660-49-1|3-Fluoro-5-iodoaniline| Ambeed

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Quality Control of [ 660-49-1 ] Purity: 97% SDS Specification

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Product Details of [ 660-49-1 ]

CAS No. :	660-49-1
Formula :	C₆H₅FIN
M.W :	237.01
SMILES Code :	NC1=CC(F)=CC(I)=C1
MDL No. :	MFCD04116466

Safety of [ 660-49-1 ]

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

Computational Chemistry of [ 660-49-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
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	43.52
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.69
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	1.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.44
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.	2.84
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	2.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.06
Solubility	0.208 mg/ml ; 0.000878 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.	-2.16
Solubility	1.63 mg/ml ; 0.00688 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.27
Solubility	0.126 mg/ml ; 0.000532 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.	-6.33 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	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	2.0 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)	2.08

Application In Synthesis of [ 660-49-1 ]

* 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 [ 660-49-1 ]

[ 660-49-1 ] Synthesis Path-Downstream 1~25

1
[ 3819-88-3 ]
[ 660-49-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tin(II) chloride dihdyrate; In ethanol; for 1.5h;Reflux;	Example 2Synthesis of 3-fluoro-5-iodo-N,N-dimethylaniline (VMY-2-119): The suspension of l-fluoro-3-iodo-5 -nitrobenzene (0.5 g, 1.87 mmol) and SnCl2'2H20 (1.5 g, 6.64 mmol) in EtOH (10 mL) was heated to reflux for 1.5 h. The solvent was removed and the crude mixture was diluted with ether, washed with 4 N NaOH and brine. The ether layer was- 42 -B4067289v2 separated and dried over Na2S04, filtered, concentrated to yield amine compound as a solid (0.4 g, 91%). The crude product was used without purification.A solution of above amine (0.4 g, 1.69 mmol) and iodomethane (0.719 g, 5 mmol) in dimethylformamide (DMF; 10 mL) containing potassium carbonate (0.46 g, 3.38 mmol) was stirred for 48 h at room temperature. Water (lOmL) was then added and the solution was extracted with ether three times. The organic extracts washed with water, brine, dried over Na2S04, filtered and concentrated. The crude product was purified by column chromatography to yield VMY-2-119 as a liquid (0.23 g, 52%). 1H NMR (399 MHz) ? 6.69 - 6.63 (m, 2H), 6.22 (dt, J = 12.5, 2.3, 1H), 2.83 (s, 6H). 13C NMR (100 MHz) ? 163.33(d, JF-C=245 Hz), 152.49(d, J=l lHz) 116.91 (d, J = 2.4), 112.12(d, J=24 Hz), 98.73(d, J=26Hz), 94.24(d, J=l l Hz), 40.21 (s, 3H).
		Production Example 341 3-Fluoro-5-iodophenylamine 3.2 g crude title compound (yellow oil) was obtained from 3.0 g of 3-fluoro-5-iodonitrobenzene by the same reaction as in Production Example 335.1H-NMR (CDCl3) delta: 3.78(brs, 2H), 6.28-6.35(m, 1H), 6.75-6.84(m, 2H)
	With iron; acetic acid; In tetrahydrofuran; water; at 40℃;	3-Iodo-5-fluoro-1-nitrobenzene (5.2 g; 19.48 mmol) is dissolved in a 4/3 water/tetrahydrofuran mixture. Powdered iron (8.7 g; 156 mmol), followed by acetic acid (4.5 ml) are added at room temperature and the suspension formed is stirred overnight at 40 C. The reaction mixture is filtered over diatomaceous earth and poured on to water. The mixture is extracted with ethyl acetate and the combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexane/ethyl acetate (3/1). The pure fractions are combined and the solvent is evaporated off. The residue is diluted with methylene chloride (30 ml), and pyridine (4,0 ml; 49.5 mmol) and trifluoroacetic anhydride (3.44 ml; 24.7 mmol) are added and the mixture is stirred for one hour at room temperature. The reaction solution is poured on to aqueous hydrochloric acid (1 M; 50 ml) and the mixture is extracted twice with ethyl acetate (50 ml). The combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexanelethyl acetate (9/1). The pure fractions are combined and the solvent is evaporated off. [00367] Yield: 5.40 g (98%) as a white solid. [00368] MS: 333 (M)

References: [1]Patent: WO2013/71067,2013,A1 .Location in patent: Page/Page column 42-43.
[2]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163.
[3]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348.
[4]Patent: EP1382603,2004,A1 .Location in patent: Page 170.
[5]Patent: US6821980,2004,B1 .Location in patent: Page column 40-41.
[6]Journal of Medicinal Chemistry,2013,vol. 56,p. 8404 - 8421.

2
[ 660-49-1 ]
[ 821-48-7 ]
[ 852807-42-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163.

3
[ 660-49-1 ]
(E)-3-[4-(3-fluoro-5-iodophenyl)piperazin-1-yl]-1-[5-methyl-1-(pyrimidin-2-yl)-1H-pyrazol-4-yl]prop-1-ene [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163.

4
[ 660-49-1 ]
[ 1027953-88-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163.

5
[ 660-49-1 ]
3-[4-(3-fluoro-5-iodo-phenyl)-piperazin-1-yl]-1-(5-methyl-1-pyrimidin-2-yl-1<i>H</i>-pyrazol-4-yl)-propan-1-ol [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163.

6
[ 99-65-0 ]
[ 660-49-1 ]

References: [1]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348.

7
[ 10394-64-6 ]
[ 660-49-1 ]

References: [1]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348.

8
[ 6276-04-6 ]
[ 660-49-1 ]

References: [1]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348.

9
5-Iod-3-nitro-1-diazonio-benzol [ No CAS ]
[ 660-49-1 ]

References: [1]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348.

10
[ 660-49-1 ]
[ 124-63-0 ]
[ 710348-26-8 ]

Yield	Reaction Conditions	Operation in experiment
78%		Dissolve <strong>[660-49-1]3-fluoro-5-iodoaniline</strong> (600mg, 2. 53MMOL) (prepared as described in published PCT International Application W096/23783 A1, published August 8,1996), METHANESULFONYL chloride (896mg, 7. 83MMOL), triethylamine (1. 91G, 18.9mmol), and N, N-dimethylamino-4-pyridine (31MG, 0. 253MMOL) in CH2CK (lOmL) and stir at room temperature overnight. Dilute with L. OON aqueous HC1 (20ML) and extract into ethyl acetate. Dry (MGS04) and concentrate organics to a yellow solid. Dissolve solid in THF (50ML) and add L. OM tetrabutylammonium fluoride (2.8mL). Heat to reflux for 3. 5h. Cool to room temperature, dilute with H20, and extract into ethyl acetate. Dry (MGS04) and concentrate organics. Chromatograph on silica gel (40g), eluting with 20% to 35% ethyl acetate/hexanes affords 618MG (78%) of the title compound as a white solid. MS (ES) 314 (M-H) ; HPLC shows 100% purity.

References: [1]Patent: WO2004/52847,2004,A2 .Location in patent: Page 172.

11
[ 660-49-1 ]
[ 407-25-0 ]
[ 338454-90-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine; In dichloromethane; at 20℃; for 1h;	3-Iodo-5-fluoro-1-nitrobenzene (5.2 g; 19.48 mmol) is dissolved in a 4/3 water/tetrahydrofuran mixture. Powdered iron (8.7 g; 156 mmol), followed by acetic acid (4.5 ml) are added at room temperature and the suspension formed is stirred overnight at 40 C. The reaction mixture is filtered over diatomaceous earth and poured on to water. The mixture is extracted with ethyl acetate and the combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexane/ethyl acetate (3/1). The pure fractions are combined and the solvent is evaporated off. The residue is diluted with methylene chloride (30 ml), and pyridine (4,0 ml; 49.5 mmol) and trifluoroacetic anhydride (3.44 ml; 24.7 mmol) are added and the mixture is stirred for one hour at room temperature. The reaction solution is poured on to aqueous hydrochloric acid (1 M; 50 ml) and the mixture is extracted twice with ethyl acetate (50 ml). The combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexanelethyl acetate (9/1). The pure fractions are combined and the solvent is evaporated off. [00367] Yield: 5.40 g (98%) as a white solid. [00368] MS: 333 (M)

References: [1]Patent: US6821980,2004,B1 .Location in patent: Page column 40-41.

12
[ 660-49-1 ]
[ 474710-11-7 ]

Yield	Reaction Conditions	Operation in experiment
		Production Example 342 benzhydrylidene-(3-fluoro-5-iodophenyl)-amine 0.75 g of the title compound (yellow oil) was obtained from 3.2 g of <strong>[660-49-1]3-fluoro-5-iodophenylamine</strong> (compound in Production Example 341) by the same reaction as in Production Example 336.1H-NMR (CDCl3) delta: 6.36-6.43(m, 1H), 6.86-6.92(m, 1H), 6.96-7.02(m, 1H), 7.08-7.16(m, 2H), 7.28-7.54(m, 6H), 7.68-7.76(m, 2H)

References: [1]Patent: EP1382603,2004,A1 .Location in patent: Page 170; 171.

13
[ 660-49-1 ]
[ 74-88-4 ]
[ 1369808-80-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 48h;	Example 2Synthesis of 3-fluoro-5-iodo-N,N-dimethylaniline (VMY-2-119): The suspension of l-fluoro-3-iodo-5 -nitrobenzene (0.5 g, 1.87 mmol) and SnCl2'2H20 (1.5 g, 6.64 mmol) in EtOH (10 mL) was heated to reflux for 1.5 h. The solvent was removed and the crude mixture was diluted with ether, washed with 4 N NaOH and brine. The ether layer was- 42 -B4067289v2 separated and dried over Na2S04, filtered, concentrated to yield amine compound as a solid (0.4 g, 91%). The crude product was used without purification.A solution of above amine (0.4 g, 1.69 mmol) and iodomethane (0.719 g, 5 mmol) in dimethylformamide (DMF; 10 mL) containing potassium carbonate (0.46 g, 3.38 mmol) was stirred for 48 h at room temperature. Water (lOmL) was then added and the solution was extracted with ether three times. The organic extracts washed with water, brine, dried over Na2S04, filtered and concentrated. The crude product was purified by column chromatography to yield VMY-2-119 as a liquid (0.23 g, 52%). 1H NMR (399 MHz) ? 6.69 - 6.63 (m, 2H), 6.22 (dt, J = 12.5, 2.3, 1H), 2.83 (s, 6H). 13C NMR (100 MHz) ? 163.33(d, JF-C=245 Hz), 152.49(d, J=l lHz) 116.91 (d, J = 2.4), 112.12(d, J=24 Hz), 98.73(d, J=26Hz), 94.24(d, J=l l Hz), 40.21 (s, 3H).

References: [1]Patent: WO2013/71067,2013,A1 .Location in patent: Page/Page column 42-43.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 8404 - 8421.

14
[ 660-49-1 ]
C₁₇H₂₁FINO₄ [ No CAS ]