[ CAS No. 1260851-42-0 ] {[proInfo.proName]}

Name: 1260851-42-0|Methyl 5-chloro-1H-indazole-7-carboxylate|98%
Brand: Ambeed
SKU: A230204
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Quality Control of [ 1260851-42-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1260851-42-0 ]

SDS Specification

Alternatived Products of [ 1260851-42-0 ]

Product Details of [ 1260851-42-0 ]

CAS No. :	1260851-42-0	MDL No. :	MFCD11975885
Formula :	C₉H₇ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FZWZHQQUHUQHPN-UHFFFAOYSA-N
M.W :	210.62	Pubchem ID :	53419723
Synonyms :

Calculated chemistry of [ 1260851-42-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.38
TPSA :	54.98 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) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	2.03
Log Po/w (WLOGP) :	2.0
Log Po/w (MLOGP) :	1.61
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	1.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.77
Solubility :	0.359 mg/ml ; 0.0017 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.324 mg/ml ; 0.00154 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.61
Solubility :	0.0517 mg/ml ; 0.000245 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 1260851-42-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1260851-42-0 ]

* 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.

Downstream synthetic route of [ 1260851-42-0 ]

[ 1260851-42-0 ] Synthesis Path-Downstream 1~35

1
[ 7252-83-7 ]
[ 1260851-42-0 ]
methyl 5-chloro-2-(dimethoxymethyl)-2H-indazole-7-carboxylate [ No CAS ]
[ 1262420-01-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 11% 2: 22%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide In dimethyl sulfoxide at 80℃;	8.B Step B: Methyl S-chloro-lH-indazole^-carboxylate (2.65 g, 12.6 mmol; 1 eq) from Step A above was stirred in DMSO (25 mL) at room temperature while bromoacetaldehyde dimethyl acetal (3 mL, 25.2 mmol) pre-mixed with potassium iodide (209 mg, 1.3 mmol) was added. l ,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 2 mL, 12.6 mmol) was then added dropwise. The reaction mixture was stirred at 80 0C (external temperature) overnight. The reaction mixture was neutralized with sat. NH4Cl then partitioned between H2O and ethyl acetate. The ethyl acetate layers were combined, dried (Na2SO1J), filtered, concentrated and purified by column chromatography (silica gel, 1 : 1 ethyl acetate/hexanes) to afford methyl 5-chloro-l-(2,2-dimethoxyethyl)-lH-indazole-7- carboxylate as a light yellow oil (404 mg, 1 1%, regioisomer confirmed by NOE): 1H NMR (300 MHz, CDCl3) δ 8.04 (s, IH), 8.84 (s, 2H), 4.93 (d, J = 5.1 Hz, 2H), 4.50 (t, J = 5.1 Hz, I H), 3.99 (s, 3H), 3.27 (s, 6H). [1.29 g starting material recovered; 846 mg, 22% undesired regioisomer methyl 5-chloro-2-(dimethoxymethyl)-2H-indazole-7- carboxylate collected as side product, dark yellow solid]

Reference： [1]Current Patent Assignee: CURIA INC - WO2011/8572, 2011, A2 Location in patent: Page/Page column 65-66

2
[ 79101-83-0 ]
[ 1260851-42-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 2-amino-3-methyl-5-chlorobenzoic acid methyl ester With acetic anhydride In chloroform at 20℃; for 1h; Cooling with ice; Stage #2: With potassium acetate; isopentyl nitrite In chloroform Reflux;	8.A Step A: Methyl 2-amino-5-chloro-3-methylbenzoate (6.6 g, 33.1 mmol) was dissolved in CHCb (90 ttiL) then cooled in an icebath while acetic anhydride (7.2 mL, 76.1 mmol) was added dropwise. After the addition was complete, the reaction mixture was stirred at room temperature for ca 1 h, then KOAc (650 mg, 6.6 mmol) was added, followed by isoamyl nitrite (9.7 mL, 72.8 mmol). The reaction mixture was heated under reflux until the reaction was complete by TLC (overnight). While cooling to room temperature, precipitation was observed. The precipitate was collected and dried to afford methyl 5-chloro-lH-indazole-7-carboxylate as a yellow solid (4.83 g, 69%): 1H NMR (300 MHz, CDCl3) δ 1 1.25 (s, 1 H), 8.10 (s, 1 H), 8.05 (s, 3H), 7.97 (s, 1 H), 4.09 (s, 1 H); MS (ESR) Wz 21 1 (M+H).
1.4 g	Stage #1: 2-amino-3-methyl-5-chlorobenzoic acid methyl ester With tetrafluoroboric acid; sodium nitrite In methanol; water at 0℃; for 1h; Stage #2: With 18-crown-6 ether; potassium acetate In chloroform at 20℃; for 1h;

Reference： [1]Current Patent Assignee: CURIA INC - WO2011/8572, 2011, A2 Location in patent: Page/Page column 65
[2]Giardinetti, Maxime; Marrot, Jérôme; Moreau, Xavier; Coeffard, Vincent; Greck, Christine [Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6855 - 6861]

3
[ 1260851-42-0 ]
[ 1262420-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 80 °C 2.1: hydrogenchloride; water / tetrahydrofuran / Reflux 2.2: pH 8

Reference： [1]Current Patent Assignee: CURIA INC - WO2011/8572, 2011, A2

4
[ 1260851-42-0 ]
[ 1262419-20-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 80 °C 1.2: 2 h / 60 °C 2.1: acetic acid 2.2: Heating

Reference： [1]Manning, David D.; Guo, Cheng; Zhang, Zhenjun; Ryan, Kristen N.; Naginskaya, Jennifer; Choo, Sok Hui; Masih, Liaqat; Earley, William G.; Wierschke, Jonathan D.; Newman, Amy S.; Brady, Catherine A.; Barnes, Nicholas M.; Guzzo, Peter R. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 11, p. 2578 - 2581]

5
[ 7252-83-7 ]
[ 1260851-42-0 ]
[ 1262420-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-bromo-2,2-dimethoxyethane; 5-chloro-1H-indazole-7-carboxylic acid methyl ester With 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide In dimethyl sulfoxide at 80℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 60℃; for 2h;

6
[ 513-38-2 ]
[ 1260851-42-0 ]
5-chloro-1-isobutyl-1H-indazole-7-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	1 General Method 1: Alkylation General procedure: To a solution of 5-substituted-indazole-7-carboxylic acid methyl ester, at room temperature and under nitrogen atmosphere, in N,N-dimethylformamide (0.18M) were added Cesium carbonate (1.2 equiv.) and the corresponding alkylating agent (1.1 equiv.). The resulting mixture was stirred for 18 h. Then, the reaction mixture was concentrated to dryness under vacuum and the residue was partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was separated, washed with Brine, dried (MgSO4), filtered and the solvent evaporated. [0195] The mixture of regioisomers was separated by column chromatography in a SPE Silica cartridge using as eluent a gradient from iso-hexane/ethyl acetate 9:1 to 1:3 to isolate both regioisoisomers as colorless oils.

Reference： [1]Current Patent Assignee: ABBVIE INC - US2015/210689, 2015, A1 Location in patent: Paragraph 0194; 0195; 0197

7
[ 1260851-42-0 ]
1-(5-chloro-1-isobutyl-1H-indazol-7-ylmethyl)-1H-indazole-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere 2: diisobutylaluminium hydride / toluene / 18 h / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 5: sodium hydroxide / 1,4-dioxane; water / 16 h / 60 °C