108499-32-7|Methyl 5-(bromomethyl)thiophene-2-carboxylate| Ambeed

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Structure of 108499-32-7

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Quality Control of [ 108499-32-7 ] Purity: 95% SDS Specification

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Product Details of [ 108499-32-7 ]

CAS No. :	108499-32-7
Formula :	C₇H₇BrO₂S
M.W :	235.10
SMILES Code :	O=C(C1=CC=C(CBr)S1)OC
MDL No. :	MFCD09834150
InChI Key :	GFOPHLFSDVVYGB-UHFFFAOYSA-N
Pubchem ID :	11424851

Safety of [ 108499-32-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Computational Chemistry of [ 108499-32-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.29
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	48.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.37
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	2.38
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.28
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.	1.75
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	3.36
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.43

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.94
Solubility	0.273 mg/ml ; 0.00116 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.	-3.17
Solubility	0.16 mg/ml ; 0.000682 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	-3.01
Solubility	0.231 mg/ml ; 0.000984 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.	-6.04 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)	2.7

Application In Synthesis of [ 108499-32-7 ]

* 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 [ 108499-32-7 ]

[ 108499-32-7 ] Synthesis Path-Downstream 1~54

1
[ 17329-24-7 ]
[ 108499-32-7 ]
[ 133446-64-7 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

2
[ 108499-32-7 ]
[ 133446-73-8 ]
[ 133446-76-1 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

3
[ 108499-32-7 ]
[ 133446-74-9 ]
[ 133446-78-3 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

4
[ 108499-32-7 ]
[ 133446-75-0 ]
[ 133446-80-7 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

5
[ 19432-69-0 ]
[ 108499-32-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Bromosuccinimide; dibenzoyl peroxide; In chloroform; for 7h;Reflux;	Add freshly recrystallised NBS (323.8 g, 1.81 mol) to a solution of methyl-5- methylthiophene-2-carboxylate (258 g, 1.65 mol) in chloroform (2.6 L) at room temperature, and stir. Add benzoyl peroxide (3.99 g, 0.016 mol) and heat the reaction mixture to reflux for 7 hours. Cool the reaction mixture to ambient temperature and filter through diatomaceous earth. Wash the filter cake with chloroform (250 ml). Collect the organic layers and remove the solvent to give the title compound (388 g, 100%), which is used without further purification. ESI (m/z) 236(M+H).
90%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 2h;	A mixture of compound 26.1, NBS (6.26 g, 35.2 mmol) and AIBN (0.03 g, 0.18 mmol) in CCl4 (20 mL) was heated to 8O0C for 2 hours, then cooled to room temperature, filtered, washed with cold CH2Cl2 / CCl4 (1 :1). The filtrate was concentrated to provide compound 26.2 as major product (90%) and was used in the next step without purification.
85%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 2h;	To a stirred solution of compound 20 (2.50 g, 17.58 mmol) in MeOH (30.00 mL) cooled to 0 C, SOCl2 (5.11 mL, 7.32 mmol) was added and the reaction was stirred at 25 C for 12 h. A 2 N solution of NaOH was added and volatiles were removed under reduced pressure. The aqueous phase was extracted with DCM (3 x 25.00 mL) and the combined organic layers were dried over Na2SO4, filtered and evaporated. Methyl 5-methylthiophene-2-carboxylate was obtained in quantitative yield without any further purification. ESI-MS m/z 179 [M+Na]+; 1H NMR (300 MHz, CDCl3) delta 2.51 (s, 3H), 3.84 (s, 3H), 6.75 (d, J =3.1 Hz, 1H), 7.60 (d, J = 3.1 Hz, 1H). To a solution of the previously synthesized ester (3.00 g, 16.85 mmol) in CCl4 (15.00 mL), N-bromosuccinimide (2.70 g, 15.17 mmol)and azobisisobutyronitrile (catalytic amount) were added, and the reaction was stirred at 80 C for 2 h. The reaction was cooled to 25 C and filtered on asmall plug of Celite. Volatiles were removed under reduced pressure and the crude was purified by means of chromatography on silica gel (5 % diethyl ether in petroleum ether) to afford title compound (85 % yield) as a transparent oil. ESI-MS m/z 233-235 [M+H]+; 1H NMR (300 MHz, CDCl3) delta 3.87 (s, 3H), 4.66 (s, 2H), 7.08 (d, J = 3.8Hz, 1H), 7.62 (d, J = 3.8 Hz, 1H).

82%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 12h;Reflux;	The methyl ester 13, (2.4 g, 15.5 mmol) was refluxed in CC1< in the presence of NBS (3 g, 17 mmol) and benzoyl peroxide (121 mg, 0.03 equiv) for 12 h. The reaction was cooled to 0 C and filtered. Organics was filtered, dried over Na2S04 and evaporated in vacuo. Crude material was purified on silica gel column (EtOAc: Hexanes = 1:5) to give the titled compound 14. (2.9 g, 82%). XH NMR (CHCI3, 400 MHz): delta 7.64 (d, J=3.6, 1H) , 7.10 (m, 1H) , 3.90 (s, 3H) , 3.89 (s, 3H) ; 13C NMR (CHCI3, 100 MHz): 5 162.4, 149.8, 135.5, 130.2, 124.8, 52.4, 23.4; [M+H]+ = 235.1 (APCI+) .
	With N-Bromosuccinimide; dibenzoyl peroxide; In chloroform; at 60℃; for 3h;Heating / reflux;	N-Bromosuccinimide (Aldrich; 1.70 g, 9.6 mmol) and a catalytic amount of benzoyl peroxide were added to a solution of 5-methyl-thiophene-2-carboxylic acid methyl ester (1.40 g, 9.0 mmol) in chloroform (15 mL). The rection mixture was stirred under argon at reflux (60 C.) for 3 h, then filtered through Celite and evaporated under reduced pressure to give 5-bromomethyl-thiophene-2-carboxylic acid methyl ester (2 g) as a yellow oil which was used directly in the next step without further purification

References: [1]Patent: WO2013/25424,2013,A1 .Location in patent: Page/Page column 8.
[2]Patent: WO2006/65703,2006,A1 .Location in patent: Page/Page column 128.
[3]Tetrahedron Letters,2016,vol. 57,p. 920 - 923.
[4]Patent: WO2015/100363,2015,A1 .Location in patent: Page/Page column 47.
[5]Chemical Biology and Drug Design,2018,vol. 92,p. 1241 - 1254.
[6]Journal of Medicinal Chemistry,1998,vol. 41,p. 74 - 95.
[7]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934.
[8]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1241 - 1244.
[9]Patent: US2004/266856,2004,A1 .Location in patent: Page/Page column 21.
[10]RSC Advances,2016,vol. 6,p. 70046 - 70055.

6
[ 63604-59-1 ]
[ 108499-32-7 ]
[ 170499-45-3 ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 74 - 95.

7
[ 72621-20-6 ]
[ 108499-32-7 ]
[ 335414-02-3 ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

8
[ 108499-32-7 ]
[ 105100-89-8 ]
[ 335413-91-7 ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

9
[ 19432-69-0 ]
[ 108499-32-7 ]
[ 1001200-44-7 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

10
[ 108499-32-7 ]
[ 503470-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; In acetonitrile; at 60℃; for 4h;	A mixture of compound 26.2 (41 g, 176 mmol) and sodium azide (22.9 g, 352 mmol) in acetonitrile (150 mL) was stirred at 600C for 4 hours. The reaction mixture was cooled and filtered. Removal of the solvent under reduced pressure provided compound 26.3, which was used without additional purification.

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934.
[3]Patent: WO2006/65703,2006,A1 .Location in patent: Page/Page column 128.

11
[ 530145-16-5 ]
[ 108499-32-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1H-imidazole; bromine; triphenylphosphine; In dichloromethane; at 20℃; for 0.166667h;	Bromine (0.47 mL, 9.12 mmol) was added to a solution of imidazole (617 mg, 9.06 mmol) and triphenylphosphine (2.40 g, 9.15 mmol) in CH2Cl2 (30 mL) at room temperature. A solution of methyl 5-hydroxymethyl-thiophene-2-carboxylate (prepared according to the procedures described in WO2004/037808; 1.30 g, 7.59 mmol) in CH2Cl2 (10 mL) was then added. After 10 min at room temperature, the reaction mixture was concentrated in vacuo. Purification of the crude residue by flash column chromatography on 80 g of silica gel (hexane?EtOAc, gradient) afforded 1.70 g (95%) of the title compound (B).
95%	With 1H-imidazole; bromine; triphenylphosphine; In dichloromethane; at 20℃; for 0.166667h;	Preparation 1; Methyl 5-bromomethyl-thiophene-2-carboxylate (B); Bromine (0.47 mL, 9.12 mmol) was added to a solution of imidazole (617 mg, 9.06 mmol) and triphenylphosphine (2.40 g, 9.15 mmol) in CH2Cl2 (30 mL) at room temperature. A solution of methyl 5-hydroxymethyl-thiophene-2-carboxylate (prepared according to the procedures described in WO2004/037808; 1.30 g, 7.59 mmol) in CH2Cl2 (10 mL) was then added. After 10 min at room temperature, the reaction mixture was concentrated in vacuo. Purification of the crude residue by flash column chromatography on 80 g of silica gel (hexane ?EtOAc, gradient) afforded 1.70 g (95%) of the title compound (B).
84%	With 1H-imidazole; bromine; triphenylphosphine; In dichloromethane; at 20℃; for 4h;	To a flask charged with dry dichloromethane (50 mL) was added in order triphenyl phosphine (228 mg, 0.87 mmol), imidazole (59.3 mg, 0.87 mmol) and bromine (44.6muL, 0.87 mmol). The reaction mixture was then treated with a solution of 1 (100 mg, 0.58 mmol, in <n="38"/>dichloromethane (5 niL)), dropwise and stirred at room temperature under nitrogen for 4 h. When the reaction was deemed complete the mixture was concentrated to dryness under reduced pressure and subjected to flash chromatography (20%ethyl acetate/petrol) to afford the desired 5-bromomethyl-thiophene-2-carboxylic acid methyl ester (m) as colourless crystals, (115 mg, 84%).1H NMR (300 MHz, CDCl3) delta 3.89 (3H, s, CH3), 4.67 (2H, s, CH2), 7.10 (IH, m, thienylH), 7.64 (IH, d, /=3.6Hz, thienylH).HPLCmethod2 92%/1.14 min.

References: [1]Patent: US2007/293551,2007,A1 .Location in patent: Page/Page column 23.
[2]Patent: US2009/247527,2009,A1 .Location in patent: Page/Page column 24.
[3]Patent: WO2007/124546,2007,A1 .Location in patent: Page/Page column 36-37.

12
[ 108499-32-7 ]
[ 960205-67-8 ]

Yield	Reaction Conditions	Operation in experiment
39%		Sodium hydride (60% oil dispersion, 26 mg, 0.65 mmol) was added to a solution of alcohol 2 (180 mg, 0.44 mmol) in DMF (1.1 mL) at 0 C. After 5 min, the reaction was allowed to warm to room temperature. After 30 min at room temperature, the mixture was cooled to a -40 C. and a solution of bromide B (Preparation 1, 125 mg, 0.53 mmol) in DMF (1.1 mL) was added via cannula. After 3 h at -40 C., the reaction was quenched with 1 N HCl (10 mL) and extracted with EtOAc (3×30 mL). The combined extracts were washed with H2O (2×15 mL) and brine (20 mL), then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the crude residue by flash column chromatography on 12 g of silica gel (hexane?EtOAc, gradient) afforded 97 mg (39%) of desired product 3.

References: [1]Patent: US2007/293551,2007,A1 .Location in patent: Page/Page column 22.

13
[ 1918-79-2 ]
[ 108499-32-7 ]

Yield	Reaction Conditions	Operation in experiment
		5-Bromomethyl-2-carbomethoxythiophene (III-3). This compound was prepared from 5-methylthiophene-2-carboxylic acid by the method of Gogte et al, Tetrahedron, 23, 2443-51 (1967).
		Synthesis Example 14-1: Synthesis of 2-bromomethyl-5-methoxy carbonylthiophene (Compound IV-4) 2.05 g of commercially available 5-methylthiophene carboxylic acid was dissolved in 60 ml of methanol, and then a hydrochloric acid gas was brown into the solution for 5 minutes. After 23 hours, the reaction solution was concentrated, and then a 1 mol/l sodium hydroxide aqueous solution was added thereto, followedbyextractionwithchloroform. An organic layer was washed with a saturated salt solution and was then dried with anhydrous sodium sulfate and concentrated. 500 mg of the resulting residue was dissolved in 10 ml of carbon tetrachloride, followed by the addition of 570 mg of N-bromosuccinimide and 53 mg of azobisisobutyronitrile. After the resultant solution was stirred in oil bath for 20 hours at 70C, the reaction solution was filtrated, and then the filtrate thereof was then concentrated. The resulting residue was purified by means of silica gel column chromatography (15 g, hexane/ethyl acetate = 8/1). Consequently, 516.1 mg of the above-mentioned compound was obtained as light-yellow syrup. MS(EI,Pos.):m/z=233,235[M+1]+ 1H-NMR(500MHz,CDCl3):delta=3.89(3H,s),4.68(2H,s),7.10(1H,d,J=3.7Hz),7.64(1H,d,J=3.7Hz).
	With N-Bromosuccinimide; dibenzoyl peroxide; In methanol; tetrachloromethane; methyl 5-methylthiophene-2-carboxylate;	(ii) 5-bromomethyl-2-carbomethoxythiophene A solution of 5-methyl-2-thiophene carboxylic acid (25 g, 0.176 mol) in 500 ml of methanol was saturated with gaseous hydrochloric acid at 0 C. The reaction mixture was stirred at room temperature for 18 hours and then refluxed for 48 hours. The solvent was removed in vacuo and the crude methyl 5-methyl-2-thiophene carboxylate was used without further purification. The methyl ester prepared above (11.07 g, 0.071 mol) was dissolved in 200 ml of carbon tetrachloride under argon. N-bromosuccinimide (13.25 g, 0.074 mol) and dibenzoyl peroxide were then added. The reaction mixture was refluxed for 2 hours and allowed to stand at room temperature for 18 hours. The solids were collected and the filtrate was concentrated in vacuo to give 19 g of 5-bromomethyl-2-carbomethoxythiophene.

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934.
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.
[3]Patent: US5354751,1994,A .
[4]Patent: EP1389460,2004,A1 .Location in patent: Page/Page column 38.
[5]Patent: WO2013/25424,2013,A1 .
[6]Patent: WO2015/100363,2015,A1 .
[7]Tetrahedron Letters,2016,vol. 57,p. 920 - 923.
[8]RSC Advances,2016,vol. 6,p. 70046 - 70055.
[9]Chemical Biology and Drug Design,2018,vol. 92,p. 1241 - 1254.
[10]Patent: US5447949,1995,A .

14
[ 108499-32-7 ]
[ 75985-18-1 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934.
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

15
[ 108499-32-7 ]
[ 830331-51-6 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934.

16
[ 108499-32-7 ]
[ 830331-52-7 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934.

17
[ 108499-32-7 ]
4-chloro-N-(5-{N'-[4-(3-chloro-5-trifluoromethyl-pyridin-2-ylamino)-butyryl]-hydrazinocarbonyl}-thiophen-2-ylmethyl)-benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934.

18
[ 108499-32-7 ]
[ 476362-82-0 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

19
[ 108499-32-7 ]
5-[(4-tert-butoxy-3-carboxy-benzenesulfonylamino)-methyl]-thiophene-2-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

20
[ 108499-32-7 ]
[ 476362-84-2 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

21
[ 108499-32-7 ]
[ 476362-83-1 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

22
[ 108499-32-7 ]
5-({5-[1-carboxymethyl-2-(7-methyl-benzoxazol-2-yl)-2-oxo-ethylcarbamoyl]thiophen-2-ylmethyl}sulfamoyl)-2-hydroxy-benzoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

23
[ 108499-32-7 ]
5-[(5-{1-carboxymethyl-2-[5-(2,6-dichloro-phenyl)-oxazol-2-yl]-2-oxo-ethylcarbamoyl}thiophen-2-ylmethyl)sulfamoyl]-2-hydroxy-benzoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

24
[ 108499-32-7 ]
5-({5-[1-tert-butoxycarbonylmethyl-2-hydroxy-2-(7-methoxy-benzooxazol-2-yl)-ethylcarbamoyl]-thiophen-2-ylmethyl}-sulfamoyl)-2-hydroxy-benzoic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

25
[ 108499-32-7 ]
5-({5-[1-tert-butoxycarbonylmethyl-2-(7-methoxy-benzooxazol-2-yl)-2-oxo-ethylcarbamoyl]-thiophen-2-ylmethyl}-sulfamoyl)-2-hydroxy-benzoic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

26
[ 108499-32-7 ]
[ 503470-03-9 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

27
[ 108499-32-7 ]
[ 503470-02-8 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5005 - 5022.

28
[ 108499-32-7 ]
5-(4'-dodecyloxy-biphenyl-4-yloxymethyl)-thiophene-2-carbonyl chloride [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

29
[ 108499-32-7 ]
5-(4'-dodecyloxy-biphenyl-4-yloxymethyl)-thiophene-2-carboxylic acid sec-butyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

30
[ 108499-32-7 ]
5-(4'-dodecyloxy-biphenyl-4-yloxymethyl)-thiophene-2-carboxylic acid butyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

31
[ 108499-32-7 ]
5-(4'-dodecyloxy-biphenyl-4-yloxymethyl)-thiophene-2-carboxylic acid 1-methyl-butyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

32
[ 108499-32-7 ]
5-(4'-dodecyloxy-biphenyl-4-yloxymethyl)-thiophene-2-carboxylic acid 1-methyl-pentyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

33
[ 108499-32-7 ]
5-(4'-dodecyloxy-biphenyl-4-yloxymethyl)-thiophene-2-carboxylic acid 1-methyl-heptyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

34
[ 108499-32-7 ]
(R)-(+)-2-heptyl 5-(4'-dodecyloxybiphenyl-4-yloxymethyl)thiophene-2-carboxylate [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

35
[ 108499-32-7 ]
5-(4'-dodecyloxy-biphenyl-4-yloxymethyl)-thiophene-2-carboxylic acid octyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

36
[ 108499-32-7 ]
potassium; 5-(4'-dodecyloxy-biphenyl-4-yloxymethyl)-thiophene-2-carboxylate [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 741 - 748.

37
[ 108499-32-7 ]
[ 170499-46-4 ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 74 - 95.

38
[ 108499-32-7 ]
5-(2-Methyl-imidazo[4,5-c]pyridin-1-ylmethyl)-thiophene-2-carbonyl chloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 74 - 95.

39
[ 108499-32-7 ]
[ 133446-65-8 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

40
[ 108499-32-7 ]
[ 133446-67-0 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

41
[ 108499-32-7 ]
[ 133446-70-5 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

42
[ 108499-32-7 ]
[ 133446-48-7 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

43
[ 108499-32-7 ]
[ 133446-66-9 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2209 - 2218.

44
[ 108499-32-7 ]
[ 31127-39-6 ]
[ 773059-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; water; for 0.666667h;	To a solution of 500mg (2. 13MMOL) 5-BROMOMETHYL-THIOPHENE-2-CARBOXYLIC acid methyl ester and 381mg (2.13mmol) 2,3-dihydro-benzo [1, 4] dioxine-6- carbaldehyde oxime in 2ML dichloromethane were added 2. 0ml 2.2M aqueous sodium hydroxide solution and 902mg (2.55mmol) tertrabutylammonium hydrogen sulfate while vigorously stirring. After 10 minutes another 2. 0ML 2.2M aqueous sodium hydroxide solution and 902mg (2. 55MMOL) tertrabutylammonium hydrogen sulfate were added. This procedure was repeated one more time. After 20 minutes 8ml saturated aqueous bicarbonate solution was added. The aqueous phase was extracted three times with ethyl acetate and the combined organic phases were washed with brine and dried over NA2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (hexane/ethyl acetate 4: 1, then 3: 1) to yield 214mg (0. 64MMOL) 5- (2, 3-Dihydro-benzo [1, 4] dioxin-6- ylmethyleneaminooxymethyl) -thiophene-2-carboxylic acid methyl ester; exact MW [M+H] calc'd: 334.07 ; MW found [M+H]: 334.2

References: [1]Patent: WO2004/87693,2004,A1 .Location in patent: Page 17.

Yield	Reaction Conditions	Operation in experiment
		Methyl 5-bromomethylthiophene-2-carboxylate may be prepared according to Curtin M. L., Davidsen S. K., Heyman H. R., Garland R. B., Sheppard G. S., J. Med. Chem., 1998, 41 (1), 74-95.
		This compound is shown in Table 1 as compound 3. Preparation of thiophene analogues of 10deazaaminopterins is illustrated in Reaction Scheme 3. Starting compounds III-1 and III-2, namely 5-methylthiophene-2-carboxylic acid and methyl 5-methylthiophene-2-carboxylate, are commercially available from Sigma, St Louis, Mo. 5-Bromomethyl-2-carbomethoxythiophene (III-3) is prepared from 5-methylthiophene-2-carboxylic acid by the method described in Tetrahedron, 23:2443-51 (1967). A mixture of III-3, sodium cyanide, benzyltrimethylammonium chloride, dichloromethane, and water is stirred rapidly for about 16 hours.
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃;	General procedure: Preparation Example 62 To a mixture of 5.27 g of benzyl 5-methylthiophene-2-carboxylate and 100 mL of carbon tetrachloride were added 4.18 g of N-bromosuccinimide (NBS) and 142 mg of azobisisobutyronitrile (AIBN), followed by stirring overnight at 80C. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3), thereby obtaining 4.44 g of benzyl 5-(bromomethyl)thiophene-2-carboxylate.

46
[ 108499-32-7 ]
[ 261925-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; ethanol; sodium methansulfinate;	Methyl 5-(methylsulfonylmethyl)thiophene-2-carboxylate may be prepared in the following manner: 6.94 g of sodium methanesulfinate are added, at room temperature, to a solution of 16 g of <strong>[108499-32-7]methyl 5-bromomethylthiophene-2-carboxylate</strong> in 150 cm3 of tetrahydrofuran. The suspension is stirred for 2 hours 30 min under reflux, and then after addition of 50 cm3 of ethanol is again stirred for 3 hours under reflux. The mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue obtained is supplemented with 150 cm3 of distilled water and is then extracted with twice 300 cm3 of ethyl acetate. The organic phase is successively washed with 100 cm3 of distilled water and twice 50 cm3 of saturated aqueous sodium chloride solution and then dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). 14 g of methyl 5-(methylsulfonylmethyl)thiophene-2-carboxylate are thus obtained in the form of a yellow solid melting around 133 C. [1H NMR spectrum (400 MHz, (CD3)2SO-d6, at a temperature of 373 K, delta in ppm): 3.05 (s, 3H), 4.22 (mt, 2H), 4.40 (mt, 2H), 4.98 (broad s, 1H), 7.30 (d, J=3.5 Hz, 1H), 7.39 (d, J=8 Hz, 4H), 7.50 (d, J=8 Hz, 4H), 7.66 (d, J=3.5 Hz, 1H)].

References: [1]Patent: US2002/35102,2002,A1 .

47
[ 4177-91-7 ]
[ 108499-32-7 ]
5-(8-chloro-10,11-dihydrodibenzo[b,f][1,41-thiazepin-10-ylmethyl)thiophene-2-carboxylic acid [ No CAS ]
methyl 5-(8-chloro-10,11-dihydrodibenzo[b,f][1,4]thiazepin-10-ylmethyl)thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In acetic acid; N,N-dimethyl-formamide; mineral oil;	EXAMPLE 4 A solution of 8-chloro-10,11-dihydrodibenzo[b,f][1,4]-thiazepine (Coll. Czech. Chem. Comm., 1959, 24, 207; 2 g) in DMF (20 ml) was added dropwise to a stirred suspension of sodium hydride (60% w/v dispersion in mineral oil, 0.38 g) in DMF (5 ml) which had been cooled to 0 C. The mixture was stirred at 0 C. for 30 minutes. A solution of <strong>[108499-32-7]methyl 5-bromomethylthiophene-2-carboxylate</strong> (1.89 g) in DMF (5 ml) was added dropwise. The mixture was allowed to warm to ambient temperature and was stirred for 18 hours. The mixture was poured onto ice and acidified by the addition of glacial acetic acid. The mixture was extracted with diethyl ether (3*50 ml). The combined extracts were washed with water and with brine, dried (MGSO4) and evaporated. The residue was purified by column chromatography using a 3:2 v/v mixture of hexane and methylene chloride as eluent. There was thus obtained methyl 5-(8-chloro-10,11 -dihydrodibenzo[b,f][1,4]thiazepin-10-ylmethyl)thiophene-2-carboxylate in 13% yield. The product so obtained was hydrolyzed using an analogous procedure to that described in the second paragraph of Example 1. There was thus obtained 5-(8-chloro-10,11-dihydrodibenzo[b,f][1,41-thiazepin-10-ylmethyl)thiophene-2-carboxylic acid in 61% yield, m.p. 216-217 C.

References: [1]Patent: US5317101,1994,A .

48
[ 56-93-9 ]
[ 108499-32-7 ]
methyl 5-(cyanomethyl)thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; dichloromethane; water; ethyl acetate;	5-Cyanomethyl-2-carbomethoxythiophene (III-4) A mixture of III-3 (18.0 g, 76.6 mmol), sodium cyanide (15.0 g, 0.31 mmol), benzyltrimethylammonium chloride (1.75 g, 9.4 mmol), dichloromethane (75 mL), and water (75 mL) was stirred rapidly for 16 hours. The mixture was then separated. The organic layer was treated first with water (75 mL), then with sodium cyanide (15.0 g, 0.31 mmol), and last with benzyltrimethylamonium chloride (1.5 g, 8.0 mmol). This mixture was again rapidly stirred for 24 hours. The organic layer was removed, dried over magnesium sulfate, and concentrated. The residue was chromatographed on 250 g of flash silica gel using 20% ethyl acetate in hexane as an eluent, to give the product (III-4) as a yellow crystalline solid, 4.53 g (33%). Analysis gave the following results. NMR (CDCl3) d 7.66 (d, 1H, C3 -H); 7.03 (d, 1H, C4 -H); 3.83 (d, 5H, CH3 +CH2); mass spectrum m/e 196 (M +H); TLC (10% ethyl acetate in hexanes on silica gel plates); Rf -0.3.

References: [1]Patent: US5354751,1994,A .

Yield	Reaction Conditions	Operation in experiment
28%		Preparation 20 Methyl 5-(bromomethyl)-2-thiophene carboxylate The title compound of Preparation 19 (1.9 g, 12.2 mmol), N-bromosuccinimide (NBS, 2.2 g, 12.4 mmol), and benzoyl peroxide (20 mg, 0.08 mmol) were combined with 125 ml CCl4 under an inert atmosphere at room temperature. The reaction mixture was heated to 87 for 4 hrs. An additional 540 mg of NBS (3.0 mmol) and 75 mg of benzoyl peroxide (0.3 mmol) were then added and the reaction mixture was stirred for another hour at 87. The reaction mixture was filtered while hot and the filtrate was stripped to provide the title compound of this Preparation (811 mg, 28% yield) as a brown oil. 1 H NMR (CDCl3): delta 7.63 (1H, d, J=4), 7.09 (1H, d, J=4), 4.68 (2H, s), 3.89 (3H, s).

50
[ 19432-69-0 ]
hexanes-ethyl acetate [ No CAS ]
2,2'-aza-bis-isobutyronitrile [ No CAS ]
[ 108499-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In tetrachloromethane;	Preparation of 5-Bromomethyl-thiophene-2-carboxylic acid methyl ester (T-1). 5-Methyl-thiophene-2-carboxylic acid methyl ester (20.0 g, 0.13 mol) was dissolved in a suspension of N-bromosuccinimide (45.4 g, 0.26 mol) and 2,2'-aza-bis-isobutyronitrile (0.1 g, 0.61 mmol) in 1 L of carbon tetrachloride. The suspension was refluxed for 48 hours then cooled and the precipitate was filtered off. The filtrate was concentrated and the residue was purified on silica gel (100% hexanes then 9:1 Hexanes-Ethyl acetate) to provide a 26 g fraction containing mainly the di-brominated compound 5-dibromomethyl-thiophene-2-carboxylic acid methyl ester as a yellow oil and a more polar fraction (7.5 g) containing mainly compound T-1 (25% yield) as a yellow oil (70% purity).

References: [1]Patent: US6274620,2001,B1 .

51
[ 108499-32-7 ]
[ 148564-13-0 ]
C₄₉H₄₄N₆O₃S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1241 - 1244.

52
[ 1047668-30-3 ]
[ 108499-32-7 ]
[ 1047668-31-4 ]

Yield	Reaction Conditions	Operation in experiment
38%		[203] Step 3. Alkylation of 3 with B to give 4; [204] Sodium hydride (9 mg of a 60% dispersion in oil, 0.23 mmol) was added to a solution of 3 (40 mg,0.15 mmol) in DMF (0.36 mL) at 0 0C. The mixture was allowed to warm to room temperature. After 30 min <n="29"/>at room temperature, a solution of B (see US Provisional Patent Application No. 60/804,680, filed June 14, 2006, incorporated by reference herein, 29 mg, 0.12 mmol) in DMF (0.36 mL) was added. After 10 min the reaction was partitioned between water (10 mL) and CH2CI2 (20 mL). The phases were separated and the aqueous phase was extracted with CH2CI2 (2x10 mL). The combined organic phase was dried (MgSO-t), filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography on 4 g silica (hexane -> EtOAc, gradient) to afford 20 mg (38%) of 4.

References: [1]Patent: WO2008/100809,2008,A1 .Location in patent: Page/Page column 27-28.

53
[ 1073242-22-4 ]
[ 108499-32-7 ]
[ 1073242-23-5 ]

Yield	Reaction Conditions	Operation in experiment
45%		Step 2. Alkylation of 56 to Give 57; Sodium hydride (60% dispersion in oil, 26 mg, 0.65 mmol) was added to a solution of alcohol 56 (120 mg, 0.44 mmol) at 0 C. and the mixture was allowed to warm to room temperature. After 20 minutes, the mixture was cooled to -40 C. and a solution of <strong>[108499-32-7]methyl 5-(bromomethyl)thiophene-2-carboxylate</strong> (125 mg, 0.53 mmol) in DMF (1.1 mL) was added via cannula. After 1 hours at -40 C. the reaction was quenched with 0.5 N HCl (15 mL) and extracted with EtOAc (3×30 mL). The combined extracts were washed with water (2×20 mL) and brine (20 mL) then dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified on 12 g silica (hexanes?EtOAc, gradient) to afford 84 mg (45%) of 57.

References: [1]Patent: US2008/269498,2008,A1 .Location in patent: Page/Page column 13-14.

54
[ 1084897-46-0 ]
[ 108499-32-7 ]
[ 1084897-50-6 ]

Yield	Reaction Conditions	Operation in experiment
13%		Sodium hydride (60% oil dispersion, 40 mg, 1.0 mmol) was added to a solution of alcohol 10 (200 mg, 0.51 mmol) in DMSO (1.25 mL) at room temperature. After 30 <n="18"/>min at room temperature, a solution of bromide B (see Allergan docket No.17833, 130 mg, 0.55 mmol) in DMSO (1.25 mL) was added via cannula. After 15 min at room temperature, the mixture was heated at 40 0C. After 16 h at 40 0C, the mixture was allowed to cooled to room temperature, quenched with saturated aqueous NH4Cl (5 mL) and 0.5 N HCl (15 mL) and extracted with EtOAc (3x40 mL). The combined extracts were washed with H2O (2x20 mL) and brine (20 mL), then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the crude residue by flash column chromatography on 4 g of silica gel (hexane - > EtOAc, gradient) afforded 36 mg (13%) of desired product 11.

References: [1]Patent: WO2008/144623,2008,A1 .Location in patent: Page/Page column 16-17.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 108499-32-7

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CAS No.: 108499-32-7

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[ 108499-32-7 ] Synthesis Path-Downstream 1~54

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