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[ CAS No. 1038916-11-8 ] {[proInfo.proName]}

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Chemical Structure| 1038916-11-8
Chemical Structure| 1038916-11-8
Structure of 1038916-11-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1038916-11-8 ]

CAS No. :1038916-11-8 MDL No. :MFCD26383933
Formula : C24H28N4O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 420.50 Pubchem ID :-
Synonyms :

Safety of [ 1038916-11-8 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1038916-11-8 ]

* 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 [ 1038916-11-8 ]

[ 1038916-11-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1038916-11-8 ]
  • [ 104-15-4 ]
  • [ 1038915-73-9 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; water; at 66℃;Product distribution / selectivity; Step 4; (35)-3-{4-[7-(Arainocarbonyl)-2H-indazol-2-yl]phenyl}piperidinium 4- methylbenzenesulfonate (D4); (D3) was dissolved in THF (0.15M) and water added (5% compared to THF). para- Toluene sulphonic acid monohydrate (2.2 eq.) was added and the mixture heated to 66 0C and stirred overnight. After cooling the desired solid salt was isolated by filtration and confirmed to be a monohydrate (D4). 1H NMR (400 MHz, DMSO, 300K) delta 9.34 (IH, s); 9.20 (IH, broad s), 8.58 (IH, s), 8.14 (2H, d, J=8.8 Hz), 8.05 (2H, ddd, J=1.2, 7.2, 16.8 Hz), 7.93 (IH, s), 7.52 (4H, dd, J=8.8, 16.8 Hz), 7.27 (IH, dd, J=6.8, 8.0 Hz), 7.13 (2H, d, J=8 Hz), 3.48 (3H, m), 3.10 (2H, m), 2.90 (IH, m); 2.30 (3H, s), 1.89 (2H, m), 1.75 (2H, m).
12.5 g In tetrahydrofuran; water; at 65 - 67℃;Inert atmosphere; To a solution of tert-butyl (S)-3-(4-(7-carbamoyl-2H-indazol-2-yl) phenyl)piperidine-l-carboxylate (Compound 22) (15.78 g) in THF (220 mL) and water (11.92 mL), p-toluene sulphonic acid monohydrate (16.14 g) was added under nitrogen atmosphere. The reaction mixture was heated to 65-67C and stirred for 16 h or until HPLC/TLC analysis indicated completion of the reaction. After completion of reaction, the slurry was cooled to room temperature, filtered and washed with THF (30 mL). The solid was collected and dried in vacuum at 40C to afford the titled compound as tan-colored solid (Yield: 12.5 g; HPLC Purity: 97.34%).NMR (400 MHz, CDCh): delta 1.85-1.81 (m, 2H), 2.09-2.05 (m, 2H), 2.34 (s, 3H), 3.16-3.04(m,3H), 3.49-3.32 (m,2H), 7.25-7.23 (2H, d,), 7.28-7.26 (2H, d,), 7.51-7.49 (2H, d,), 8.11-7.95 (m, 3H), 8.22-8.15 (dd,lH), 9.02(s,lH). 13C NMR (100 MHz, CDCh): delta 19.91, 22.43, 29.32, 39.49, 43.65, 120.41, 120.78, 121.69, 122.68, 123.85, 125.56, 125.82, 128.22, 128.49, 130.24, 138.90, 140.42, 141.52, 142.07, 146.51, 168.13.
  • 2
  • [ 1171197-20-8 ]
  • [ 1038916-11-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: ammonia / methanol / 60 °C
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: ammonia / methanol / 60 °C
Multi-step reaction with 3 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: ammonia / methanol / 60 °C
Multi-step reaction with 3 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: ammonia / methanol / 60 °C
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: ammonia / methanol / 60 °C
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 4: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: ammonia / methanol / 60 °C
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 4: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 5 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 5 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 5 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 5 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 6 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C 5: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 6: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 6 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C 5: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 6: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 2 steps 1: isopropyl alcohol / 74 - 82 °C / Inert atmosphere 2: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere

Reference: [1]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[2]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[3]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[4]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[5]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[6]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[7]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[8]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[9]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[10]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[11]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[12]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[13]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[14]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[15]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2019/36441, 2019, A1
  • 4
  • [ 5471-82-9 ]
  • [ 1038916-11-8 ]
Reference: [1]Organic Process Research and Development,2011,vol. 15,p. 831 - 840
[2]Organic Process Research and Development,2011,vol. 15,p. 831 - 840
[3]Organic Process Research and Development,2011,vol. 15,p. 831 - 840
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[41]Organic Process Research and Development,2011,vol. 15,p. 831 - 840
[42]Organic Process Research and Development,2011,vol. 15,p. 831 - 840
[43]Patent: WO2019/36441,2019,A1
[44]Patent: WO2019/36441,2019,A1
[45]Patent: WO2019/36441,2019,A1
[46]Patent: WO2019/36441,2019,A1
  • 5
  • [ 19733-56-3 ]
  • [ 1038916-11-8 ]
Reference: [1]Organic Process Research and Development,2011,vol. 15,p. 831 - 840
[2]Organic Process Research and Development,2011,vol. 15,p. 831 - 840
[3]Organic Process Research and Development,2011,vol. 15,p. 831 - 840
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  • 7
  • [ 1171197-20-8 ]
  • 3-formyl-2-nitrobenzamide [ No CAS ]
  • [ 1038916-11-8 ]
YieldReaction ConditionsOperation in experiment
2.8 g Stage #1: (3S)-3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester; 3-formyl-2-nitrobenzamide In ethanol for 2h; Inert atmosphere; Reflux; Stage #2: With 2,6-dimethylpyridine In ethanol; N,N-dimethyl-formamide Stage #3: With sodium azide In N,N-dimethyl-formamide at 110℃; for 20h; 3D Example 3 (D): Preparation of tert-butyl (S)-3-(4-(7-carbamoyl-2H-indazol-2-yl) phenyl)piperidine-l-carboxylate (Compound Va) (Compound V, R5 is H and R6 is Boc=Compound 22) 3-Formyl-2-nitrobenzamide (Compound 11) (3.5 g), tert-butyl (S)- 3-(4-aminophenyl) piperidine-l-carboxylate (Compound 21) (4.98 g) and ethanol (30 mL) were charged to a round bottomed flask under inert atmosphere and heated to reflux temperature for 2 h or until HPLC/TLC analysis indicated completion of the reaction. DMF (50 mL) and lutidine (2.5 mL) was added to reaction mass to give a clear solution. Ethanol was distilled off and sodium azide (1.72 g) was added. The reaction mass was heated to 110°C for 20 h or until HPLC/TLC analysis indicated completion of the reaction. The reaction mass was cooled to 25°C, THF (200 mL) was added followed by addition of 25% aq. LiCl solution (100 mL, precooled at 5°C) and the layers were separated. The aqueous layer was re-extracted twice with THF (2x50 mL). The organic layers were combined and washed twice with 25% aq. LiCl solution (30 mL). It was passed through small silica bed using MTBE:DCM (1 : 1) (500 mL). Solvent was removed under vacuum till 1-2 volume was left. Reaction mass was cooled to 0-10°C for 2 h. The solid obtained was filtered and suck dried to afford the titled compound as off-white solid (Yield: 2.8 g; HPLC Purity: 98 %).
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