[ CAS No. 6980-11-6 ] {[proInfo.proName]}

Name: 6980-11-6|7-Chloro-1H-imidazo[4,5-b]pyridine|97%
Brand: Ambeed
SKU: A153583
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Quality Control of [ 6980-11-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6980-11-6 ]

Product Details of [ 6980-11-6 ]

CAS No. :	6980-11-6	MDL No. :	MFCD15143399
Formula :	C₆H₄ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HAWCUEYFSQKISQ-UHFFFAOYSA-N
M.W :	153.57	Pubchem ID :	12782383
Synonyms :

Calculated chemistry of [ 6980-11-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.9
TPSA :	41.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.85
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	1.61
Log Po/w (MLOGP) :	0.78
Log Po/w (SILICOS-IT) :	2.24
Consensus Log Po/w :	1.37

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.33
Solubility :	0.722 mg/ml ; 0.0047 mol/l
Class :	Soluble
Log S (Ali) :	-1.86
Solubility :	2.14 mg/ml ; 0.0139 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.14
Solubility :	0.112 mg/ml ; 0.000728 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 6980-11-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6980-11-6 ]

* 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 [ 6980-11-6 ]
Downstream synthetic route of [ 6980-11-6 ]

[ 6980-11-6 ] Synthesis Path-Upstream 1~6

1
[ 6863-46-3 ]
[ 6980-11-6 ]

Reference： [1] Patent: WO2008/118468, 2008, A1, . Location in patent: Page/Page column 123

2
[ 24484-98-8 ]
[ 122-51-0 ]
[ 6980-11-6 ]

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

3
[ 273-21-2 ]
[ 6980-11-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 12, p. 3165 - 3168
[2] Journal of Heterocyclic Chemistry, 1982, vol. 19, # 3, p. 513 - 517
[3] Patent: WO2009/9740, 2009, A1, . Location in patent: Page/Page column 62
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4362 - 4367

4
[ 6863-46-3 ]
[ 6980-11-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 12, p. 3165 - 3168

5
[ 452-58-4 ]
[ 6980-11-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 12, p. 3165 - 3168

6
[ 6863-46-3 ]
[ 52090-89-8 ]
[ 6980-11-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, # 3, p. 513 - 517

[ 6980-11-6 ] Synthesis Path-Downstream 1~88

1
[ 6863-46-3 ]
[ 52090-89-8 ]
[ 6980-11-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 513 - 517

2
[ 4330-21-6 ]
[ 6980-11-6 ]
7-chloro-3-<2-deoxy-3-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-3H-imidazo<4,5-b>pyridine [ No CAS ]
7-chloro-3-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-3H-imidazo<4,5-b>pyridine [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1996,vol. 79,p. 169 - 178

3
[ 6863-46-3 ]
[ 6980-11-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3165 - 3168

4
[ 18469-52-8 ]
[ 6980-11-6 ]
4-[(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-methyl]-benzoic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3165 - 3168

5
[ 712-76-5 ]
[ 6980-11-6 ]
biphenyl-4-ylmethyl-(3H-imidazo[4,5-b]pyridin-7-yl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3165 - 3168

6
[ 6980-11-6 ]
[ 100-46-9 ]
benzyl-(3H-imidazo[4,5-b]pyridin-7-yl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3165 - 3168

7
[ 452-58-4 ]
[ 6980-11-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3165 - 3168

8
[ 273-21-2 ]
[ 6980-11-6 ]

Yield	Reaction Conditions	Operation in experiment
		[00291] The product was prepared following the procedure from Bioorg. Med. Chem. Lett. 2004, 3165-3168.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3165 - 3168
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 513 - 517
[3]Patent: WO2009/9740,2009,A1 .Location in patent: Page/Page column 62
[4]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4362 - 4367

9
[ 6980-11-6 ]
[ 144952-27-2 ]

Reference： [1]Helvetica Chimica Acta,1996,vol. 79,p. 169 - 178

10
[ 24424-99-5 ]
[ 6980-11-6 ]
[ 878011-41-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With dmap; In dichloromethane; at 20℃; for 0.5h;	To a solution of <strong>[6980-11-6]6-chloro-1-deazapurine</strong> (10 g, 65.1 mmol, J. Heterocyclic Chem. 1982, 19, 513-517) and BOC2O (19.8 g, 91.2 mmol) in dry dichloromethane (100 ml) was added dimethylaminopyridine (0.5 g, 5 mass %) and the mixture was stirred at room temperature for 30 minutes. The reaction was quenched by adding silica and the mixture was filtered over hyflo. Evaporating the solvent yielded the crude product. Trituration with petroleum ether followed by treatment with ether yielded the product as a white solid (6.29 g, 76%), mp: 183.5 C. decomposition 1H NMR (d6-DMSO) delta 8.89 (s, 1H, H-8), 8.47-8.46 (d, J 5.3 , 1H, H-2), 7.62-7.61 (1H, d, J 5.3, H-1), 1.66 ( s, 9H t-Bu).
	With dmap; In acetonitrile; at 20℃;	Example 65; Mcpba (8.7 g, 50 mmol) was added at room temperature to 3H-imidazo[4,5- b]pyridine (5.0 g, 42 mmol) in acetic acid (84 mL, 1469 mmol). The mixture was stirred for 3 hours. The resulting precipitate was filtered and rinsed with Et2O, it gave 4-azabenzimidazole-N-oxide. To 4-azabenzimidazole-N-oxide (2.0Og, 14.8 mmol) phosphorous oxychloride (25.00 mL, 266 mmol) was added at room temperature. The solution was heated to 90C for 18 h. The solution was cooled and the rest POC13 was distilled off in vacuo. The residue was dissolved in CH3CN and quenched with slow addition of ice-water. The mixture was basified to PH 9 with 50% NaOH solution. At room temperature the resulting precipitates were filtered. The collected solid was dissolved in MeOH and insoluble residue was removed by filtration. The filtrates were concentrated and the residue was purified by flash chromatography over silica gel, using 3:7 EtOAc-hexane, gave <strong>[6980-11-6]7-chloro-3H-imidazo[4,5-b]pyridine</strong> (1.2Og, 52.8%). To the mixture of di-tert- butylpyrocarbonate (1193 mg, 5465 mumol), <strong>[6980-11-6]7-chloro-3H-imidazo[4,5-b]pyridine</strong> (0.763 g, 4968 mumol) in acetonitrile (15 mL ), 4-(dimethylamino)pyridine (61 mg, 497 mumol) was added. The mixture was stirred at room temperature overnight. Evaporation of the solvent, flash chromatography of the residue over silica gel , using 0% to 25% EtOAc/hexane, gave tert-butyl 7-chloro-3H-imidazo[4,5- b]pyridine-3-carboxylate, Mass Spectrum (ESI) m/e = 253.0 (M + 1).

Reference： [1]Patent: US2006/52412,2006,A1 .Location in patent: Page/Page column 4
[2]Patent: WO2008/118468,2008,A1 .Location in patent: Page/Page column 123

11
[ 6980-11-6 ]
[ 115953-91-8 ]

Yield	Reaction Conditions	Operation in experiment
7.2 g (35%)	With sodium hydroxide; aniline; In water; benzene;	Method A To <strong>[6980-11-6]7-chloro-3H-imidazo(4,5-b)pyridine</strong> (16 g, 97 mmol) was added aniline (200 mL, 2.1 mol). The resulting mixture was heated under a nitrogen atmosphere at 130 C. for 24 hours. Benzene was added to the cooled mixture and the precipitate was filtered. The solid was dissolved in water and 1N NaOH was added to give a pH reading of 9. The precipitate was filtered and recrystallized from EtOH (decolorized by charcoal) to give 7.2 g (35%) of the 7-anilino-3H-imidazo[4,5-b]pyridine, m.p. 251-252 C. Anal. Calcd. for C12 H10 N4: C, 68.56; H, 4.79; N, 26.65. Found: C, 68.50 H, 4.81; N, 26.62.

Reference： [1]Patent: US4780452,1988,A

12
[ 6980-11-6 ]
7-chloro-3H-imidazo[4,5-b]pyridine-4-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid; In ethanol; acetic acid;	EXAMPLE 13 7-Chloro-3H-imidazo[4,5-b]pyridine-4-oxide 7-Chloro-3H-imidazo[4,5-b]pyridine (15 g, 97.7 mMol) was dissolved in 150 mL of glacial acetic acid and m-chloroperbenzoic acid (23 g, 131 mMol) was added in portions to the stirred solution. After 12 hours the solid was isolated and washed with ether. The solid was suspended in 400 mL of hot ethanol, stirred, and isolated. The product, <strong>[6980-11-6]7-chloro-3H-imidazo[4,5-b]pyridine</strong>-4-oxide, was dried in vacuo. Yield 14.98 g (8.83 mMol, 90.4%); m.p. 200 C. (dec). Anal. calcd. for C6 H4 ClN3 O: C, 42.50; H, 2.38; N, 24.78; Cl, 20.91. Found: C, 42.23; H, 2.39; N, 24.70; Cl, 20.73.

Reference： [1]Patent: US4780452,1988,A

13
[ 6863-46-3 ]
[ 6980-11-6 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; at 20 - 90℃; for 18h;	Example 65; Mcpba (8.7 g, 50 mmol) was added at room temperature to 3H-imidazo[4,5- b]pyridine (5.0 g, 42 mmol) in acetic acid (84 mL, 1469 mmol). The mixture was stirred for 3 hours. The resulting precipitate was filtered and rinsed with Et2O, it gave 4-azabenzimidazole-N-oxide. To 4-azabenzimidazole-N-oxide (2.0Og, 14.8 mmol) phosphorous oxychloride (25.00 mL, 266 mmol) was added at room temperature. The solution was heated to 90C for 18 h. The solution was cooled and the rest POC13 was distilled off in vacuo. The residue was dissolved in CH3CN and quenched with slow addition of ice-water. The mixture was basified to PH 9 with 50% NaOH solution. At room temperature the resulting precipitates were filtered. The collected solid was dissolved in MeOH and insoluble residue was removed by filtration. The filtrates were concentrated and the residue was purified by flash chromatography over silica gel, using 3:7 EtOAc-hexane, gave 7-chloro-3H-imidazo[4,5-b]pyridine (1.2Og, 52.8%). To the mixture of di-tert- butylpyrocarbonate (1193 mg, 5465 mumol), 7-chloro-3H-imidazo[4,5-b]pyridine (0.763 g, 4968 mumol) in acetonitrile (15 mL ), 4-(dimethylamino)pyridine (61 mg, 497 mumol) was added. The mixture was stirred at room temperature overnight. Evaporation of the solvent, flash chromatography of the residue over silica gel , using 0% to 25% EtOAc/hexane, gave tert-butyl 7-chloro-3H-imidazo[4,5- b]pyridine-3-carboxylate, Mass Spectrum (ESI) m/e = 253.0 (M + 1).

Reference： [1]Patent: WO2008/118468,2008,A1 .Location in patent: Page/Page column 123

14
[ 6980-11-6 ]
[ 1100318-98-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With phosphoric acid; hydrogen iodide; In water; at 55 - 70℃; for 20h;	Example 507-(4-Methylpyridin-3-y -3-(2,2,2-trifluoroethyl)-3H-imidazo[4,5-b]pyridine Preparation 50A: 7-Iodo-3H-imid -b]pyridine[00156] A suspension of <strong>[6980-11-6]7-chloro-3H-imidazo[4,5-b]pyridine</strong> (1.6 g, 10.42 mmol) and phosphorous acid (0.427 g, 5.21 mmol) in hydroiodic acid (33.3 mL, 208.4 mmol) was heated at 55 C for 18h and then at 70 C for 2h. The reaction mixture was then cooled to room temperature and filtered. The yellow solid collected was washed with copious amounts of ice-cold water and then dried under high vacuum to afford Preparation 50A (1.96 g, 8 mmol, 77% yield) as a pale yellow solid. ESI MS (M+H)+ = 246.06. HPLC peak tr = 1.912 minutes. HPLC conditions: PHENOMENEX column, 2.0x50 mm. 4 min. gradient (0-100% B), 0.8 mL/min., 40 C (at) 254 nm; Solvent A: 0.1% TFA in 10% MeOH-90% H20; Solvent B: 0.1% TFA in 90% MeOH-10% H20.
	With hydrogen iodide; In water;	[00297] A mixture of <strong>[6980-11-6]7-chloro-3H-imidazo[4,5-b]pyridine</strong> (1.47 g, 9.64 mmol) and 15 mL of 57% hydriodic acid were reacted at 8O0C for 4 hours.After the solid was filtered off it was resubmitted to the reaction with 10 mL of fresh 57% hydriodic acid. The reaction yielded 1.3 g of the product as a black powder, 90% pure.

Reference： [1]Patent: WO2012/44537,2012,A1 .Location in patent: Page/Page column 64-65
[2]Patent: WO2009/9740,2009,A1 .Location in patent: Page/Page column 62-63

15
[ 1262441-70-2 ]
[ 6980-11-6 ]
[ 1262440-70-9 ]

Yield	Reaction Conditions	Operation in experiment
10%		A solution of 7-[(1S)-1-aminoethyl]-6-(3-fluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (50 mg, 0.16 mmol), <strong>[6980-11-6]7-chloro-3H-imidazo[4,5-b]pyridine</strong> (51 mg, 0.33 mmol), and N,N-diisopropylethylamine (57 muL, 0.33 mmol) in 1-butanol (0.5 mL) in a sealable vial was degassed with nitrogen, sealed, and heated at 140 C. for 48 hours. The reaction mixture was diluted with methanol and purified by RP-HPLC (XBridge C18 column, eluding with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (7 mg, 10%) as a white solid. LCMS for C21H18FN6OS (M+H)+: m/z=420.8. 1H NMR (400 MHz, CD3OD): delta 8.04 (s, 1H), 7.83 (d, J=5.9 Hz, 1H), 7.55-7.49 (m, 1H), 7.23-7.12 (m, 3H), 6.86 (d, J=1.2 Hz, 1H), 5.96 (d, J=5.9 Hz, 1H), 4.69-4.67 (m, 1H), 2.75 (s, 3H), 1.57 (d, J=6.4 Hz, 3H).

Reference： [1]Patent: US2011/15212,2011,A1 .Location in patent: Page/Page column 56

16
[ 824-94-2 ]
[ 6980-11-6 ]
7-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	To a 2-dram vial were added 7-chloro-1H-pyrazolo[4,3-b]pyridine (0.200 g, 1.302 mmol), potassium carbonate (0.540 g, 3.91 mmol), and DMF (2.5 mL). With stirring, 1- (chloromethyl)-4-methoxybenzene (0.245 g, 1.563 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. Water was added with ethyl acetate and the contents were transferred to a separatory funnel. The layers were separated and the organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography and following evaporation of the fractions, afforded 7-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5- b]pyridine. MS (M+1) m/z: 274.0 (MH+). LC retention time 1.21 min [A1].

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1611 - 1614
[2]Patent: WO2019/99336,2019,A1 .Location in patent: Page/Page column 140

17
[ 6980-11-6 ]
[ 1361413-74-2 ]