552331-00-7|4-Iodopyridin-2-amine| Ambeed

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Quality Control of [ 552331-00-7 ] Purity: 95% SDS Specification

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Product Details of [ 552331-00-7 ]

CAS No. :	552331-00-7
Formula :	C₅H₅IN₂
M.W :	220.01
SMILES Code :	NC1=NC=CC(I)=C1
MDL No. :	MFCD09038163
InChI Key :	RSMQQONIFJLFAK-UHFFFAOYSA-N
Pubchem ID :	22607551

Safety of [ 552331-00-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 552331-00-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	41.36
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.52
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	0.85
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.28
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.	1.16
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	1.69
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.29
Solubility	1.12 mg/ml ; 0.00507 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.25
Solubility	12.4 mg/ml ; 0.0562 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.62
Solubility	0.524 mg/ml ; 0.00238 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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	No
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.	-7.04 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	0.0
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	0.0
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<1.0
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)	1.92

Application In Synthesis of [ 552331-00-7 ]

* 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 [ 552331-00-7 ]

[ 552331-00-7 ] Synthesis Path-Downstream 1~41

1
4-iodo-pyridine-2-carbonyl azide [ No CAS ]
[ 552331-00-7 ]

References: [1]Chemische Berichte,1931,vol. 64,p. 21,26.

2
[ 552331-00-7 ]
[ 4637-24-5 ]
N'-(4-iodo-pyridin-2-yl)-N,N-dimethyl-formamidine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627.

3
[ 405939-28-8 ]
[ 552331-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 1h;	To an ice-cold solution of the product from Step A above (3.84 g, 12.0 mmol) in 25 mL of dichloromethane was added trifluoroacetic acid (12 mL) dropwise. The resultant solution was allowed to warm to room temperature and, after 1 h, the volatiles were removed under reduced pressure. The residue was dissolved in water (120 ML), and the solution was neutralized by portionwise addition of sodium bicarbonate. The mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous brine, dried over magnesium sulfate and concentrated to afford an off-white solid, which was triturated with hexanes to afford the title compound as a white powder. MS 221.1 (M+1).

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627.
[2]Patent: WO2004/43940,2004,A1 .Location in patent: Page 85.

4
[ 552331-00-7 ]
[ 690258-25-4 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627.

5
[ 552331-00-7 ]
[2-dimethylcarbamoyl-1-(3-fluoro-pyrrolidine-1-carbonyl)-2-(4-[1,2,4]triazolo[1,5-a]pyridin-7-yl-phenyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627.

6
[ 552331-00-7 ]
[1-(3,3-difluoro-pyrrolidine-1-carbonyl)-2-dimethylcarbamoyl-2-(4-[1,2,4]triazolo[1,5-a]pyridin-7-yl-phenyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627.

7
[ 552331-00-7 ]
(2S,3S)-3-amino-4-[(3S)-3-fluoropyrrolidin-1-yl]-N,N-dimethyl-4-oxo-2-(4-[1,2,4]triazolo[1,5-a]pyridin-7-ylphenyl)butanamide trifluoroacetate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627.

8
[ 552331-00-7 ]
(2S,3S)-3-amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-(4-[1,2,4]triazolo[1,5-a]pyridin-7-ylphenyl)butanamide trifluoroacetate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627.
[2]Patent: WO2004/43940,2004,A1 .

9
[ 552331-00-7 ]
N-(4-iodo-[2]pyridyl)-benzamide [ No CAS ]

References: [1]Chemische Berichte,1931,vol. 64,p. 21,26.

10
[ 552331-00-7 ]
[ 4637-24-5 ]
[ 690258-25-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of the product from Step B above (220 mg, 1.00 mmol) in N, N-dimethylformamide (0.5 ML) was added N, N-dimethylformamide dimethyl acetal (0.37 ML, 2.60 mmol). The reaction mixture was heated to 130 C OVERNIGHT. AFTER cooling to room temperature, the volatiles were removed under reduced pressure to afford a red oil, which was dissolved in 2.0 mL of methanol and 0.162 ML of pyridine. The solution was cooled in an ice bath and hydroxylamine-O-sulfonic acid (147 mg, 1.30 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The volatiles were removed under reduced pressure, and the residue was partitioned between saturated aqueous brine solution and ethyl acetate. The aqueous layer was further extracted with ethyl acetate, and the combined organic layers were washed with saturated aqueous brine solution (100 mL), dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as an orange solid. MS 246.1 (M+1).

References: [1]Patent: WO2004/43940,2004,A1 .Location in patent: Page 85.

11
[ 552331-00-7 ]
[ 24424-99-5 ]
[ 552331-01-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	In tetrahydrofuran;	Example 75B N,N-Bis(tert-butyloxylcarbonyl)amino-4-iodopyridine A solution of the product from Example 75A above (1.0 g, 4.5 mmol) in THF (25 mL) was treated dropwise with 1.0M LiHMDS (9.0 mL, 9.0 mmol), stirred for 30 minutes, treated with di-t-butyl dicarbonate(1.96 g, 9.0 mmol) and stirred for 1 hour. The mixture was quenched with water (10 mL), warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with 1:1 hexanes/ethyl acetate to provide the desired product (1.0 g, 53%). MS (DCI/NH3) m/z 421 (M+H).
53%		Example 75B N,N-Bis(tert-butyloxylcarbonyl)amino-4-iodopyridine A solution of the product from Example 75A above (1.0 g, 4.5 mmol) in THF (25 mL) was treated dropwise with 1.0M LiHMDS (9.0 mL, 9.0 mmol), stirred for 30 minutes, treated with di-t-butyl dicarbonate(1.96 g, 9.0 mmol) and stirred for 1 hour. The mixture was quenched with water (10 mL), warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with 1:1 hexanes/ethyl acetate to provide the desired product (1.0 g, 53%). MS (DCI/NH3) m/z 421 (M+H).

References: [1]Patent: US2003/187026,2003,A1 .
[2]Patent: US2003/199511,2003,A1 .Location in patent: Page/Page column 33.

12
[ 60-35-5 ]
[ 22282-70-8 ]
[ 552331-00-7 ]

Yield	Reaction Conditions	Operation in experiment
37%	With potassium carbonate; In ethyl acetate;	Example 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H).

References: [1]Patent: US2003/187026,2003,A1 .

13
[ 22282-70-8 ]
[ 552331-00-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With ammonium hydroxide; In dimethyl sulfoxide; at 100℃; for 40h;	A mixture of 2-fluoro-4-iodopyridine (10.00g, 43.50mmol), ammonium hydroxide (10mL) in DMSO (20mL) was stirred at 100 C for 40 hours. H2O (100mL) was added to the reaction mixture and the precipitate was filtered to afford the compound 10a as a brown solid (8.62g, 90%). MS: 221 (M+H) +.
90%	With ammonium hydroxide; In dimethyl sulfoxide; at 100℃; for 40h;	A solution of 2-fluoro-4-iodopyridine (10.00 g, 43.50 mmol) and ammonia (10 mL) in DMSO (20 mL) was stirred at 100 C for 40 h.Water (100 mL) was added to the reaction solution, and a solid was precipitated. The brown solid compound 10a (8.62 g, 90%) was obtained by filtration
60%	With ammonia; In water; at 150℃; for 3h;Sealed tube;	Reference Example 2; 4-iodopyridin-2-amine2-Fluoro-4-iodopyridine (11.2 g, 50 mmol) obtained in Reference Example 1 and 28% aqueous ammonia solution (100 ml) were stirred at 150 C. for 3 hr in a sealed tube. The mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate to give the title compound (6.6 g, yield 60%). melting point 167-168 C.1H-NMR (CDCl3) delta: 4.34 (2H, brs), 6.92 (1H, d, J=1.4 Hz), 6.99 (1H, dd, J=5.5, 1.4 Hz), 7.73 (1H, d, J=5.5 Hz).

37%

With acetamide; potassium carbonate; In ethyl acetate; at 180℃; for 7h;

Example 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H).

References: [1]Patent: WO2017/211303,2017,A1 .Location in patent: Page/Page column 43.
[2]Patent: TW2019/25186,2019,A .Location in patent: Paragraph 0147; 0148.
[3]Patent: US2011/39893,2011,A1 .Location in patent: Page/Page column 25.
[4]Patent: US2003/199511,2003,A1 .Location in patent: Page/Page column 33.

14
[ 552331-00-7 ]
[ 103859-86-5 ]
C₁₆H₁₇N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 14h;Inert atmosphere;	Example 20; bis(2,2,2-trichloroethyl)(4-(4-(4-methoxyphenyl)-2-oxopyrrolidin-1-yl)pyridin-2-yl)imidodicarbonateA solution of <strong>[552331-00-7]4-iodopyridin-2-amine</strong> (440 mg, 2 mmol), 4-(4-methoxyphenyl)pyrrolidin-2-one (459 mg, 2.4 mmol) obtained in Reference Example 8, potassium phosphate (552 mg, 4 mmol), copper iodide (76 mg, 0.4 mmol) and N,N'-dimethylethylenediamine (43 mul, 0.4 mmol) in dioxane (10 ml) was stirred at 100 C. for 14 hr under an argon atmosphere. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. To a solution of the obtained residue and triethylamine (0.35 ml, 4.8 mmol) in tetrahydrofuran (20 ml) was added 2,2,2-trichloroethyl chloroformate (0.6 ml, 4.4 mmol) at 0 C., and the mixture was stirred for 10 min. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (100 mg, yield 15%) as a solid.1H-NMR (CDCl3) delta: 2.75-2.87 (1H, m), 2.98-3.10 (1H. m), 3.65-3.77 (1H, m), 3.77-3.85 (1H, m), 3.82 (3H, s), 4.19 (1H, dd, J=9.3, 8.0 Hz), 4.79-4.83 (4H, m), 6.91 (1H, d, J=8.5 Hz), 7.19 (1H, d, J=8.5 Hz), 7.70 (1H, dd, J=5.8, 1.6 Hz), 7.73 (1H, d, J=1.6 Hz), 8.47 (1H, d, J=5.8 Hz).

References: [1]Patent: US2011/39893,2011,A1 .Location in patent: Page/Page column 37.

15
[ 616-45-5 ]
[ 552331-00-7 ]
[ 1019650-76-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 14h;Inert atmosphere;	Reference Example 3; 1-(2-aminopyridin-4-yl)pyrrolidin-2-oneA solution of <strong>[552331-00-7]4-iodopyridin-2-amine</strong> (440 mg, 2 mmol) obtained in Reference Example 2, pyrrolidin-2-one (387 mg, 2.4 mmol), potassium carbonate (553 mg, 4 mmol), copper iodide (76 mg, 0.4 mmol) and N,N'-dimethylethylenediamine (43 mul, 0.4 mmol) in dioxane (10 ml) was stirred at 100 C. for 14 hr under an argon atmosphere. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. The residue was crystallized from ethanol to give the title compound (160 mg, yield 45%).1H-NMR (CDCl3) delta: 2.17 (2H, tt, J=7.8, 6.9 Hz), 2.62 (2H, t, J=7.8 Hz), 3.82 (2H, t, J=6.9 Hz), 4.44 (2H, brs), 6.78 (1H, d, J=5.8, 1.9 Hz), 7.09 (1H, d, J=1.9 Hz), 8.01 (1H, d, J=5.8 Hz).

References: [1]Patent: US2011/39893,2011,A1 .Location in patent: Page/Page column 25.

16
[ 372-48-5 ]
[ 552331-00-7 ]