[ CAS No. 73895-37-1 ]

Name: 73895-37-1|5-Chloro-3H-[1,2,3]triazolo[4,5-b]pyridine|95%
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3d Animation Molecule Structure of 73895-37-1

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Quality Control of [ 73895-37-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 73895-37-1 ]

SDS Specification

Alternatived Products of [ 73895-37-1 ]

Product Details of [ 73895-37-1 ]

CAS No. :	73895-37-1	MDL No. :	MFCD18258955
Formula :	C₅H₃ClN₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VWIPQRGRUVTCMF-UHFFFAOYSA-N
M.W :	154.56 g/mol	Pubchem ID :	20154363
Synonyms :

Calculated chemistry of [ 73895-37-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.69
TPSA :	54.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.11
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	1.01
Log Po/w (MLOGP) :	0.79
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	1.21

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.3
Solubility :	0.782 mg/ml ; 0.00506 mol/l
Class :	Soluble
Log S (Ali) :	-2.06
Solubility :	1.33 mg/ml ; 0.00862 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.77
Solubility :	0.264 mg/ml ; 0.00171 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 73895-37-1 ]

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 [ 73895-37-1 ]

* 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 [ 73895-37-1 ]
Downstream synthetic route of [ 73895-37-1 ]

[ 73895-37-1 ] Synthesis Path-Upstream 1~3

1
[ 40851-95-4 ]
[ 73895-37-1 ]

Reference： [1] Chemische Berichte, 1927, vol. 60, p. 775[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417
[3] Patent: WO2009/155156, 2009, A1, . Location in patent: Page/Page column 70

2
[ 27048-04-0 ]
[ 73895-37-1 ]

Reference： [1] Patent: WO2009/155156, 2009, A1,

3
[ 4214-75-9 ]
[ 73895-37-1 ]

Reference： [1] Chemische Berichte, 1927, vol. 60, p. 775[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417
[3] Chemische Berichte, 1927, vol. 60, p. 775[4] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417

[ 73895-37-1 ] Synthesis Path-Downstream 1~8

1
[ 40851-95-4 ]
[ 73895-37-1 ]

Yield	Reaction Conditions	Operation in experiment
		Step l 5-Chloro-lH-fL231triazolor4.5-Mrhovridine6-Chloropyridine-2 ,3 -diamine (Example 23, Step 1) (226 mg, 1.57 mmol) was taken up in warm water (6.3 ml). Sulfuric acid (0.26 ml, 4.72 mmol) was added, and the solution was cooled to -15C. In a separate flask, sodium nitrite (119 mg? 1.73 mmol) was dissolved in 2 mL cold water. The sodium nitrite solution was added dropwise to the reaction mixture over 15 minutes. The mixture was allowed to stir at -15C for 1 hour, then filtered, and the yellow- brown precipitate was collected. The solid was recrystallized from water to yield the title compound as a yellow-brown solid. The filtrate from the separation was neutralized with aqueous sodium bicarbonate and extracted 3x with ethyl acetate. All organic fractions were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an additional portion of the title compound as a yellow-brown solid.LRMS (APCI) calc'd for (CsH4ClN4) [M+H]+, 156; found 155.

Reference： [1]Chemische Berichte,1927,vol. 60,p. 775
Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1927,vol. 59,p. 417
[2]Patent: WO2009/155156,2009,A1 .Location in patent: Page/Page column 70

3
[ 4214-75-9 ]
[ 73895-37-1 ]

Reference： [1]Chemische Berichte,1927,vol. 60,p. 775
Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1927,vol. 59,p. 417
[2]Chemische Berichte,1927,vol. 60,p. 775
Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1927,vol. 59,p. 417

4
[ 73895-37-1 ]
[ 18739-38-3 ]
[ 934706-69-1 ]
[ 934706-68-0 ]

Yield	Reaction Conditions	Operation in experiment
23%; 14%	With triethylamine; In tetrahydrofuran; at 20℃;	(5-chloro-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-(4-methylpiperidin-1-yl)-methanone 5-Chloro-3H-[1,2,3]triazolo[4,5-b]pyridine (100 mg, 0.65 mmol) were dissolved in 10 ml of THF. Then triethylamine (135 μl, 0.97 mmol) and 4-methylpiperidin-1-carbonyl chloride (146 mg, 0.9 mmol) were added and stirred at room temperature for 4 h and left to stand overnight. The reaction mixture was concentrated and the residue was mixed with water and ethyl acetate. The organic phase was separated off, the aqueous phase was extracted once more, and the combined organic phases were washed with water and concentrated. The crude product was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield:

Reference： [1]Patent: US2009/30011,2009,A1 .Location in patent: Page/Page column 20-21

5
[ 73895-37-1 ]
[ 199480-42-7 ]
[ 934706-67-9 ]
[ 934706-66-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; triethylamine; at 20℃; for 9h;	(5-chloro-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-(3,4-dihydro-1H-isoquinolin-2-yl)-methanone 5-Chloro-3H-[1,2,3]triazolo[4,5-b]pyridine (500 mg, 3.23 mmol) and 3,4-dihydro-1H-isoquinoline-2-carbonyl chloride (950 mg, 4.85 mmol) were dissolved in 25 ml of pyridine. Then triethylamine (675 μl, 4.85 mmol) was added and stirred at room temperature for 9 h and left to stand overnight. The reaction mixture was concentrated and the residue was mixed with water and ethyl acetate. The organic phase was separated off, the aqueous phase was extracted once more, and the combined organic phases were washed with water and concentrated. The crude product was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA).

Reference： [1]Patent: US2009/30011,2009,A1 .Location in patent: Page/Page column 20

6
[ 558-30-5 ]
[ 73895-37-1 ]
[ 1201924-49-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In N,N-dimethyl-formamide; at 60 - 85℃;	Step 1 1 -(5-Chloro-lg-rU2,31triazolo\|[4.5-lpyridin- 1 -ylV2-methylpropan-2-ol5-CWoro-lH-[l,2,3]triazolo[4,5-]pyridine (Example 27, Step 1)(285 mg, 1.85 mmol) and 2,2-dimethyloxirane (0.18 mL, 1.94 mmol) were taken-up in DMF (7.4 mL) and potassium tert-butoxide (310 mgf 2.77 mmol) was added. The mixture was heated to 6O0C overnight and then to 85 C for an additional 36 hours. The mixture was then cooled to room temperature, diluted with saturated aqueous ammonium chloride, and extracted with ethyl acetate (3x). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo and purified via reverse phase HPLC (10-100% acetonitrile/water + 0.05% TFA modifier). Desired fractions were lyophilized to afford the title compound as a yellow solid. LRMS (APCI) calc'd for (C9HuClN4O) [M+H]+, 227; found 227.

Reference： [1]Patent: WO2009/155156,2009,A1 .Location in patent: Page/Page column 72

7
[ 27048-04-0 ]
[ 73895-37-1 ]

Reference： [1]Patent: WO2009/155156,2009,A1

8
[ 73895-37-1 ]
[ 74-88-4 ]
5-chloro-3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridine [ No CAS ]
5-chloro-2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridine [ No CAS ]
5-chloro-1-methyl-1H-[1,2,3]triazolo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		NaH (388 mg, 9.70 mmol, 60% purity) was added to a solution of 5-chloro-3H-[l,2,3]triazolo[4,5-b]pyridine (750 mg, 4.85 mmol) in MeCN (20 mL) at 0C and the mixture stirred at 20C for 0.5 h. CH3I (1.03 g, 7.27 mmol) was added and the mixture stirred at 20C for 2 hours. The reaction was quenched with saturated aq. NH4CI (20 mL) and extracted with EtOAc (3 x 30 mL). The combined extracts were dried (NaiSCL) and evaporated to dryness in vacuo and the residue purified by column chromatography on silica gel (petroleum ether/EtOAc; 1:0 to 1: 1) to afford 5-chloro-l-methyl-lH-[l,2,3]triazolo[4,5- b]pyridine (Intermediate 52) (210 mg, 25%) and a mixture of 5-chloro-3-methyl-3H-[l,2,3]triazolo[4,5-b]pyridine (Intermediate 50) and 5-chloro-2-methyl-2H-[l,2,3]triazolo[4,5-b]pyridine (Intermediate 51) (300 mg, 37%) as a yellow solid.Intermediate 48 and 49 (Mixture). 1H NMR (500 MHz, CDCl3) d: 8.31 (d, 7=8.5 Hz, 1H), 8.16 (d, 7=9.0 Hz, 1H), 7.34-7.37 (m, 2H), 4.52 (s, 3H), 4.37 (s, 3H). 5-chloro-3-methyl-3H-[l,2,3]triazolo[4,5-b]pyridine: Intermediate 50. 1H NMR (500 MHz, CDCl3) d: 7.90 (d, 7=8.5 Hz, 1H), 7.47 (d, 7=8.5 Hz, 1H), 4.35 (s, 3H).

Reference： [1]Patent: WO2020/163193,2020,A1 .Location in patent: Paragraph 00297

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H200	Unstable explosive
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 73895-37-1 ]

Quality Control of [ 73895-37-1 ]

Related Doc. of [ 73895-37-1 ]

Product Details of [ 73895-37-1 ]

Calculated chemistry of [ 73895-37-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 73895-37-1 ]

Application In Synthesis of [ 73895-37-1 ]

[ 73895-37-1 ] Synthesis Path-Upstream 1~3

[ 73895-37-1 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 73895-37-1 ]

Chlorides

Related Parent Nucleus of [ 73895-37-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 73895-37-1 ]

Related Parent Nucleus of
[ 73895-37-1 ]