217314-45-9|Methyl 3-amino-5-iodobenzoate| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 217314-45-9 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 217314-45-9 ]

CAS No. :	217314-45-9
Formula :	C₈H₈INO₂
M.W :	277.06
SMILES Code :	O=C(OC)C1=CC(I)=CC(N)=C1
MDL No. :	MFCD08447271
InChI Key :	RFXKJNIWKOHLFF-UHFFFAOYSA-N
Pubchem ID :	11000339

Safety of [ 217314-45-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 217314-45-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	54.84
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.91
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	1.74
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.67
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.	2.21
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	1.94
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.89

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.89
Solubility	0.355 mg/ml ; 0.00128 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.	-2.46
Solubility	0.971 mg/ml ; 0.0035 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	-3.06
Solubility	0.24 mg/ml ; 0.000865 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	No
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.	-6.75 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	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<0.0
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)	1.85

Application In Synthesis of [ 217314-45-9 ]

* 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 [ 217314-45-9 ]

[ 217314-45-9 ] Synthesis Path-Downstream 1~35

1
[ 50765-19-0 ]
[ 217314-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; tin(ll) chloride; In tetrahydrofuran; for 0.5h;Heating / reflux;	Tin chloride (88.6 g, 392 mmol) inEtOH (50mL) was refluxed and the nitrobenzoate from step A (24.1 g, 78.4 mmol) in 1 :1 THF :EtOH (100mL) was added dropwise. The reaction mixture was refluxed for 30 minutes then cooled to 0 C. The resulting solution was basified to pH 8-9 with aq.Na2C03. The aqueous layer was extracted three times with EtOAc (700 mL) and the combined extracts were washed with saturatedNaHC03 then brine. The organics were dried over Na2SO4 and concentrated to afford the desired aniline which was used without further purification.
	With tin(ll) chloride; In tetrahydrofuran; ethanol; for 0.5h;Heating / reflux;	Step B: Tin chloride (88.6 g, 392 mmol) in EtOH (50 mL) was refluxed and the nitrobenzoate from stepA (24.1 g, 78.4 mmol) in 1:1 THF:EtOH (100 mL) was added dropwise. The reaction mixture wasrefluxed for 30 min then cooled to 0 C. The resulting solution was basified to pH 8-9 with aq. Na2CO3.The aqueous layer was extracted three times with EtOAc (700 mL) and the combined extracts werewashed with saturated NaHCOs then brine. The organics were dried over Na2SC>4 and concentrated toafford the crude aniline which was used without further purification.
		Step B: Nitro Reduction; Tin chloride (88.6 g, 392 mmol) in EtOH (50 mL) was refluxed and the nitrobenzoate from step A (24.1 g, 78.4 mmol) in 1:1 THF:EtOH (100 mL).was added dropwise. The reaction mixture was refluxed for 30 minutes then cooled to 0C. The resulting solution was basified to pH 8-9 with aq. Na2C03. The aqueous layer was extracted three times with EtOAc (700 mL) and the combined extracts were washed with saturated NaHC03 then brine. The organics were dried over Na2S04 and concentrated to afford 21.7 g of the crude aniline which was used without further purification.

Step B: Tin chloride (88.6 g, 392 mmol) in ETOH (50 mL) was refluxed and a 1: 1 THF : ETOH (100 mL) solution of the nitrobenzoate from step A (24.1 g, 78.4 mmol) was added dropwise. The reaction mixture was refluxed for 30 minutes then cooled to 0C. The solution was basified to pH 8-9 with aq. NA2CO3. The aqueous layer was extracted with EtOAc (3 x 700 mL). The combined organics were washed with saturated NAHC03 then brine. The organics were dried over NA2S04 AND concentrated affording the crude aniline. LCMS [M + H] = 278.0

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6147 - 6150.
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 641 - 644.
[3]Journal of Medicinal Chemistry,1973,vol. 16,p. 684 - 687.
[4]Patent: WO2005/51914,2005,A1 .Location in patent: Page/Page column 46.
[5]Patent: WO2006/2004,2006,A1 .Location in patent: Page/Page column 39.
[6]Patent: WO2005/103020,2005,A1 .Location in patent: Page/Page column 69.
[7]Patent: WO2005/18545,2005,A2 .Location in patent: Page/Page column 9; 19.

2
[ 217314-45-9 ]
[ 50765-21-4 ]

References: [1]Journal of Medicinal Chemistry,1973,vol. 16,p. 684 - 687.

3
[ 217314-45-9 ]
[ 50765-22-5 ]

References: [1]Journal of Medicinal Chemistry,1973,vol. 16,p. 684 - 687.

4
[ 217314-45-9 ]
[ 110-13-4 ]
[ 217314-42-6 ]

References: [1]Synthesis,1998,p. 1599 - 1603.

5
[ 217314-45-9 ]
[ 124-63-0 ]
[ 847157-47-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 0 - 20℃;	To a0 C solution of aniline from step B (21.7 g, 78.3 mmol) in 3: 1CECl2 : pyridine (75mL) was added methanesulfonyl chloride (6.36mL, 82.2 mmol). The ice bath was removed after 15 minutes and the solution was. stirred overnight at rt. The reaction mixture was extracted several times with INHC1. <Desc/Clms Page number 47>The organic phase was dried, concentrated, and chromatographed (1: 1 EtOAc: Hex) to afford the desired sulfonamide as a white solid.
	With pyridine; In dichloromethane; at 0 - 20℃;	Step C: To a 0C solution of aniline from step B (21.7 g, 78.3 mmol) in 3:1 DCM:pyridine (75 mL) wasadded methanesulfonyl chloride (6.36 mL, 82.2 mmol). The ice bath was removed after 15 min and thesolution was stirred overnight at rt. The reaction mixture was extracted several times with IN HC1. Theorganic phase was dried, concentrated, and cliromatographed (1:1 EtOAc:Hex) to afford the desiredsulfonamide as a white solid.
	With pyridine; In dichloromethane; at 0 - 20℃;	Step C: Mesylation; To a 0 C solution of aniline from step B (21.7 g, 78.3 mmol) in 3:1 1 CH2Cl2: pyridine (75 mL) was added methanesulfonyl chloride (6.36 mL, 82.2 mmol). The ice bath was removed after 15 min and the solution was stirred overnight at rt. The reaction mixture was extracted several times with IN HCI. The organic phase was dried, concentrated, and chromatographed (1:1 EtOAc:Hex) to afford 25.2 g of the desired sulfonamide as a white solid.

With pyridine; In dichloromethane; at 0 - 20℃;

Step C: To a 0C solution of the aniline from step B (21.7 g, 78.3 mmol) in 3: 1 CH2CIZ : PYRIDINE (75 mL) was added methanesulfonyl chloride (6.36 ML, 82.2 mmol). The ice bath was removed after 15 minutes and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc (200 mL), washed 2x IN HC1, and dried over MGSO4. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (1 : 1 EtOAc/Hexanes) to provide he sulfonamide. LCMS [M+] 355. 8. IH NMR (CDC13) 6 8.17 (s, 1H), 7.86 (s, 1H), 7.18 (s, 1H), 3.95 (s, 3H), 3.08 (s, 3H).

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6147 - 6150.
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 641 - 644.
[3]Patent: WO2005/51914,2005,A1 .Location in patent: Page/Page column 46-47.
[4]Patent: WO2006/2004,2006,A1 .Location in patent: Page/Page column 39.
[5]Patent: WO2005/103020,2005,A1 .Location in patent: Page/Page column 69-70.
[6]Patent: WO2005/18545,2005,A2 .Location in patent: Page/Page column 9; 19.

6
[ 217314-45-9 ]
[ 847157-48-6 ]

7
[ 217314-45-9 ]
[ 847157-50-0 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6147 - 6150.
[2]Patent: WO2005/18545,2005,A2 .

8
[ 217314-45-9 ]
[ 847157-49-7 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6147 - 6150.
[2]Patent: WO2005/18545,2005,A2 .

9
[ 217314-45-9 ]
[ 913626-01-4 ]