[ CAS No. 170487-40-8 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 170487-40-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 170487-40-8 ]

SDS Specification

Alternatived Products of [ 170487-40-8 ]

Product Details of [ 170487-40-8 ]

CAS No. :	170487-40-8	MDL No. :	MFCD07371612
Formula :	C₉H₈N₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	TUSICEWIXLMXEY-UHFFFAOYSA-N
M.W :	176.17	Pubchem ID :	286535
Synonyms :

Calculated chemistry of [ 170487-40-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
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 :	47.37
TPSA :	54.98 ?2

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) :	-5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.14
Log Po/w (XLOGP3) :	2.08
Log Po/w (WLOGP) :	1.35
Log Po/w (MLOGP) :	1.04
Log Po/w (SILICOS-IT) :	1.84
Consensus Log Po/w :	1.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.62
Solubility :	0.42 mg/ml ; 0.00238 mol/l
Class :	Soluble
Log S (Ali) :	-2.86
Solubility :	0.241 mg/ml ; 0.00137 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.98
Solubility :	0.183 mg/ml ; 0.00104 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.5

Safety of [ 170487-40-8 ]

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

Application In Synthesis of [ 170487-40-8 ]

* 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 [ 170487-40-8 ]
Downstream synthetic route of [ 170487-40-8 ]

[ 170487-40-8 ] Synthesis Path-Upstream 1~4

1
[ 170487-40-8 ]
[ 74-88-4 ]
[ 1071433-01-6 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium hexamethyldisilazane In tetrahydrofuranHeating / reflux	Methyl 1H-indazole-6-carboxylate was prepared according to the procedure disclosed in J. Med. Chem. 2000, 43 (1 ), 41-58 (example 12b, page 49). Alkylation under standard conditions (sodium hexamethyldisilazide, THF, iodomethane, reflux) provided methyl 2-methyl-2H-indazole-6-carboxylate (44percent). Saponification under standard conditions (1 N NaOH) afforded the title product (53percent).

Reference： [1] Patent: WO2008/65508, 2008, A1, . Location in patent: Page/Page column 28

2
[ 170487-40-8 ]
[ 2533-69-9 ]
[ 1071433-01-6 ]

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 13, p. 1661 - 1663

3
[ 170487-40-8 ]
[ 74-88-4 ]
[ 1007219-73-9 ]
[ 1071433-01-6 ]

Yield	Reaction Conditions	Operation in experiment
130 mg	Stage #1: With sodium hydride In mineral oil at 20℃; for 0.5 h; Cooling with ice	S[00478] To an ice-cooled solution of methyl lH-indazole-6-carboxylate (566 mg, 3.21 mmol) was added NaH (154 mg, 3.85 mmol), the mixture was then stirred at room temperature for 30min. Methyl iodide (547 mg, 3.85 mmol) was added drop wise, and the reaction mixture was stirred overnight. Cooled to 0 °C, added water and extracted with ethyl acetate. The organic phase was concentrated and purified by gel chromatograph to provide 130 mg of methyl 1 -methyl- lH-indazole-6-carboxyl ate and 230 mg of methyl 2 -methyl -2H-indazole-6- carboxylate, 59percent.1H NMR for methyl 1 -methyl- lH-indazole-6-carboxylate: 1H NMR (400 MHz, CDC1₃): δ 3.97 (3H, s), 4.14 (3H, s), 7.74-7.82 (2H, m), 8.02 (1H, s), 8.17 (1H, d, J = 0.8 Hz). 1H NMR for methyl 2-methyl-2H-indazole-6-carboxylate: 1H NMR (400 MHz, CDC13): δ 3.94 (3H, s), 4.25 (3H, s), 7.65-7.72 (2H, m), 7.92 (1H, s), 8.47 (1H, d, J= 1.2 Hz). [M+H] Calc'd for C 10H10N2O2, 191; Found, 191.

Reference： [1] Patent: WO2014/89364, 2014, A1, . Location in patent: Paragraph 00477; 00478

4
[ 170487-40-8 ]
[ 1092961-10-8 ]

Reference： [1] Patent: WO2014/89364, 2014, A1,

[ 170487-40-8 ] Synthesis Path-Downstream 1~4

1
[ 170487-40-8 ]
[ 704-91-6 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 97%	With water; lithium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 16h;	To a stirred solution of compound methyl lH-indazole-6-carboxylate (1.0 g, 5.676 mmol, leq) in tetrahydrofuran/rnethanol/H20 (1:1:1; lOmL) was added LIOH (476 mg, 11.353 mmol, 2 eq) at room temperature then stirred for 16h. The solvents were evaporated, residue diluted with water (lOmL) andacidified with 2N HCI (pH4-5) to get solid precipitate, filtered and dried to get compound 2 (900 mg,?97percent) as off white solid. TLC system: methanol/dichloromethane (1:9), Rf: 0.1.?H NMR (300 MHz, DMSO-d6): oe 13,36 (s, 1H), 13.04 (s, lH), 8.24?8.08 (m, 2H), 7.85 (dd, J 8.5, 0.9 Hz, I H), 7.67 (dd, J = 8.4, 1.3 Hz, I H).
87%	With lithium hydroxide; water; In tetrahydrofuran; at 50℃; for 4h;	b) A solution of compound 26e2 (5.0 g, 28.4 mmol) in THF (56 mL) was treated with LiOH (21 mL of a 2M aqueous solution, 42 mmol), and the reaction mixture is stirred at 50 °C. After 4 hours, the reaction mixture was cooled to room temperature and diluted with water. The basic aqueous layer was rinsed with diethyl ether, acidified to pH 3-4 by the addition of 1 M HCI, and extracted with ethyl acetate. The aqueous layer was extracted further with ethyl acetate, and the combined organic layers were rinsed with brine, dried over MgS04, and concentrated to afford 4.0 g (87percent yield) of compound 26. 3.'H NMR (CD30D) 8 7.79-7. 87 (m, 2H), 8.14 (s, 1H), 8.29 (s, 1H) ; ES (+) MS m/e = 163 (M+1).
85.6%	With water; lithium hydroxide; In tetrahydrofuran; at 50℃; for 4h;	A mixture of intermediate (12) (44.0g, 0.25mol) was dissolved in tetrahydrofuran (a 500 mL) was added 2NLiOH aqueous solution (200mL, 0.40mol), the reaction was stirred at 50 4h. Cooling to room temperature, the tetrahydrofuran was evaporated under reduced pressure, the residue was added distilled water (200 mL), washed with 1NHCl acidified to pH 3.5, added with ethyl acetate (3 × 500mL) extraction, the combined organic layer was washed with brine (a 500 mL), no over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give a pale yellow solid intermediate (13) 34.7g, yield 85.6percent.

85.6%	With water; lithium hydroxide; In tetrahydrofuran; at 50℃; for 4h;	Intermediate (12) (44.0 g, 0.25 mol) was dissolved in tetrahydrofuran (500 mL), and an aqueous solution of 2N LiOH (200 mL, 0.40 mol) was added. The reaction mixture was stirred at 50°C for 4 h, and was then cooled to roomtemperature. Tetrahydrofuran was distilled off under reduced pressure, and the residue was diluted by adding distilledwater (200 mL). The resulting mixture was acidified to pH 3.5 with 1 N HCl, and was extracted with ethyl acetate (33500mL). The combined organic layer was washed with brine (500 mL), dried over anhydrous sodium sulfate, and filtered.The filtrate was concentrated under reduced pressure to obtain intermediate (13) as a light yellow solid (34.7 g, yield:85.6percent).MASS (ESI+) m/z = 163 (M+H)+.1 H NMR (400 MHz, CD3OD): 7.79-7.87 (m, 2H), 8.14 (s, 1H), 8.29 (s, 1H).
85.6%	With water; lithium hydroxide; In tetrahydrofuran; at 50℃; for 4h;	Methyl 1H-indazole-6-carboxylate (44.0 g, 0.25 mol) was dissolved in tetrahydrofuran (500 mL).2N LiOH aqueous solution (200 mL, 0.40 mol) was added.The reaction solution was stirred at 50 ° C for 4 h.After cooling to room temperature, tetrahydrofuran was evaporated under reduced pressure and the residue was diluted with distilled water (200 mL) and acidified to pH 3.5 with 1N HCl.Ethyl acetate (3 × 500 mL) was added for extraction.The mixed organic layer was washed with brine (500 mL).Dry over anhydrous sodium sulfate, filter,The filtrate was concentrated under reduced pressure to give a pale yellowColor solid intermediate (13) 34.7g,The yield was 85.6percent.

Reference： [1]Patent: WO2016/8590,2016,A1 .Location in patent: Page/Page column 56
[2]Patent: WO2005/44817,2005,A1 .Location in patent: Page/Page column 118-119
[3]Patent: CN105693520,2016,A .Location in patent: Paragraph 0196; 0197; 0198; 0199; 0200; 0201
[4]Patent: EP3067351,2016,A1 .Location in patent: Paragraph 0087; 0088
[5]Patent: CN108658947,2018,A .Location in patent: Paragraph 0093; 0157; 0167-0168

2
[ 704-91-6 ]
[ 170487-40-8 ]

Yield	Reaction Conditions	Operation in experiment
6.75 g (82%)	With sulfuric acid; In methanol; water;	1.B 1H-Indazole-6-carboxylic acid methyl ester A mixture of 7.59 g (46.8 mmol, 1.0 equiv) <strong>[704-91-6]1H-<strong>[704-91-6]indazole-6-carboxylic acid</strong></strong> in 500 mL CH3OH and 1 mL conc. H2SO4 was heated to reflux for 8 hours, then allowed to stir at room temperature for 18 hours. The mixture was concentrated to ~200 mL, diluted with 1 L ethyl acetate, and washed 1250 mL saturated aqueous NaHCO3, 1250 mL H2O, 1*250 mL brine, and dried over Na2SO4. The aqueous washes were extracted with two portions of ethyl acetate to recover additional product. The organic layers were combined, concentrated, and dried to give 6.75 g (82percent) of a yellow-orange-tan solid: 1H NMR (300 MHz, CDCl3) delta 10.8 (br s, 1H), 8.28 (dd, 1H, J=0.9, 1.9 Hz), 8.15 (d, 1H, J=1.0 Hz), 7.8 (m, 2H), 3.97 (s, 3H): MS (Cl, NH3) m/z 177 (M+H+, base).

Reference： [1]Patent: US6262040,2001,B1

3
[ 704-91-6 ]
[ 18107-18-1 ]
[ 170487-40-8 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; In diethyl ether; toluene;Product distribution / selectivity;	Step C - Synthesis of Compound 17 D; 17C 17D; A solution of lH-<strong>[704-91-6]indazole-6-carboxylic acid</strong> 17C (1.73 g; 10.70 mmol) in toluene (80 mL) and methanol (30 mL) was treated with a solution of TMS-diazomethane (2 M soln in ether) until evolution of gas stopped. The reaction mixture was concentrated in vacuo and the residue was adsorbed on silica gel. The product was purified on a Biotage 40-M silica gel column (gradient: 0 to 20 percent acetone in hexanes) to give the product 17D (950 mg; 50 percent for <n="113"/>two steps) as a slightly yellow solid. 1H-NMR (CDCl3; 400 MHz): delta 8.28 (IH, s), 8.16 (IH, s), 7.86 (IH, d, J = 8.54 Hz), 7.81 (IH, d, J = 8.54 Hz), 3.98 (3H, s). LR-MS (ESI): caldc for C9H9N2O2 [M+H]+ 177.07; found 177.20.
	With methanol; In diethyl ether; toluene;Product distribution / selectivity;	19C 19D; A solution of lH-<strong>[704-91-6]indazole-6-carboxylic acid</strong> 19C (1.73 g; 10.70 mmol) in toluene (80 mL) and methanol (30 mL) was treated with a solution of TMS-diazomethane (2 M soln in ether) until evolution of gas stopped. The reaction mixture was concentrated in vacuo and the resulting residue was adsorbed on silica gel. The product was purified on a Biotage 40-M silica gel column (gradient: 0 to 20 percent acetone in hexanes) to provide the product 19D (950 mg; 50 percent for two steps) as a slightly yellow solid. 1H-NMR (CDCl3; 400 MHz): delta 8.28 (IH, s), 8.16 (IH, s), 7.86 (IH, d, J = 8.54 Hz), 7.81 (IH, d, J = 8.54 Hz), 3.98 (3H, s). LR-MS (ESI): caldc for C9H9N2O2 [M+H]+ 177.07; found 177.20.

Reference： [1]Patent: WO2009/32125,2009,A1 .Location in patent: Page/Page column 111-112
[2]Patent: WO2009/32124,2009,A1 .Location in patent: Page/Page column 186

4
[ 67-56-1 ]
[ 704-91-6 ]
[ 170487-40-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With diazomethyl-trimethyl-silane; In diethyl ether; toluene;	A solution of IH-indazole-6-carboxyIic acid 14C (1.73 g; 10.70 ramol) in toluene (80 ml) and methanol (30 niL) was treated with a solution of TMS-diazomethaiie (2 M soln in ether) until evolution of gas stopped. The reaction mixture was concentrated in vacuo and the residue was adsorbed on silica gel. The product was purified on a Biotage 40-M silica gel column (gradient: 0 to 20 percent acetone in hexanes) to provide the product 14D (950 rag; 50 percent for two steps) as a slightly yellow solid. 1H-NMR (CDCl3; 400 MHz): delta 8.28 (IH, s), 8.16 (IH, s), 7.86 (IH, d, J = 8.54 Hz), 7.81 (IH, d, J = 8.54 Hz), 3.98 (3H, s). LR-MS (ESI): caldc for C9H9N2O2 [M+H]+ 177.07; found 177.20.
	With sulfuric acid;	Preparation of tert -butyl 5-(hydroxymethyl)-lH-indazole- l -carboxylateThe title compound was synthesized by esterification of <strong>[704-91-6]indazole-6-carboxylic acid</strong> using methanol in presence of cone, sulphuric acid followed by reduction of the ester group using lithium aluminium hydride and its subsequent reaction with di-ter/-butyl dicarbonate anhydride; NMR (300 MHz, DMSO-c 6) delta 1.64 (s, 9H), 4.67 (d, J = 5.1 Hz, l H), 5.43 (br s, I H), 7.29 (d, .] = 7.8 Hz, I H), 7.80 (d, J = 8.1 Hz, 1 H), 8.12 (s, 1 H), 8.36 (s, 1 H).

Reference： [1]Patent: WO2009/152200,2009,A1 .Location in patent: Page/Page column 81; 82
[2]Patent: WO2011/138657,2011,A1 .Location in patent: Page/Page column 54

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H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 170487-40-8 ] {[proInfo.proName]}

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[ 170487-40-8 ] Synthesis Path-Upstream 1~4

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