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[ CAS No. 290368-00-2 ] {[proInfo.proName]}

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Chemical Structure| 290368-00-2
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Product Details of [ 290368-00-2 ]

CAS No. :290368-00-2 MDL No. :MFCD09835520
Formula : C12H13IN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DHNSGIOEVGLLOI-UHFFFAOYSA-N
M.W : 344.15 Pubchem ID :11473390
Synonyms :

Calculated chemistry of [ 290368-00-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 74.65
TPSA : 44.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.02
Log Po/w (XLOGP3) : 3.53
Log Po/w (WLOGP) : 3.42
Log Po/w (MLOGP) : 3.39
Log Po/w (SILICOS-IT) : 2.49
Consensus Log Po/w : 3.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.39
Solubility : 0.014 mg/ml ; 0.0000406 mol/l
Class : Moderately soluble
Log S (Ali) : -4.14
Solubility : 0.0249 mg/ml ; 0.0000723 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.9
Solubility : 0.0434 mg/ml ; 0.000126 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.82

Safety of [ 290368-00-2 ]

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 [ 290368-00-2 ]

* 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 [ 290368-00-2 ]
  • Downstream synthetic route of [ 290368-00-2 ]

[ 290368-00-2 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
100% Sonication A mixture of 3-iodo-1H-indazole (0.2 g, 0.82 mmol), ditert-butyldicarbonate (0.2 g, 0.92 mmol) and triethylamine (1 mL) were put under ultrasonic irradiation for 10 min. The resulted solution was neutralized using HCl 1M and then extracted with dichloromethane (3 × 30 mL). The combined organic layers were dried with anhydrous sodium sulfate and removal of the solvent under vacuum afforded a pure product as a pale yellow crystals.Yield: 100percent; m.p.: 93–95 °C; IR (KBr) ν (cm−1): 1728 (C=O); 1150 (C-O); 424 (C-I). 1H-NMR (CDCl3) δ(ppm): 8.09 (1H, d, J = 8.5 Hz, H-7); 7.55 (1H, t, J = 7.8 Hz, H-4); 7.46 (1H, d, J = 7.9 Hz, H-6); 7.33 (1H,t, J = 7.6 Hz, H-5); 1.71 (9H, s, CH3). 13C-NMR δ (ppm): 148.35; 139.59; 130.17; 129.98; 124.21; 121.96;114.56; 102.95; 85.48; 28.18; HRMS calculated for C12H13IN2O2: 344.0022, Found: 344.0016.tert-Butyl 3-iodo-5-nitro-1H-indazole-1-carboxylate (2b). Prepared from 3-iodo-5-nitro-1H-indazole (0.2g, 0.69 mmol), di-tert-butyldicarbonate (0.17 g, 0.78 mmol) and triethylamine (1 mL) to give 0.27 g ofa pale yellow solid. Yield: 100percent; m.p.: 144–145 °C; IR (KBr) ν (cm−1): 1744 (C=O); 1528 (NO2tert-Butyl 3-iodo-1H-indazole-1-carboxylate (2a). A mixture of 3-iodo-1H-indazole (0.2 g, 0.82 mmol),di-tert-butyldicarbonate (0.2 g, 0.92 mmol) and triethylamine (1 mL) were put under ultrasonicirradiation for 10 min. The resulted solution was neutralized using HCl 1M and then extractedwith dichloromethane (3 30 mL). The combined organic layers were dried with anhydrous sodiumsulfate and removal of the solvent under vacuum afforded a pure product as a pale yellow crystals.Yield: 100percent; m.p.: 93–95 °C; IR (KBr) (cm1): 1728 (C=O); 1150 (C-O); 424 (C-I). 1H-NMR (CDCl3) (ppm): 8.09 (1H, d, J = 8.5 Hz, H-7); 7.55 (1H, t, J = 7.8 Hz, H-4); 7.46 (1H, d, J = 7.9 Hz, H-6); 7.33 (1H,t, J = 7.6 Hz, H-5); 1.71 (9H, s, CH3). 13C-NMR (ppm): 148.35; 139.59; 130.17; 129.98; 124.21; 121.96;114.56; 102.95; 85.48; 28.18; HRMS calculated for C12H13IN2O2: 344.0022, Found: 344.0016.
97.5% With sodium hydroxide In acetonitrile at 25℃; for 12 h; tert-butyl 3-iodo-1 H-indazole-1-carboxylate
[00447] To a mixture of 3-iodo-1H-indazole (8 g, 32.7 mmol) and Boc2O (8.6 g, 39.2mmol) in MeCN (100 mL) was added NaOH (2.0 g, 49.1 mmol) at 25 °C and the mixture was stirred for 12 h. The mixture was poured into water (150 mL), extracted with EA (50 mLx2), andthe combined organic phase was washed with saturated brine (200 mLx2), dried with anhydrousNa2S04 and concentrated under vacuum. The residue was purified by silica gel chromatographyto afford the title compound (11.2 g, 97.5percent) as a white solid. MS (m/z): 477.2 [M+1]+.
97.5% With sodium hydroxide In acetonitrile at 25℃; [390j To a mixture of 3-iodo-1H-indazole (8 g, 32.7 mmol) and Boc2O (8.6 g, 39.2 mmoi) inMeCN (100 mL) was added NaOH (2.0 g, 49,1 mmoi) at 25 °C and the mixture was stirred for12 h. The mixture was poured into water (1 50 mL), extracted with EA (50 mL*2), and the combined organic phase was washed with saturated brine (200 mL*2), dried with anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by silica gel chromatography to afford the title compound (11.2 g, 97.5percent) as white solid.
93% at 20℃; 3-Iodo-1H-indazole (S1, 5.00 g, 19.5 mmol) was placed in a round-bottom flask and dissolved in tetrahydrofuran (100 mL). 4-Dimethylaminopyridine (0.24 g, 1.9 mmol, 0.1 equiv) was then added, followed by di-tert-butyl dicarbonate (5.4 mL, 24 mmol, 1.2 equiv). Triethylamine (5.4 mL, 39 mmol, 2.0 equiv) was slowly added to the clear, brown solution by syringe. The resulting solution was stirred at room temperature until it was complete as determined by TLC. The reaction was then diluted with water (75 mL) and ethyl acetate (50 mL). After separating the layers, the aqueous phase was extracted with additional ethyl acetate (3 × 50 mL). The combined organic layers were washed with brine (100 mL), then shaken over magnesium sulfate, filtered, and concentrated under reduced pressure to give the crude product. This material was purified by column chromatography over silica gel (hexanes/ethyl acetate: 100/0 to 90/10) to give the title compound as an orange solid (6.20 g, 93percent).
93% With dmap; triethylamine In tetrahydrofuran at 20℃; for 2 h; Example 2.1. Pre ration of tert-butyl 3-iodo-lH-indazole-l-carboxylate [00283] 3-Iodo-lH-indazole (5.00 g, 19.5 mmol) was placed in a round-bottom flask and dissolved in tetrahydrofuran (100 ml). 4-Dimethylaminopyridine (0.24 g, 1.9 mmol, 0.1 equiv) was then added, followed by di-iert-butyl dicarbonate (5.4 ml, 24 mmol, 1.2 equiv). Triethylamine (5.4 ml, 39 mmol, 2.0 equiv) was slowly added to the clear brown solution by syringe. The resulting solution was stirred at room temperature and monitored by TLC until complete. The reaction required approximately 2 hours. Once complete, the reaction was diluted with water (75 ml) and ethyl acetate (50 ml). After separating the layers, the aqueous phase was extracted with additional ethyl acetate (3 x 50 ml). The combined organic layers were washed with brine (100 ml), shaken over magnesium sulfate, filtered, and concentrated under reduced pressure to give a dark red oil (8.40 g). The crude material was purified by column chromatography over silica gel (hexanes/ethyl acetate: 100/0 to 90/10) to give the title compound as an orange solid (6.20 g, 93percent). 1H NMR (300 MHz, CDC13): δ 8.12 (d, J = 8.4 Hz, 1H), 7.59 (t, J = 7.7 Hz, 1H), 7.50 (d, J = 7.9 Hz, 1H), 7.37 (t, J = 7.5 Hz, 1H), 1.73 (s, 9H); 13C NMR (75 MHz, CDC13): δ 148.3, 139.6, 130.2, 129.9, 124.1, 121.9, 114.5, 102.8, 85.4, 28.1; ESI-MS (M-C4H9): m/z 288.
7 g With dmap In acetonitrile at 0 - 20℃; for 16 h; DMAP (16.37mmoI) was added to Intermediate-71(39 mmcl) in acetonitrile (50m1). The reaction mixture was then cooled to 0°C. BOC anhydride (39.9mmol) was added to the cooled reaction mixture. The reaction was carried out at room temperature for 16 hours. Then the reaction mixture was diluted with water (lOOmI) and extracted with ethyl acetate. Theorganic layer was dried over anhydrous Na2SO4 and evaporated to obtain ntermediate-72 (7g, pale yellow sofld).
7 g With dmap In acetonitrile at 20℃; for 16 h; Synthesis of tert-butyl 3-iodo-1H-indazole-1-carboxylate (Intermediate-72)
DMAP (16.37 mmol) was added to Intermediate-71(39 mmol) in acetonitrile (50 ml).
The reaction mixture was then cooled to 0° C. BOC anhydride (39.9 mmol) was added to the cooled reaction mixture.
The reaction was carried out at room temperature for 16 hours.
Then the reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate.
The organic layer was dried over anhydrous Na2SO4 and evaporated to obtain Intermediate-72 (7 g, pale yellow solid).

Reference: [1] Molecules, 2018, vol. 23, # 8,
[2] Patent: WO2015/58140, 2015, A1, . Location in patent: Paragraph 00447
[3] Patent: WO2016/58544, 2016, A1, . Location in patent: Paragraph 389; 390
[4] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1501 - 1507
[5] Patent: WO2014/47662, 2014, A2, . Location in patent: Paragraph 00283
[6] Journal of Medicinal Chemistry, 2008, vol. 51, # 12, p. 3460 - 3465
[7] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6206 - 6214
[8] Tetrahedron Letters, 2000, vol. 41, # 22, p. 4363 - 4366
[9] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5129 - 5136
[10] Tetrahedron Letters, 2002, vol. 43, # 15, p. 2695 - 2697
[11] Patent: US2010/29733, 2010, A1, . Location in patent: Page/Page column 38
[12] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 23, p. 6998 - 7003
[13] Journal of Medicinal Chemistry, 2010, vol. 53, # 23, p. 8368 - 8375
[14] Patent: WO2013/128465, 2013, A1, . Location in patent: Page/Page column 146
[15] Patent: US2015/158860, 2015, A1, . Location in patent: Paragraph 0520
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Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 22, p. 4363 - 4366
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1852 - 1856
[3] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5129 - 5136
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6206 - 6214
[5] Patent: WO2013/128465, 2013, A1,
[6] Patent: US2015/158860, 2015, A1,
[7] Patent: WO2015/58140, 2015, A1,
[8] Patent: WO2016/58544, 2016, A1,
[9] Molecules, 2018, vol. 23, # 8,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1852 - 1856
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