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[ CAS No. 1797406-69-9 ] {[proInfo.proName]}

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Chemical Structure| 1797406-69-9
Chemical Structure| 1797406-69-9
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Product Details of [ 1797406-69-9 ]

CAS No. :1797406-69-9 MDL No. :N/A
Formula : C49H60ClN9O8S2 Boiling Point : -
Linear Structure Formula :- InChI Key :PTAMRJLIOCHJMQ-PYNGZGNASA-N
M.W : 1002.64 Pubchem ID :122201421
Synonyms :

Safety of [ 1797406-69-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1797406-69-9 ]

* 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 [ 1797406-69-9 ]

[ 1797406-69-9 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 1448191-54-5 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: dichloromethane / 0.5 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 5: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 6: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 2
  • [ 1448189-98-7 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloromethane / 0.5 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 3: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 3
  • [ 1631137-40-0 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2: dichloromethane / 0.5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 4: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 5: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 4
  • [ 1631137-51-3 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 5
  • [ 112-27-6 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: triethylamine / tetrahydrofuran / 0 - 25 °C 2.1: sodium azide / ethanol / 18 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C 3.2: 18 h / 0 - 25 °C 4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 5.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 6.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 6
  • [ 77544-68-4 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium azide / ethanol / 18 h / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C 2.2: 18 h / 0 - 25 °C 3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 4.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 7
  • [ 86520-52-7 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C 1.2: 18 h / 0 - 25 °C 2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 8
  • [ 172531-37-2 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 9
  • [ 1797406-80-4 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 10
  • [ 1448189-30-7 ]
  • (2S,4R)-1-[(2S)-2-(2-{2-[2-(2-{2-[(9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaen-9-yl]acetamido}ethoxy)ethoxy]ethoxy}acetamido)-3,3-dimethylbutanoyl]-4-hydroxy-N-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}pyrrolidine-2-carboxamide [ No CAS ]
  • 11
  • [ 202592-23-2 ]
  • [ 2010159-56-3 ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
9.51 mg 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 dichloromethane at 25℃; for 18h; General procedure for making PROTACs of structure A-L-B, from de-protected intermediates General procedure: The starting azide, of structure Az-L-A, such as for example intermediate compound (13) (40 umol) was dissolved in methanol (5 ml). A catalytic amount of palladium on charcoal (10 wt%) was added and the reaction mixture was then stirred under an atmosphere of hydrogen gas for about 3 h at 25°C. The reaction mixture was then filtered through a plug of celite and the resulting solution evaporated to dryness to obtain the desired intermediate amine, corresponding to the starting azide which was then linked to the desired B-group without further purification. The intermediate amine, in this general example, the amine equivalent of intermediate compound (13) (35 umol, 1.4 eq.) and the desired B-group, in this general example suitable B-groups include the: free acid of JQ1 (11.4 mg, 25 μιηο, 1 eq.), or I-BET726 (10.9 mg, 25 umol, 1 eq.), or free acid of I-BET762 (9.92 mg, 25 umol, 1 eq.), were then dissolved in DCM (2 ml). HATU (14.3 mg, 37.5 umol, 1.5 eq.) was then added and the pH of the resultant mixture was adjusted to >9 by adding DIPEA (17.5 μ, 100 umol, 4 eq.). After stirring the reaction mixture at 25°C for 18 h the solvent was removed in vacuum. Purification of the crude product was achieved by preparative HPLC as described in the general information in order to furnish the desired PROTAC. For the avoidance of doubt, such intermediate amines are prepared from the corresponding de-protected azides by any suitable methods, and in particular, via reduction over palladium, with the resultant amines being utilized directly without further purification. Any PROTAC compound of structure A-L-B can be prepared in accordance with the general procedure outlined starting from intermediate compounds (13), by use of the appropriate starting Az-L-A compound and the desired B-group, as outlined in Scheme 2. PROTAC compounds MZl, MZ2, MZ3, MZP-11, MZP-15, MZP-25, MZP-54, MZP-55, MZP-60 and MZP-61 as detailed herein after were prepared in accordance with the above general methodology from the appropriate starting azide and B-group.
  • 12
  • [ 1268524-70-4 ]
  • (2S,4R)-1-[(2S)-2-(2-{2-[2-(2-{2-[(9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaen-9-yl]acetamido}ethoxy)ethoxy]ethoxy}acetamido)-3,3-dimethylbutanoyl]-4-hydroxy-N-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}pyrrolidine-2-carboxamide [ No CAS ]
  • 13
  • [ CAS Unavailable ]
  • [ 1797406-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: palladium diacetate; potassium acetate / N,N-dimethyl acetamide / 150 °C 2.1: sodium tetrahydroborate; cobalt(II) chloride / methanol / 1.5 h / 0 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / 20 °C 3.2: 0.5 h / 20 °C 4.1: dichloromethane / 0.5 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 6.1: dichloromethane / 0.5 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 4 h / 25 °C / pH > 9 8.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 25 °C 9.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C / pH > 9
  • 14
  • [ 122957-57-7 ]
  • (2S,4R)-1-[(2S)-2-(2-{2-[2-(2-{2-[(9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaen-9-yl]acetamido}ethoxy)ethoxy]ethoxy}acetamido)-3,3-dimethylbutanoyl]-4-hydroxy-N-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}pyrrolidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 0.333333h; 42 Preparation of (25, 4 ?)-l-[(25)-2-{2-[3-(2-{2-[(95)-7-(4-chlorophenyl)-4,5, 13- trimethyl-3-thia-l,8,l l,12-tetraazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10, 12-pentaen-9- yl]acetamido}ethoxy)propoxy]acetamido}-3,3-dimethylbutanoyl]-4-hydroxy-N-[(i5)-l-[4-(4- methyl-l,3-thiazol-5-yl)phenyl]ethyl]pyrrolidine-2-carboxamide (Example 77). General procedure: To a stirred solution of (5)-2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2- f][l,2,4]triazolo[4,3-a][l,4]diazepin-6-yl) acetic acid (900 mg, 2.32 mmol), ieri-butyl 2-(3-(2- aminoethoxy)propoxy) acetate (650 mg, 2.79 mmol), and DIPEA (1.5 g, 11.61 mmol) in anhydrous N,N-dimethylformamide (6 mL) was added HATU (2.65 mg, 6.97 mmol) at 0°C, the resulting mixture was stirred at rt for 20 min. LC-MS showed the reaction was completed. The mixture was partitioned between ethyl acetate (100 mL) and water (40 mL). The aqueous layer was extracted with ethyl acetate (50 mL x 2). The combined organic layers were collected, washed with brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel flash column chromatography (eluted with 2-10% MeOH in DCM) to afford (S)-tert-buty 2-(3-(2-(2-(4-(4- chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][l,2,4]triazolo[4,3-a][l,4]diazepin-6- yl)acetamido)ethoxy)propoxy)acetate (800 mg, yield 58%) as white solid. This solid (800 mg, 1.30 mmol) in formic acid (5 mL) was stirred at 60 °C for 1 h. TLC showed the reaction was completed. The volatiles were evaporated under reduced pressure to afford (5)-2-(3-(2-(2-(4- (4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][l,2,4]triazolo[4,3-a][l,4]diazepin-6- yl)acetamido)ethoxy)propoxy)acetic acid as a crude yellow oil without further purification. The oily material (700 mg, Crude) was mixed with (25,4i?)-l-[(5')-2-amino-3,3-dimethylbutanoyl]- 4-hydroxy-N-[(5) -(4-(4-methylthiazol-5-yl)phenyl)ethyl]-pyrrolidine-2-carboxamide hydrochloride (UTM-2, 920 mg,1.91 mmol), DIPEA (1.05 g, 8.11 mmol), HATU (1.85 g, 4.87 mmol) in anhydrous N,N-dimethylformamide (8 mL) at 0°C, the resulting mixture was stirred at room temperature for 20 min. LC-MS showed the reaction was completed. The mixture was partitioned between ethyl acetate (60 mL) and water (30 mL). The aqueous layer was extracted with ethyl acetate (30 mL x 2). The combined organic layers were collected, washed with brine (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by preparative HPLC to afford the title compound in Example 77 (404.1 mg, yield 32%) as white solid. H NMR (400 MHz, CD3OD): δ 1.06 (s, 9H), 1.51 & 1.59 (d, J = 6.8 Hz, 3H), 1.72 (s, 3H), 1. 93-2.00 (m, 3H), 2.20-2.25 (m, IH), 2.46 (s, 3H), 2.49 (s, 3H), 2.71 (s, 3H), 3.45-3.67 (m, 10H), 3.75-3.78 (m, IH), 3.85-3.88 (m, IH), 3.95-4.05 (m, 2H), 4.45 (br, IH), 4.59-4.71 (m, 3H), 4.99-5.04 (m, IH), 7.40-7.49 (m, 8H), 7.57 (d, J = 9.6 Hz, IH), 8.89 (s, IH); LC-MS (ES+): m/z 986.4/988.4 [M+H+]
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