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Chemical Structure| 261953-36-0
Chemical Structure| 261953-36-0
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Product Details of [ 261953-36-0 ]

CAS No. :261953-36-0 MDL No. :MFCD04114695
Formula : C7H5IN2 Boiling Point : -
Linear Structure Formula :- InChI Key :RSGAXJZKQDNFEP-UHFFFAOYSA-N
M.W : 244.03 Pubchem ID :12991241
Synonyms :

Calculated chemistry of [ 261953-36-0 ]

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 : 1.0
Molar Refractivity : 48.81
TPSA : 28.68 Ų

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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 2.04
Log Po/w (SILICOS-IT) : 3.04
Consensus Log Po/w : 2.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.41
Solubility : 0.096 mg/ml ; 0.000394 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.893 mg/ml ; 0.00366 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.87
Solubility : 0.0331 mg/ml ; 0.000136 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 261953-36-0 ]

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 [ 261953-36-0 ]

* 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.

  • Upstream synthesis route of [ 261953-36-0 ]
  • Downstream synthetic route of [ 261953-36-0 ]

[ 261953-36-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 6967-12-0 ]
  • [ 261953-36-0 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h;
Stage #2: With potassium iodide In dichloromethane; water at 0 - 40℃; for 2.16667 h;
A concentrated hydrochloric acid (35 mL, 420 mmol) and an aqueous solution (30 mL) of sodium nitrite (6.64g, 96 mmol) were added to a suspension prepared by adding water (30 mL) to 6-aminoindazole (10.4 g, 78 mmol) at0°C and stirred at 0°C for 30 minutes. Subsequently, to this solution, an aqueous solution (30 mL) of potassium iodide(15.91 g, 96 mmol) was added at 0°C, stirred at room temperature for 30 minutes, to which dichloromethane (80 mL)was then added, and stirred at 40°C for 2 hours. The reaction mixture was cooled down to 0°C, then adjusted to pH =14 with a 3N sodium hydroxide aqueous solution, and the precipitate was taken by filtration. The resulting precipitatewas washed with 10percent sodium thiosulfate, dissolved in tetrahydrofuran, and then silica gel was added. After stirring atroom temperature for 1 hour, hexane (600 mL) was added and filtered. The residue was washed twice with a THF/hexane(1/3 (v/v)) solution, then the solvent was distilled away under a reduced pressure to obtain the title compound (15.23 g,80percent) as an orange powder.1H NMR (400 MHz, CDCl3) δ 10.24 (1H, br, s), 8.04 (1H, br s), 7.92 (1H, br s), 7.51 (1H, br d, J = 8.4 Hz), 7.46 (1H, dd,J = 8.4, 1.2 Hz).
48% With sodium hydroxide; concentrated aqueous HCl; Ki; sodium hydrogencarbonate; sodium nitrite In tetrahydrofuran; hexane; water (i)
To 6-aminoindazole (40.8 g, 0.3065 mol, 1 equiv) in a 2-liter (2-L) round-bottom flask containing a large magnetic stir bar was added ice (256 g), followed by water (128 mL) and the reaction vessel was lowered into an ice bath.
To this stirring slurry at 0° C. was added concentrated aqueous HCl (128 mL, 1.53 mol, 5 equiv).
Immediately after, a solution of NaNO2 (23.3 g, 0.338 mol, 1.1 equiv) in water (96 mL) was added.
After 10 min of stirring at 0° C., KI (61 g, 0.368 mol, 1.2 equiv) was added very slowly at first (~100 mg at a time because the first small bits of KI cause an abrupt evolution of gas) then more rapidly (5 min total time).
The cold bath was removed and the reaction mixture was warmed to 40° C. (gas evolved).
When the rate of gas evolution decreased (~30 min) the reaction mixture was warmed to 50° C. for 30 min.
The mix was then cooled to 23° C., and 3N NaOH (320 mL) was added to neutralize followed by 50percent saturated NaHCO3 (320 mL).
The slurry was then filtered through a Buchner funnel to give a dark reddish-brown solid.
The solid was taken up in warm THF (800 mL) and silica (600 mL dry) was added with stirring.
To this slurry was added hexane (1.2 L) and the mix was vacuum filtered through a pad of silica (300 mL) in a large fritted filter.
The silica was further washed with 2 L of 40percent THF in hexane.
The filtrates were combined and concentrated under reduced pressure to give a solid.
The solid was further triturated with ethyl acetate (~100 mL), filtered and dried under reduced pressure to give 6-iodo-1H-indazole as a light brown solid (36.1 g, 48percent yield): Rf sm 0.12, p 0.48 (Hex-EtOAc 1:1); 1H NMR (300 MHz, CDCl3) 7.9 (s, 1H), 7.8 (s, 1H), 7.42 (d, 1H), 7.33 (d, 1H); MS (ES) [m+H]/z Calc'd 245, Found 245, [m-H]/z Calc'd 243, Found 243.
0.9 g
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667 h;
Stage #2: With potassium iodide In water at 40 - 50℃; for 1.16667 h;
6-Aminoindazole (1.0 g, 7.5 mmol) was mixed with ice (6 g) and water (3.5 mL). The reaction mixture was cooled to 0°C and concentrated aqueous hydrochloride solution (3.8 mL) was added followed by a solution of sodium nitrite (0.6 g, 8.2 mmol) in water (2.5 mL). After 10 min of stirring at 0°C potassium iodide (1.3 g, 9.0 mmol) was added in few portions. Then the cold bath was removed and reaction mixture was warmed to 40°C, heated for 40 min and next the temperature was increased to 50°C and heated for another 30 min. After cooled to ambient temperature the solution was alkalized with 10percent NaOH. The brown precipitate was collected by filtration and washed with saturated aqueous solution of sodium hydrogen carbonate. The crude product was dissolved in tetrahydrofuran (25 mL) and refluxed with silica gel for 10 min. To this slurry hexane was added and the mixture was vaccum filtered through a silica pad. The silica was washed with solution of tetrahydrofuran in hexane (2:3). The filtrate was concentrated under reduced pressure to give 6-iodoindazole (0.9 g). The 6-iodoindazole (0.9 g, 3.9 mmol) was dissolved in dry dichloromethane (30 mL), cooled to 0°C and N- bromosuccinimide (0.8 g, 4.3 mmol) was added in portions. The reaction mixture was stirred at 0°C for lh. The precipitate was collected by filtration and washed with dichloromethane. The obtained product 3-bromo-6-iodo-lH-indazole was used to the next step without further purification. LC-MS (m/z) 324.8 (M+l).
Reference: [1] Patent: EP3127900, 2017, A1, . Location in patent: Paragraph 0250; 0251
[2] Patent: US6531491, 2003, B1,
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180
[4] Patent: US6716837, 2004, B1, . Location in patent: Page column 30
[5] Patent: WO2017/68064, 2017, A1, . Location in patent: Page/Page column 183; 184
  • 2
  • [ 850363-52-9 ]
  • [ 261953-36-0 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With hydrogenchloride In 1,4-dioxane; water at 70℃;
To a solution of step-d product (12 g, 0.04 mol) in 1 ,4-dioxane (60 ml, 5 times), 6N HCI (60 ml, 5 times) was added at rt. Reaction mixture was heated to 7O0C and allowed to stir for 2 hrs at the same temperature. Progress of the reaction was monitored by TLC (30percent ethyl acetate/hexane, Rf-0.5). On completion of the reaction, 1 ,4-dioxane was distilled off completely, residue obtained was basified to a pH-12 -13 with sodium hydroxide solution and the compound extracted with ethyl acetate (2 * 75 ml). Combined extract was dried over sodium sulfate and concentrated under reduced pressure to yield the required product (10 g, 78percent yield).
Reference: [1] Patent: WO2010/127855, 2010, A1, . Location in patent: Page/Page column 121; 122
  • 3
  • [ 83863-33-6 ]
  • [ 261953-36-0 ]
Reference: [1] Patent: US2009/264426, 2009, A1, . Location in patent: Page/Page column 40
[2] Patent: WO2007/29847, 2007, A1, . Location in patent: Page/Page column 59
  • 4
  • [ 7597-18-4 ]
  • [ 261953-36-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180
  • 5
  • [ 261953-36-0 ]
  • [ 319472-78-1 ]
Reference: [1] Patent: WO2006/48745, 2006, A1, . Location in patent: Page/Page column 29
[2] Patent: EP2163544, 2010, A1, . Location in patent: Page/Page column 32
[3] Patent: US2006/94881, 2006, A1, . Location in patent: Page/Page column 22
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