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tert-butyl [4-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-3-[(3R)-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}benzyl]-carbamate[ No CAS ]
5-[4-(aminomethyl)-2-[(3R)-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-carbonyl}phenyl]-N-[4-(benzyloxy)phenyl]-N,1,2-trimethyl-1H-pyrrole-3-carboxamide hydrochloride[ No CAS ]
tert-butyl {2-[3-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-4-[(3R)-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}phenyl]ethyl}-carbamate[ No CAS ]
5-[5-(2-aminoethyl)-2-[(3R)-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-carbonyl}phenyl]-N-[4-(benzyloxy)phenyl]-N,1,2-trimethyl-1H-pyrrole-3-carboxamide hydrochloride[ No CAS ]
phenyl [2-(3-{4-[(4-hydroxyphenyl)(methyl)carbamoyl]-1,5-dimethyl-1H-pyrrol-2-yl}-4-[(3R)-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}phenyl)ethyl]-carbamate[ No CAS ]
N-[4-(benzyloxy)phenyl]-N,1,2-trimethyl-1H-pyrrole-3-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Step A: N-(4-Benzyloxyphenyl)-N,1,2-trimethyl-pyrrole-3-carboxamide To a suspension of <strong>[89776-57-8]1,2-dimethylpyrrole-3-carboxylic acid</strong> (2.085 g; 15 mmol) in 1,2-dichloroethane (40 mL) there is added 1-chloro-N,N,2-trimethyl-prop-1-en-1-amine (2.37 mL; 17.9 mmol), and the solution formed is stirred for 1 hour. To the resulting solution there is added, dropwise, an ice-cold solution of 4-benzyloxy-N-methyl-aniline (3.73 g; 15 mmol) and N-ethyl-N-isopropyl-propan-2-amine (7.75 mL; 45 mmol) in 1,2-dichloroethane (40 mL). The reaction mixture is stirred at ambient temperature for 1 hour; it is then diluted with dichloromethane (250 mL) and washed with water (2*30 mL), dried over Na2SO4 and evaporated. The crude product is triturated with diethyl ether and the solid formed is filtered off to yield the title compound. IR: nu: >C=O: 1616 cm-1; amide: 1508 cm-1; C-O-C: 1230, 1172, 1009 cm-1
Step C: N-[4-(Benzyloxyfrl,enylJ-N,1,2-trirnethyl-1H-pyrrote-3-carboxan,jdeThe acid obtained from Step B (1 g, 7.19 mmol) is dissolved in dichloromethane (20 ml) and to this is added l-chloro-N,N,2-trimethyl-l-propenylamine (1.15 g, 8.62 mrnol) and stirred at ambient temperature for 2 hours, The mixture is concentrated to an oil which is re-dissolved in toluene (50 mL). A solution of 4-(benzyloxy)-N-methylaniline (1.84 g, 8.62 mmol) in toluene (10 ml) is added and the resultant mixture is stirred at reflux for 2 hours.The reaction is allowed to cool to ambient temperature and lefi to stand for cci 16 h. The reaction is partitioned between ethyl acetate and water, separated, and the organics are washed with water, dried over magnesium sulphate, filtered and concentrated. The crude product is purified on CombiFlash (80 g silica, Hex to 60% EtOAe) to obtain the desired product as a solid.LC/MS (C21H22N202) 335 [M+H] RT 1.33 (Method B)
With water; lithium hydroxide; In 1,4-dioxane; at 100.0℃; for 16h;
Step B: 1,2-Dimethyl-JH-pyrrole-3-carboxylic acid To a solution of the product from Step A (5.3 g, 31.7 mmol) in 1 ,4-dioxane (60 mL) is added lM LiOH (2.66 g, 63.4 minol) in water (60 ml) and the reaction stirred at 100 C for cci 16 h. The reaction is allowed to cool to ambient temperature, diluted with water and acidified with 2M Rd. The resulting precipitate is collected by vacuum filtration to affordthe desired product. The filtrate is extracted with ethyl acetate and the organic extracts dried over magnesium sulphate, filtered and concentrated to obtain an additional crop of desired product.LC/1VLS (C7H9N02) no ionisation; RT 0.71 (Method B)
tert-butyl 6-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carboxylate[ No CAS ]
N-[4-(benzyloxy)phenyl]-N,1,2-trimethyl-5-{7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinolin-6-yl}-1H-pyrrole-3-carboxamide bistrifluoroacetic acid salt[ No CAS ]
tert-butyl 5-[4-[(4-benzyloxyphenyl)-1-methyl-carbamoyl]-1,5-dimethyl-pyrrol-2-yl]-6-[(3S)-3-(morpholinomethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]isoindoline-2-carboxylate[ No CAS ]
N-(4-benzyloxyphenyl)-N,1,2-trimethyl-5-[6-[(3S)-3-(morpholinomethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]isoindolin-5-yl]pyrrole-3-carboxamide hydrochloride[ No CAS ]
tert-butyl 5-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-6-[(3R)-3-methyl-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-2,3-dihydro-1H-isoindole-2-carboxylate[ No CAS ]
N-[4-(benzyloxy)phenyl]-N,1,2-trimethyl-5-{6-[(3R)-3-methyl-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-2,3-dihydro-1H-isoindol-5-yl}-1H-pyrrole-3-carboxamide[ No CAS ]
N-[4-(benzyloxy)phenyl]-N,1,2-trimethyl-5-{6-[(3R)-3-methyl-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-2-(2-phenylacetyl)-2,3-dihydro-1H-isoindol-5-yl}-1H-pyrrole-3-carboxamide[ No CAS ]
6-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl chloride[ No CAS ]
3,4-dichlorophenyl 6-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carboxylate[ No CAS ]
3-[(benzyloxy)carbonyl]phenyl 6-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carboxylate[ No CAS ]
4-bromophenyl 6-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carboxylate[ No CAS ]
4-ethynylphenyl 6-{4-[(4-hydroxyphenyl)(methyl)carbamoyl]-1,5-dimethyl-1H-pyrrol-2-yl}-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carboxylate[ No CAS ]
3,4-dichlorophenyl 6-{4-[(4-hydroxyphenyl)(methyl)carbamoyl]-1,5-dimethyl-1H-pyrrol-2-yl}-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carboxylate[ No CAS ]
3-(6-{4-[(4-hydroxyphenyl)(methyl)carbamoyl]-1,5-dimethyl-1H-pyrrol-2-yl}-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyloxy)benzoic acid[ No CAS ]
4-bromophenyl 6-{4-[(4-hydroxyphenyl)(methyl)carbamoyl]-1,5-dimethyl-1H-pyrrol-2-yl}-7-[(3S)-3-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-2-carboxylate[ No CAS ]
N-(4-hydroxyphenyl)-N,1,2-trimethyl-5-{6-[(3R)-3-methyl-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]-2-(2-phenylacetyl)-2,3-dihydro-1H-isoindol-5-yl}-1H-pyrrole-3-carboxamide[ No CAS ]
2-tert-butyl 7-methyl 6-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-1,2,3,4-tetrahydroisoquinoline-2,7-dicarboxylate[ No CAS ]
2-tert-butyl 7-lithio 6-(4-[4-(benzyloxy)phenyl](methyl)carbamoyl}-1,5-dimethyl-1H-pyrrol-2-yl)-1,2,3,4-tetrahydroisoquinoline-2,7-dicarboxylate[ No CAS ]
N-(4-fluoro-3-methylphenyl)-1,2-dimethyl-1H-pyrrole-3-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
39%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 50.0℃; for 112h;
To a solution of <strong>[89776-57-8]1,2-dimethyl-1H-pyrrole-3-carboxylic acid</strong> (1.0 g, 7.19 mmol), 3-methyl-4-fluoroaniline (989 mg, 7.91 mmol) and HATU (3.28 g, 8.63 mmol) in DMF (20 mL) was added DIPEA (3.76 mL, 21.57 mmol). After 96 h, the reaction mixture was warmed to 50 C. After an additional 16 h, the reaction mixture was cooled to ambient temperature, diluted with EtOAc and washed successively with 1N HCl, NaHCO3 (sat), and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified via flash chromatography on silica gel (EtOAc/hexanes 5-60%) to afford the title compound (690 mg, 39%) as an off-white solid ESI-MS, m/z 247.2 (MH)+
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