191980-54-8|4-Iodo-1-trityl-1H-pyrazole| Ambeed

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Quality Control of [ 191980-54-8 ] Purity: 95% SDS Specification

COA

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NMR

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Product Details of [ 191980-54-8 ]

CAS No. :	191980-54-8
Formula :	C₂₂H₁₇IN₂
M.W :	436.29
SMILES Code :	IC1=CN(N=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
MDL No. :	MFCD23135653
InChI Key :	UJEYQAFIQWSUOR-UHFFFAOYSA-N
Pubchem ID :	15324479

Safety of [ 191980-54-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 191980-54-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	25
Num. arom. heavy atoms	23
Fraction Csp3	0.05
Num. rotatable bonds	4
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	109.55
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.51
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	5.66
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.33
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	5.0
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	5.3
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.96

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.53
Solubility	0.000129 mg/ml ; 0.000000297 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-5.8
Solubility	0.000693 mg/ml ; 0.00000159 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-8.85
Solubility	0.000000621 mg/ml ; 0.0000000014 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.94 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.05

Application In Synthesis of [ 191980-54-8 ]

* 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.

Downstream synthetic route of [ 191980-54-8 ]

[ 191980-54-8 ] Synthesis Path-Downstream 1~35

1
[ 3469-69-0 ]
[ 76-83-5 ]
[ 191980-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	1-Trityl-4-iodopyrazole The title compound was prepared by combining 4-iodopyrazole (10 g, 52 mmol), triphenylmethyl chloride (14.4 g, 51.6 mmol), triethylamine (NEt3) (7.2 mL, 52 mmol), and DMF (80 mL). After stirring overnight, the mixture was poured onto ice water. The precipitated solid was collected and recrystallized to give the title compound as a solid, mp 193-194 C. 1H NMR (CDCl3): delta7.11 (m, 6 H), 7.32 (m, 9 H), 7.41 (s, 1 H), 7.67 (s, 1 H).
	With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃;	4-Iodopyrazole (2.5 g, 1 equiv.) was dissolved in dry DMF (20 mL), and TEA (1.8 mL, 1 equiv.) was added at 0 C. Then, trityl chloride (3.56 g, 0.99 equiv.) was added, and the reaction mixture was stirred at 0 C to RT overnight. The mixture was then poured into ice water (250 mL) and was filtered. The obtained solid was washed with water (150 mL), and was then triturated with toluene (20 mL) and dried under vacuum to afford the expected product (3.48 g), which was used in the next reaction step without further purification.
	With triethylamine; In N,N-dimethyl-formamide; at 20℃;	Compound 36a (1000 mg, 5.15 mmol)And Et3N (1040 mg, 10.3 mmol) was dissolved in 20 mL DMF.Then TrtCl (1720 mg, 6.18 mmol) was added.The reaction was carried out at room temperature overnight, and purified by silica gel column chromatography to afford Compound 36b.

References: [1]Chemical Communications,2019,vol. 55,p. 9387 - 9390.
[2]Synthesis,1997,p. 563 - 566.
[3]Bioorganic and medicinal chemistry,2001,vol. 9,p. 3243 - 3253.
[4]Patent: US2015/329492,2015,A1 .Location in patent: Sheet 1/5.
[5]Journal of the American Chemical Society,2018,vol. 140,p. 6383 - 6390.
[6]MedChemComm,2014,vol. 5,p. 72 - 81.
[7]Patent: US6528510,2003,B1 .
[8]Patent: WO2019/43372,2019,A1 .Location in patent: Page/Page column 103.
[9]Patent: CN109928979,2019,A .Location in patent: Paragraph 0285-0288.

2
[ 191980-51-5 ]
[ 191980-54-8 ]
4-(1-Trityl-1H-pyrazol-4-yl)-phenylamine [ No CAS ]

References: [1]Synthesis,1997,p. 563 - 566.

3
[ 79048-32-1 ]
[ 191980-54-8 ]
4-(4-Nitro-phenyl)-1-trityl-1H-pyrazole [ No CAS ]

References: [1]Synthesis,1997,p. 563 - 566.

4
4-(tributylstannyl)phenol [ No CAS ]
[ 191980-54-8 ]
[ 191980-59-3 ]

References: [1]Synthesis,1997,p. 563 - 566.

5
[ 191980-54-8 ]
[ 149524-45-8 ]
[ 398152-64-2 ]

References: [1]Bioorganic and medicinal chemistry,2001,vol. 9,p. 3243 - 3253.

6
[ 191980-54-8 ]
[ 188975-86-2 ]
[ 398152-64-2 ]

References: [1]Bioorganic and medicinal chemistry,2001,vol. 9,p. 3243 - 3253.

7
[ 105-07-7 ]
[ 191980-54-8 ]
[ 466671-49-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 937 - 941.

8
phenylmagnesium bromide [ No CAS ]
[ 191980-54-8 ]
[ 919802-97-4 ]

References: [1]Heterocycles,2006,vol. 68,p. 2247 - 2252.

9
[ 916493-46-4 ]
[ 191980-54-8 ]
Methyl (S)-{2,3,9-trimethyl-4-[4-(1H-pyrazol-4-yl)phenyl]-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl}acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 95: Methyl (S)-{2,3,9-trimethyl-4-[4-(1H-pyrazol-4-yl)phenyl]-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl}acetate To a mixture of the compound described in Starting Material Synthetic Example 1 (420 mg), tetrakistriphenylphosphine palladium"(58 mg) and <strong>[191980-54-8]4-iodo-1-trityl-1H-pyrazole</strong> (654 mg) were added tetrahydrofuran (1.5 mL) and 2 M aqueous sodium carbonate solution (1.5 mL), and the mixture was stirred at 100C for 4 hr. After cooling, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol=100:1) to give compound (729 mg). The obtained compound (729 mg) was dissolved in methanol (3 mL). Trifluoroacetic acid (154 muL) was added, and the mixture was stirred at room temperature for 2 days. After completion of the reaction, the mixture was neutralized with aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol=100:1) to give the title compound (162 mg) . 1H-NMR (400 MHz, DMSO-d6) delta: 2.67 (3H, s), 2.43 (3H, s), 2.62 (3H, s), 3.39-3.52 (2H, m), 3.68 (3H, s), 4.49 (1H, t, J = 7.2 Hz), 7.39 (2H, d, J = 8.2 Hz), 7.65 (2H, d, J = 8.2 Hz), 8.11 (2H, brs) MS (ESI) m/z: 447 (M+H)+.

References: [1]Patent: EP1887008,2008,A1 .Location in patent: Page/Page column 51.

10
[ 191980-54-8 ]
[ 466671-50-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 937 - 941.

11
[ 191980-54-8 ]
1-(3,5-dichloro-phenyl)-3-[4-(1-trityl-1<i>H</i>-pyrazol-4-ylmethyl)-benzyl]-urea [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 937 - 941.

12
[ 191980-54-8 ]
[ 466671-51-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 937 - 941.

13
[ 102-54-5 ]
[ 191980-54-8 ]
[ 936484-37-6 ]

References: [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 1834 - 1844.

14
[ 98-91-9 ]
[ 191980-54-8 ]
[ 1269071-49-9 ]

Yield	Reaction Conditions	Operation in experiment
3.88 g	With copper(l) iodide; 1,10-Phenanthroline; N-ethyl-N,N-diisopropylamine; In toluene; for 16h;Inert atmosphere; Reflux;	To a solution of 4-iodo-l-trityl-pyrazole (3.48 g, 1 equiv.), thiobenzoic acid (1.12 mL, 1.2 equiv.), 1, 10-phenantroline (0.22 mL, 0.2 equiv.) and D/PEA (2.78 mL, 2 equiv.) in toluene (16 mL) was added Cul (0.15 g, 0.1 equiv.). The resulting mixture was degassed and then stirred under argon at reflux temperature for 16 h. The reaction mixture was filtered through a pad of Celite, and the pad was washed with toluene. The solvent was removed under vacuum, and the crude product was purified by flash chromatography on silica gel (eluting with a cyclohexane/EtOAc gradient, 0-10 % of EtOAc) to afford the expected product (3.88 g).

References: [1]Tetrahedron Letters,2011,vol. 52,p. 820 - 823.
[2]Patent: WO2019/43372,2019,A1 .Location in patent: Page/Page column 104.

15
[ 191980-54-8 ]
[ 1269071-57-9 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 820 - 823.
[2]Patent: WO2019/43372,2019,A1 .

16
[ 191980-54-8 ]
[ 1269071-74-0 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 820 - 823.

17
[ 191980-54-8 ]
[ 1269071-75-1 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 820 - 823.

18
[ 766-98-3 ]
[ 191980-54-8 ]
[ 1242028-50-7 ]

References: [1]Heterocycles,2010,vol. 81,p. 1651 - 1659.

19
[ 629-05-0 ]
[ 191980-54-8 ]
[ 1242028-47-2 ]

References: [1]Heterocycles,2010,vol. 81,p. 1651 - 1659.

20
[ 107-19-7 ]
[ 191980-54-8 ]
[ 1242028-45-0 ]

References: [1]Heterocycles,2010,vol. 81,p. 1651 - 1659.
[2]MedChemComm,2014,vol. 5,p. 72 - 81.

21
[ 536-74-3 ]
[ 191980-54-8 ]
[ 1242028-48-3 ]

References: [1]Heterocycles,2010,vol. 81,p. 1651 - 1659.

22
[ 768-60-5 ]
[ 191980-54-8 ]
[ 1242028-51-8 ]

References: [1]Heterocycles,2010,vol. 81,p. 1651 - 1659.

23
[ 191980-54-8 ]
[ 1066-54-2 ]
[ 1242028-46-1 ]

References: [1]Heterocycles,2010,vol. 81,p. 1651 - 1659.
[2]Journal of the American Chemical Society,2018,vol. 140,p. 6014 - 6026.

24
[ 100-69-6 ]
[ 191980-54-8 ]
[ 1310452-63-1 ]