[ CAS No. 1101120-47-1 ] {[proInfo.proName]}

Name: 1101120-47-1|5-Chloropyrazolo[1,5-a]pyridine|98%
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SKU: A158925
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Quality Control of [ 1101120-47-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1101120-47-1 ]

SDS Specification

Alternatived Products of [ 1101120-47-1 ]

Product Details of [ 1101120-47-1 ]

CAS No. :	1101120-47-1	MDL No. :	MFCD21603615
Formula :	C₇H₅ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VYVNNYNNKWOZOJ-UHFFFAOYSA-N
M.W :	152.58	Pubchem ID :	58763965
Synonyms :

Calculated chemistry of [ 1101120-47-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.2
TPSA :	17.3 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) :	-6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	1.69
Log Po/w (WLOGP) :	1.99
Log Po/w (MLOGP) :	1.99
Log Po/w (SILICOS-IT) :	1.63
Consensus Log Po/w :	1.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.52
Solubility :	0.464 mg/ml ; 0.00304 mol/l
Class :	Soluble
Log S (Ali) :	-1.67
Solubility :	3.28 mg/ml ; 0.0215 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.68
Solubility :	0.316 mg/ml ; 0.00207 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 1101120-47-1 ]

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

Application In Synthesis of [ 1101120-47-1 ]

* 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 [ 1101120-47-1 ]
Downstream synthetic route of [ 1101120-47-1 ]

[ 1101120-47-1 ] Synthesis Path-Upstream 1~3

1
[ 1101120-37-9 ]
[ 1101120-47-1 ]

Yield	Reaction Conditions	Operation in experiment
13%	Stage #1: With hydrogenchloride; copper(l) chloride; sodium nitrite In water at 0 - 80℃; for 0.783333 h; Stage #2: With sodium hydroxide In water	Decarboxylation of ester 3l (1.29 g, 2.98 mmol), except with carrying out the aqueous extraction from pH 12, gave pyrazolo[1,5-a]pyridin-5-amine (7l) as a pale brown solid (310 mg, 78percent). ¹H NMR δ (400 MHz, CDCl₃) 8.23 (d, J = 7.4 Hz, 1H), 7.79 (d, J = 2.0 Hz, 1H), 6.58 (d, J = 2.4 Hz, 1H), 6.22 (dd, J = 7.4, 2.4 Hz, 1H), 6.13 (d, J = 2.0 Hz, 1H), 3.81 (s, 2H). LC-MS (APCI⁺) 134 (MH⁺, 100percent). A solution of NaNO₂ (27 mg, 0.39 mmol) in water (1 mL) was added dropwise to a solution of 7l (40 mg, 0.30 mmol) and CuCl (74 mg, 0.75 mmol) in concentrated HCl (1 mL) at 0 °C over 2 min. After 30 min, the reaction mixture was heated to 80 °C for 15 min, and then cooled to room temperature, basified to pH 10 with 1 M NaOH, filtered through a plug of celite and washed with CH₂Cl₂. The layers of the filtrate were separated and the aqueous layer extracted with CH₂Cl₂. The combined extracts were dried (Na₂SO₄) and the solvent removed in vacuo. Chromatography (eluting with hexanes: EtOAc 3:1) gave 5-chloropyrazolo[1,5-a]pyridine (7o) as a white solid (6 mg, 13percent). ¹H NMR δ (400 MHz, CDCl₃) 8.38 (d, J = 7.4 Hz, 1H), 7.95 (d, J = 2.2 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.71 (dd, J = 7.4, 2.2 Hz, 1H), 6.47 (d, J = 1.8 Hz, 1H). LC-MS (APCI⁺) 153 (MH⁺ with ³⁵Cl, 100percent), 155 (MH⁺ with ³⁷Cl, 30percent). Vilsmeier reaction of 7o (6 mg, 0.039 mmol) gave 4o as a white solid (7 mg, 100percent).
13%	Stage #1: With hydrogenchloride; copper(l) chloride; sodium nitrite In water at 0 - 80℃; for 0.783333 h; Stage #2: at 20℃;	Step 13.1 : A solution of NaNO₂ (27 mg, 0.39 mmol) in water (1 mL) was added dropwise to a solution of pyrazolo[1 ,5-a]pyridin-5-amine (34) (40 mg, 0.30 mmol) and CuCI (74 mg, 0.75 mmol) in concentrated HCI (1 mL) at 0 ⁰C over 2 min. After 30 min, the reaction mixture was heated to 80 ⁰C for 15 min, and then cooled to room temperature, basified to pH 10 with 1M NaOH, filtered through a plug of celite and washed with CH₂CI₂. The layers of the filtrate were separated and the aqueous layer extracted with CH₂CI₂. The combined extracts were dried (Na₂SO₄) and the solvent removed in vacuo. Chromatography (eluting with hexanes: EtOAc 3:1) gave 5-chloropyrazolo[1 ,5-a]pyridine (39: X = Cl) as a white solid (6 mg, 13percent). ¹H NMR δ (400 MHz, CDCI₃) 8.38 (d, J 7.4 Hz, 1 H), 7.95 (d, J 2.2 Hz, 1 H), 7.53 (d, J 1.8 Hz, 1 H), 6.71 (dd, J 7.4, 2.2 Hz, 1 H), 6.47 (d, J1.8 Hz, 1 H). LCMS (APCI⁺) 153 (MH⁺ with ³⁵CI, 100percent), 155 (MH⁺ with ³⁷CI, 30percent).

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 69 - 85
[2] Patent: WO2009/8748, 2009, A1, . Location in patent: Page/Page column 68

2
[ 1101120-33-5 ]
[ 1101120-47-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 69 - 85

3
[ 98400-69-2 ]
[ 1101120-47-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 69 - 85

[ 1101120-47-1 ] Synthesis Path-Downstream 1~8

2
[ 1101120-37-9 ]
[ 1101120-47-1 ]

Yield	Reaction Conditions	Operation in experiment
13%		Decarboxylation of ester 3l (1.29 g, 2.98 mmol), except with carrying out the aqueous extraction from pH 12, gave <strong>[1101120-37-9]pyrazolo[1,5-a]pyridin-5-amine</strong> (7l) as a pale brown solid (310 mg, 78%). 1H NMR delta (400 MHz, CDCl3) 8.23 (d, J = 7.4 Hz, 1H), 7.79 (d, J = 2.0 Hz, 1H), 6.58 (d, J = 2.4 Hz, 1H), 6.22 (dd, J = 7.4, 2.4 Hz, 1H), 6.13 (d, J = 2.0 Hz, 1H), 3.81 (s, 2H). LC-MS (APCI+) 134 (MH+, 100%). A solution of NaNO2 (27 mg, 0.39 mmol) in water (1 mL) was added dropwise to a solution of 7l (40 mg, 0.30 mmol) and CuCl (74 mg, 0.75 mmol) in concentrated HCl (1 mL) at 0 C over 2 min. After 30 min, the reaction mixture was heated to 80 C for 15 min, and then cooled to room temperature, basified to pH 10 with 1 M NaOH, filtered through a plug of celite and washed with CH2Cl2. The layers of the filtrate were separated and the aqueous layer extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with hexanes: EtOAc 3:1) gave 5-chloropyrazolo[1,5-a]pyridine (7o) as a white solid (6 mg, 13%). 1H NMR delta (400 MHz, CDCl3) 8.38 (d, J = 7.4 Hz, 1H), 7.95 (d, J = 2.2 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.71 (dd, J = 7.4, 2.2 Hz, 1H), 6.47 (d, J = 1.8 Hz, 1H). LC-MS (APCI+) 153 (MH+ with 35Cl, 100%), 155 (MH+ with 37Cl, 30%). Vilsmeier reaction of 7o (6 mg, 0.039 mmol) gave 4o as a white solid (7 mg, 100%).
13%		Step 13.1 : A solution of NaNO2 (27 mg, 0.39 mmol) in water (1 mL) was added dropwise to a solution of pyrazolo[1 ,5-a]pyridin-5-amine (34) (40 mg, 0.30 mmol) and CuCI (74 mg, 0.75 mmol) in concentrated HCI (1 mL) at 0 0C over 2 min. After 30 min, the reaction mixture was heated to 80 0C for 15 min, and then cooled to room temperature, basified to pH 10 with 1M NaOH, filtered through a plug of celite and washed with CH2CI2. The layers of the filtrate were separated and the aqueous layer extracted with CH2CI2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with hexanes: EtOAc 3:1) gave 5-chloropyrazolo[1 ,5-a]pyridine (39: X = Cl) as a white solid (6 mg, 13%). 1H NMR delta (400 MHz, CDCI3) 8.38 (d, J 7.4 Hz, 1 H), 7.95 (d, J 2.2 Hz, 1 H), 7.53 (d, J 1.8 Hz, 1 H), 6.71 (dd, J 7.4, 2.2 Hz, 1 H), 6.47 (d, J1.8 Hz, 1 H). LCMS (APCI+) 153 (MH+ with 35CI, 100%), 155 (MH+ with 37CI, 30%).

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 69 - 85
[2]Patent: WO2009/8748,2009,A1 .Location in patent: Page/Page column 68

3
[ 1101120-33-5 ]
[ 1101120-47-1 ]