* 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.
9,10-dihydro-phenanthrene-2,7-dicarboxylic acid bis-({4-[5-(3-dimethylamino-propylcarbamoyl)-1-methyl-1<i>H</i>-pyrrol-3-ylcarbamoyl]-5-methyl-thiophen-2-yl}-amide)[ No CAS ]
2-Methyl-3-thiophenecarboxyalic acid (5.69 g) synthesised in the same manner as Reference Example 127 was dissolved in N,N-dimethylformamide (50 ml), and iodoethane (3.2 ml) and potassium carbonate (5.52 g) were added. The reaction mixture was stirred at room temperature for 15 hours, and poured into water, and then extracted with diethyl ether. The extract was washed with 5% aqueous potassium hydrogen sulfate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a crude product of 2-methyl-3-thiophenecarboxylic acid ethyl ester.
10
sodium thiosulfate[ No CAS ]
[ 19432-66-7 ]
5-chloro-2-methyl-3-thiophenecarboxylic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sulfuryl dichloride; In acetonitrile;
This crude product of <strong>[19432-66-7]2-methyl-3-thiophenecarboxylic acid ethyl ester</strong> was dissolved in acetonitrile (50 ml), and sulfuryl chloride (3.0 ml) in acetonitrile (20 ml) was added dropwise. The mixture was stirred for 1 hour under cooling over a water bath, and then 10% aqueous sodium thiosulfate (100 ml) was added. The mixture was stirred at room temperature for 2 hours, and extracted with diethyl ether. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product of 5-chloro-<strong>[19432-66-7]2-methyl-3-thiophenecarboxylic acid ethyl ester</strong>.
With potassium carbonate; In N,N-dimethyl-formamide;
Reference Example 144 4-Chloro-5-methyl-2-thiophenecarboxylic Acid 5-Methyl-2-thiophenecarboxylic acid (2.84 g) was dissolved in N,N-dimethylformamide (30 ml), and iodoethane (1.68 ml) and potassium carbonate (2.76 g) were added. The mixture was stirred at room temperature for 15 hours, poured into water and extracted with diethyl ether. The extract was washed with 5% aqueous potassium hydrogen sulfate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-methyl-3-thiophenecarboxylic acid ethyl ester (1.84 g).
(R)-methyl 3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate[ No CAS ]
(R)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid[ No CAS ]
(S)-benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-((2-((4-ethylpiperidin-1-yl)methyl)-1H-imidazol-1-yl)methyl)-5-methylthiophen-2-yl)-2,2-dimethylpropanoate[ No CAS ]
(S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-((2-((4-ethylpiperidin-1-yl)methyl)-1H-imidazol-1-yl)methyl)-5-methylthiophen-2-yl)-2,2-dimethylpropanoic acid[ No CAS ]
(S)-benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-((4,6,6-trimethyl-3-oxo-1,4-diazepan-1-yl)methyl)thiophen-2-yl)propanoate[ No CAS ]
(S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-((4,6,6-trimethyl-3-oxo-1,4-diazepan-1-yl)methyl)thiophen-2-yl)propanoic acid[ No CAS ]
(S)-benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((R)-4-methyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanoate[ No CAS ]
(S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((R)-4-methyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanoic acid[ No CAS ]
(S)-benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((R)-4-methyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanoate[ No CAS ]
(S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((R)-4-methyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanoic acid[ No CAS ]
(S)-benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanoate[ No CAS ]
(S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanoic acid[ No CAS ]
(S)-benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanoate[ No CAS ]
(S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanoic acid[ No CAS ]
ethyl 5-bromo-2-methylthiophene-3-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%
With N-Bromosuccinimide; acetic acid; In N,N-dimethyl-formamide; at 20℃; for 20h;
N-bromosuccinimide (6.53 g, 36.7 mmol) was slowly added to a solution of ethyl2-methylthiophene-3-carboxylate (5.07 g, 32.5 mmol) in DMF (60 mL) and acetic acid (40 mL) at roomtemperature over 10 mm. After addition, the reaction was stirred at room temperature for 12 h. The reaction was quenched with sat. aq. NaHCO3 and extracted with EtOAc (100 mL). The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by a silica gel chromatography using 0-3% EtOAc in hexane to afford the title compound (7.17 g, 20.6 mmol, 94% yield) as a white solid.LC-MS [M+Hj = 249.
73%
With N-Bromosuccinimide; acetic acid; In N,N-dimethyl-formamide; at 20℃; for 20h;Cooling with ice;
To a solution of <strong>[19432-66-7]ethyl 2-methylthiophene-3-carboxylate</strong> (10.00 g, 58.7 mmol) in N,Ndimethylformamide (DMF) (60 mL) was added acetic acid (40 mL). The reaction warmed up after adding acetic acid to DMF solution so it was cooled in ice bath. NBS (10.46 g,58.7 mmol) was then added and the reaction was stirred at ambient temperature for 20h. The reaction was diluted with water and extracted with EtOAc (3X). The combined organics were washed with water, saturated NaHSO3, brine, dried with MgSO4 and concentrated. The residue was redissolved in EtOAc and washed with water (4X), brine, dried with MgSO4 and concentrated. The solvent was concentrated and the residue waspurified by flash chromatography eluting with 0-5% EtOAc I hexane to provide the title compound. (12.32 g, 73% yield). LCIMS m/z = 248/250 (M+H)+, 1 .21 mm (ret. time).
methyl 3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)propanoate[ No CAS ]
3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)propanoic acid[ No CAS ]
(S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)propanoic acid[ No CAS ]
benzyl (S)-3-(4-(((S)-3-(1H-pyrazol-1-yl)piperidin-1-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate[ No CAS ]
(S)-3-(4-(((S)-3-(1H-pyrazol-1-yl)piperidin-1-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid[ No CAS ]
(S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)propanamide[ No CAS ]
(R)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)propanoic acid[ No CAS ]
(R)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[4,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)propanoic acid[ No CAS ]
(S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-N-(pyridin-3-yl)propanamide[ No CAS ]
(S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)-N-(pyridin-3-yl)propanamide[ No CAS ]
benzyl (S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiophen-2-yl)-2,2-dimethylpropanoate[ No CAS ]
benzyl (R)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiophen-2-yl)-2,2-dimethylpropanoate[ No CAS ]
benzyl (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-8-(trifluoromethyl)-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate[ No CAS ]
(S)-3-(4-(((S)-4-ethyl-1,1-dioxido-8-(trifluoromethyl)-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid[ No CAS ]
benzyl (R)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoate[ No CAS ]
(R)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoic acid[ No CAS ]
benzyl (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoate[ No CAS ]
(S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoic acid[ No CAS ]
benzyl (S)-3-(4-(((R)-2-ethyl-2,3-dihydropyrido[2,3-f][1,4]oxazepin-4(5H)-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate[ No CAS ]
(S)-3-(4-(((R)-2-ethyl-2,3-dihydropyrido[2,3-f][1,4]oxazepin-4(5H)-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid[ No CAS ]
benzyl (R)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)pentanoate[ No CAS ]
(R)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)pentanoic acid[ No CAS ]
benzyl (S)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)pentanoate[ No CAS ]
(S)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)thiophen-2-yl)pentanoic acid[ No CAS ]
benzyl (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoate[ No CAS ]
(S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoic acid[ No CAS ]
benzyl (R)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoate[ No CAS ]
(R)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-2,2-dimethylpentanoic acid[ No CAS ]
(S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid[ No CAS ]
methyl 3-(4-(((tert-butyldimethylsilyl)oxy)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate[ No CAS ]
(S)-benzyl 3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate[ No CAS ]
(S)-3-(4-((4,4-dimethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid[ No CAS ]
(S)-benzyl 3-(4-((4,4-dimethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate[ No CAS ]
(S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[4,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiophen-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid[ No CAS ]
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