridin-2-yl)-N,N-dimethylbenzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4344 - 4353

17
[ 24484-98-8 ]
2-(6-cyclopropyl-8-fluoro-1-oxoisoquinolin-2(1H)-yl)-6-(2-(4-(dimethylcarbamoyl)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)benzyl acetate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4344 - 4353

18
[ 24484-98-8 ]
4-(7-(3-(6-cyclopropyl-8-fluoro-1-oxoisoquinolin-2(1H)-yl)-2-(hydroxymethyl)-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylbenzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4344 - 4353

19
[ 619-84-1 ]
[ 24484-98-8 ]
4-(7-chloro-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
582 mg	With sodium hydroxide; at 130℃;	4-(7-chloro-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline 4-Chloro-pyridine-2,3-diamine (2.09 mmol; 1.00 eq.; 300.00 mg), polyphosphoric acid (12750.00 mg) and 4-dimethylaminobenzoic acid (2.51 mmol; 1.20 eq.; 414.20 mg) were heated at 130 C. overnight. The reaction mixture was poured into water/ice (50 ml) and the pH was adjusted with ammonium chloride (18.69 mmol; 8.95 eq.; 1000.00 mg) and NaOH (200.02 mmol; 95.72 eq.; 8000.00 mg) to neutral. Additional Sodium hydroxide was added as single pellets so that the temperature of the aqueous solution not to exceed 50 C (cooling by adding ice pellets from time to time). The product precipitated at pH=8 (litmus paper) and the suspension was chilled at 5 C. in ice for 30 min then filtered on a plastic filter unit. The precipitate was dried under high vacuum to afford the desired compound [4-(7-Chloro-3H-imidazo[4,5-b]pyridin-2-yl)-phenyl]-dimethyl-amine (582.00 mg; 2.13 mmol) as a tan amorphous solid. MS: m/z=273.1 [M+H]+.

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0685

20
[ 30766-15-5 ]
[ 24484-98-8 ]
[6-(7-chloro-3H-imidazo[4,5-b]pyridin-2-yl)-pyridin-3-yl]-dimethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; at 130℃; for 48.0h;	[6-(7-Chloro-3H-imidazo[4,5-b]pyridin-2-yl)-pyridin-3-yl]-dimethyl-amine 4-Chloro-pyridine-2,3-diamine (1.39 mmol; 1.00 eq.; 200.00 mg), polyphosphoric acid (12750.00 mg) and 5-Dimethylamino-pyridine-2-carboxylic acid (1.67 mmol; 1.20 eq.; 277.78 mg) were heated at 130 C. over 2 days. The reaction mixture was then treated with water (50 ml). A spatula was then used to break apart the thick viscous material and dissolve into the water. Some ice was then added and the pH was adjusted with ammonium chloride (18.69 mmol; 13.42 eq.; 1000.00 mg) and NaOH (200.02 mmol; 143.58 eq.; 8000.00 mg) to neutral. The product precipitated at pH=8 (litmus paper) and the suspension was chilled at 5 C. in ice for 30 min then filtered on a plastic filter unit. The precipitate was dried under high vacuum to afford the desired compound [6-(7-Chloro-3H-imidazo[4,5-b]pyridin-2-yl)-pyridin-3-yl]-dimethyl-amine (445.00 mg; 1.63 mmol) as a tan amorphous solid. The material was carried forward without purification. MS: m/z=248.7 [M+H]+.

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0689

21
[ 25016-11-9 ]
[ 24484-98-8 ]
7-chloro-2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.9%	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 80℃; for 10.0h;	7-chloro-2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine To a solution of <strong>[24484-98-8]4-chloropyridine-2,3-diamine</strong> (1.80 g, 12.5 mmol) in DMF (20 mL) was added TPSA (410 mg, 2.38 mmol) and 1-methyl-1H-pyrazole-4-carbaldehyde (1.38 g, 12.5 mmol). The mixture was stirred at 80 C. for 10 hrs. After LC-MS showed the reaction was completed, the reaction mixture was concentrated under reduced pressure to give a residue which was purified by preparative HPLC (neutral condition)s to give 7-chloro-2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine (1.58 g, 53.9% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta: 8.49 (s, 1H), 8.22 (d, J=5.2 Hz, 1H), 8.17 (s, 1H), 7.36 (d, J=5.6 Hz, 1H), 3.95 (s, 3H).

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0265

22
[ 24484-98-8 ]
2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl)benzyl acetate [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

23
[ 24484-98-8 ]
2-(5-fluoro-2-(hydroxymethyl)-3-(2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl)phenyl)-7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

24
[ 24484-98-8 ]
(2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-(2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl)pyridin-3-yl)methyl acetate [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

25
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2-(3-(hydroxymethyl)-4-(2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl)pyridin-2-yl)-7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

26
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8-cyclopropyl-6-fluoro-4-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-5-one [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

27
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2-{4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl}pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

28
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2-(1-methyl-1H-pyrazol-4-yl)-7-(4-pyrrolidin-2-yl-phenyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

29
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(4-tert-butylphenyl)-(2-{4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]-phenyl}-pyrrolidin-1-yl)methanone [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

30
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[ 95-92-1 ]
8-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
284 mg	for 4.0h;Reflux;	General procedure: A mixture of 2,3-diaminopyridine in diethyl oxalate (10 mL/1 mmol phenyldiamine) was heated to reflux for 4 h before cooled to room temperature. The resulted solid was filtered,washed with ethyl acetate and 95% ethanol, decolorized with activated charcoal and recrystallized in water and DMF or DMSO to give 5-azaquinoxalinediones as white solid. 5.2.2.16 8-Chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (16) The title compound was prepared from 2-amino-4-chloropyridine according to the general procedure as white solid (284 mg, 14.4%). IR (KBr) nu 3044, 2743, 1697, 1594, 1373, 1276 cm-1; 1H NMR (400 MHz, DMSO-d6) delta 7.29 (1H, d, J = 5.6 Hz, H-7), 8.01 (1H, d, J = 5.6 Hz, H-6), 11.74 (1H, s, NH-1), 12.50 (1H, s, NH-4); 13C NMR (100 MHz, DMSO-d6) delta 119.18, 119.79, 126.98, 140.28, 142.13, 155.13, 155.57; HRMS-EI C7H4ClN3O2 calcd [M+H]+ 198.0070, found 198.0064.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 117,p. 19 - 32

31
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6-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

32
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[ 122-51-0 ]
[ 6980-11-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 100℃; for 3h;Inert atmosphere;	: A solution of 4-chloropyridme~2,3~diamme (1 g, 6.97 mmol) in CH(OEt)3 (20 mL) and HCOOH (0.5 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 100 C for 3 h under N2. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (20 mL) and extracted with DCM/i-PrOH (20 mL chi 3), The combined organic layers were washed with brine (20 mL), dried over a2SC>4, filtered and concentrated under reduced pressure to give 7-chloro-3H-imidazo[4,5-b]pyridine as a dark brown solid. LCMS: RT 0.140 mm, m/z = 154.1 j M 1 1 ] - H NMR (400 MHz, DMSO-d6): delta 13.43 (br. s, 1H), 8.52 (d, ./ 5.14 Hz, 1 H), 8.29 (d, ./ 5.14 Hz, 1 H), 7.39 (d, ./ 5.15 Hz, 1 H).

Reference： [1]Patent: WO2017/87905,2017,A1 .Location in patent: Page/Page column 201

33
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7-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Reference： [1]Patent: WO2017/87905,2017,A1

34
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7-cyclopropyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Reference： [1]Patent: WO2017/87905,2017,A1

35
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7-cyclopropyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b] pyridine-4-oxide [ No CAS ]

Reference： [1]Patent: WO2017/87905,2017,A1

36
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5-chloro-7-cyclopropyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Reference： [1]Patent: WO2017/87905,2017,A1

37
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7-cyclopropyl-N-(1-methyl-1H-pyrazol-3-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-amine [ No CAS ]

Reference： [1]Patent: WO2017/87905,2017,A1

38
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7-cyclopropyl-N-(1-methyl-1H-pyrazol-3-yl)-3H-imidazo[4,5-b]pyridin-5-amine [ No CAS ]

Reference： [1]Patent: WO2017/87905,2017,A1

39
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(1-(pyrido[2,3-b]pyrazin-8-yl)piperidin-4-yl)methanol [ No CAS ]