Alternatived Products of [ 1272412-72-2 ]
Product Details of [ 1272412-72-2 ]
CAS No. : | 1272412-72-2 |
MDL No. : | MFCD18782894 |
Formula : |
C10H18N2O2
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | WDVOLHDNUMLNAK-UHFFFAOYSA-N |
M.W : | 198.26 g/mol |
Pubchem ID : | 56828077 |
Synonyms : |
|
Safety of [ 1272412-72-2 ]
Application In Synthesis of [ 1272412-72-2 ]
* 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 [ 1272412-72-2 ]
- 1
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(S)-N-(4-chloro-2-(2-(5-chloro-6-methylpyrazolo[1,5-a]-pyrimidin-2-yl)piperidine-1-carbonyl)phenyl)methanesulfonamide
[ No CAS ]

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[ 1272412-72-2 ]

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(S)-tert-butyl 1-(2-(1-(5-chloro-2-(methylsulfonamido)benzoyl)piperidin-2-yl)-6-methylpyrazolo[1,5-a]pyrimidin-5-yl)-1,6-diazaspiro[3.3]heptane-6-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
35% |
With triethylamine In methanol at 75℃; |
157
Example 157 Preparation of Compound 42 [1014] Triethylamine (0.100 mL, 0.717 mmol) was added to a mixture of intermediate 11 (71 mg, 0.147 mmol) and tert-butyl 1,6-diazaspiro[3.3]heptane-6-carboxylate (114 mg, 0.575 mmol) in 5 mL of methanol at room temperature. After heating at 75° C. overnight, reaction mixture was cooled to room temperature and concentrated under reduced pressure. The remaining residue was purified by silica gel column chromatography (5-75% ethyl acetate in hexanes) to yield (S)-tert-butyl 1-(2-(1-(5-chloro-2-(methylsulfonamido)benzoyl)piperidin-2-yl)-6-methylpyrazolo[1,5-a]pyrimidin-5-yl)-1,6-diazaspiro[3.3]heptane-6-carboxylate as a solid (33 mg, 35%). This solid was dissolved in 3 mL of dichloromethane and trifluoroacetic acid (0.15 mL, 1.95 mmol) was added. After stirring overnight and reaction mixture was concentrated under reduced pressure to yield compound 42 (33 mg, 99%) as a white solid. [1016] LCMS m/z [M+H]+ C25H30ClN7O3 requires: 544.18. Found 544.37. [1017] HPLC Tr (min), purity %: 5.67, 96%. |
- 2
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[ 1272412-72-2 ]

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1-(2-methoxyphenyl)-6-(3-((4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)thio)propyl)-1,6-diazaspiro[3.3]heptane
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: tris-(dibenzylideneacetone)dipalladium(0); ruphos; sodium t-butanolate / 1,4-dioxane / 0.33 h / 100 °C
2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
3: caesium carbonate / acetonitrile / 12 h / 70 °C |
|
Reference:
[1]Reilly, Sean W.; Griffin, Suzy; Taylor, Michelle; Sahlholm, Kristoffer; Weng, Chi-Chang; Xu, Kuiying; Jacome, Daniel A.; Luedtke, Robert R.; Mach, Robert H.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9905 - 9910]
- 3
-
[ 1272412-72-2 ]

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C12H16N2O
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: tris-(dibenzylideneacetone)dipalladium(0); ruphos; sodium t-butanolate / 1,4-dioxane / 0.33 h / 100 °C
2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C |
|
Reference:
[1]Reilly, Sean W.; Griffin, Suzy; Taylor, Michelle; Sahlholm, Kristoffer; Weng, Chi-Chang; Xu, Kuiying; Jacome, Daniel A.; Luedtke, Robert R.; Mach, Robert H.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9905 - 9910]
- 4
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[ 1272412-72-2 ]

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C11H13FN2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: tris-(dibenzylideneacetone)dipalladium(0); ruphos; sodium t-butanolate / 1,4-dioxane / 0.33 h / 100 °C
2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C |
|
Reference:
[1]Reilly, Sean W.; Griffin, Suzy; Taylor, Michelle; Sahlholm, Kristoffer; Weng, Chi-Chang; Xu, Kuiying; Jacome, Daniel A.; Luedtke, Robert R.; Mach, Robert H.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9905 - 9910]
- 5
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[ 1272412-72-2 ]

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1-(4-fluorophenyl)-6-(3-((4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)thio)propyl)-1,6-diazaspiro[3.3]heptane
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: tris-(dibenzylideneacetone)dipalladium(0); ruphos; sodium t-butanolate / 1,4-dioxane / 0.33 h / 100 °C
2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
3: caesium carbonate / acetonitrile / 12 h / 70 °C |
|
Reference:
[1]Reilly, Sean W.; Griffin, Suzy; Taylor, Michelle; Sahlholm, Kristoffer; Weng, Chi-Chang; Xu, Kuiying; Jacome, Daniel A.; Luedtke, Robert R.; Mach, Robert H.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9905 - 9910]
- 6
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[ 1272412-72-2 ]

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C17H24N2O3
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos In 1,4-dioxane at 100℃; for 0.333333h; |
|
Reference:
[1]Reilly, Sean W.; Griffin, Suzy; Taylor, Michelle; Sahlholm, Kristoffer; Weng, Chi-Chang; Xu, Kuiying; Jacome, Daniel A.; Luedtke, Robert R.; Mach, Robert H.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9905 - 9910]
- 7
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[ 1272412-72-2 ]

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C16H21FN2O2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos In 1,4-dioxane at 100℃; for 0.333333h; |
|
Reference:
[1]Reilly, Sean W.; Griffin, Suzy; Taylor, Michelle; Sahlholm, Kristoffer; Weng, Chi-Chang; Xu, Kuiying; Jacome, Daniel A.; Luedtke, Robert R.; Mach, Robert H.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9905 - 9910]
- 8
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[ 763114-26-7 ]

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[ 1272412-72-2 ]

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tert-butyl 1-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)-methyl)benzoyl)-1,6-diazaspiro[3.3]heptane-6-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
98% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 60℃; for 12h; |
|
Reference:
[1]Reilly, Sean W.; Puentes, Laura N.; Wilson, Khadija; Hsieh, Chia-Ju; Weng, Chi-Chang; Makvandi, Mehran; Mach, Robert H.
[Journal of Medicinal Chemistry, 2018, vol. 61, # 12, p. 5367 - 5379]
- 9
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[ 1272412-72-2 ]

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4-(4-fluoro-3-(1,6-diazaspiro[3.3]heptane-1-carbonyl)benzyl)-phthalazin-1(2H)-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / tetrahydrofuran / 12 h / 60 °C
2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C |
|
Reference:
[1]Reilly, Sean W.; Puentes, Laura N.; Wilson, Khadija; Hsieh, Chia-Ju; Weng, Chi-Chang; Makvandi, Mehran; Mach, Robert H.
[Journal of Medicinal Chemistry, 2018, vol. 61, # 12, p. 5367 - 5379]
- 10
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[ 1272412-72-2 ]

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4-(3-(6-(cyclopropanecarbonyl)-1,6-diazaspiro[3.3]heptane-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2H)-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / tetrahydrofuran / 12 h / 60 °C
2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / tetrahydrofuran / 12 h / 60 °C |
|
Reference:
[1]Reilly, Sean W.; Puentes, Laura N.; Wilson, Khadija; Hsieh, Chia-Ju; Weng, Chi-Chang; Makvandi, Mehran; Mach, Robert H.
[Journal of Medicinal Chemistry, 2018, vol. 61, # 12, p. 5367 - 5379]
- 11
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[ 1272412-72-2 ]

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[ 407-25-0 ]

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tert-butyl 1-(2,2,2-trifluoroacetyl)-1,6-diazaspiro[3.3]heptane-6-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
81% |
With triethylamine In dichloromethane at 0 - 25℃; for 18h; |
|
Reference:
[1]Bosset, Cyril; Beucher, Hélène; Bretel, Guillaume; Pasquier, Elisabeth; Queguiner, Laurence; Henry, Cyril; Vos, Ann; Edwards, James P.; Meerpoel, Lieven; Berthelot, Didier
[Organic Letters, 2018, vol. 20, # 19, p. 6003 - 6006]
- 12
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[ 1272412-72-2 ]

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tert-butyl 5-(2-methylquinolin-4-yl)-1-(2,2,2-trifluoroacetyl)-1,6-diazaspiro[3.3]heptane-6-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 18 h / 0 - 25 °C
2: [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; trifluoroacetic acid; sodium persulfate / acetonitrile; water / 30 h / 20 - 25 °C / Sealed tube; Inert atmosphere; Irradiation |
|
Reference:
[1]Bosset, Cyril; Beucher, Hélène; Bretel, Guillaume; Pasquier, Elisabeth; Queguiner, Laurence; Henry, Cyril; Vos, Ann; Edwards, James P.; Meerpoel, Lieven; Berthelot, Didier
[Organic Letters, 2018, vol. 20, # 19, p. 6003 - 6006]
- 13
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[ 1272412-72-2 ]

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[ 5783-36-8 ]

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C24H28N2O4
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h; |
Step a). Tert-butyl 3-(3'-methoxy-[1,1'-biphenyl]-4-carboxamido)azetidine-1-carboxylate45.
General procedure: To a stirred solution of 3'-methoxy-[1,1'-biphenyl]-4-carboxylic acid (228 mg, 1 mmol),and tert-butyl 3-amino-3-methylazetidine-1-carboxylate (189.2 mg, 1.02 mmol.) and N,Ndiisopropyl-ethylamine (452.4 mg, 3.5 mmol) in DMF (5 mL) was added HBTU (1.32g, 3.48mmol). The resulting mixture was stirred at room temperature for 18 hours. The reactionmixture was partitioned between water (30 mL) and ethyl acetate (30 mL) and the aqueouslayer was extracted with ethyl acetate (50 mL). The combined organic extracts were washedwith saturated NaHCO3 (30 mL), and brine (30 mL). The organic layer was dried overNa2SO4 and concentrated under reduced pressure. The residue was purified on silica gel(Biotage; eluting solvents hexane: EtOAc 4/1 ratio) to afford tert-butyl 3-(3'-methoxy-[1,1'-biphenyl]-4-carboxamido)-3-methylazetidine-1-carboxylate as a colorless solid in 80% yield. |
Reference:
[1]Malamas, Michael S.; Farah, Shrouq I.; Lamani, Manjunath; Pelekoudas, Dimitrios N.; Perry, Nicholas Thomas; Rajarshi, Girija; Miyabe, Christina Yume; Chandrashekhar, Honrao; West, Jay; Pavlopoulos, Spiro; Makriyannis, Alexandros
[Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]
- 14
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[ 1272412-72-2 ]

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C19H20N2O2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C
2: trifluoroacetic acid / dichloromethane / 6 h / 20 °C |
|
Reference:
[1]Malamas, Michael S.; Farah, Shrouq I.; Lamani, Manjunath; Pelekoudas, Dimitrios N.; Perry, Nicholas Thomas; Rajarshi, Girija; Miyabe, Christina Yume; Chandrashekhar, Honrao; West, Jay; Pavlopoulos, Spiro; Makriyannis, Alexandros
[Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]
- 15
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[ 1272412-72-2 ]

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C18H20N2O3S
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C
2: trifluoroacetic acid / dichloromethane / 6 h / 20 °C |
|
Reference:
[1]Malamas, Michael S.; Farah, Shrouq I.; Lamani, Manjunath; Pelekoudas, Dimitrios N.; Perry, Nicholas Thomas; Rajarshi, Girija; Miyabe, Christina Yume; Chandrashekhar, Honrao; West, Jay; Pavlopoulos, Spiro; Makriyannis, Alexandros
[Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]
- 16
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[ 1272412-72-2 ]

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1-(3'-methoxy-[1,1'-biphenyl]-4-carbonyl)-1,6-diazaspiro[3.3]heptane-6-carbonitrile
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C
2.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C
3.1: triethylamine / dichloromethane
3.2: 20 °C |
|
Reference:
[1]Malamas, Michael S.; Farah, Shrouq I.; Lamani, Manjunath; Pelekoudas, Dimitrios N.; Perry, Nicholas Thomas; Rajarshi, Girija; Miyabe, Christina Yume; Chandrashekhar, Honrao; West, Jay; Pavlopoulos, Spiro; Makriyannis, Alexandros
[Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]
- 17
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[ 1272412-72-2 ]

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1-((3'-methoxy-[1,1'-biphenyl]-4-yl)sulfonyl)-1,6-diazaspiro[3.3]heptane-6-carbonitrile
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C
2.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C
3.1: triethylamine / dichloromethane
3.2: 20 °C |
|
Reference:
[1]Malamas, Michael S.; Farah, Shrouq I.; Lamani, Manjunath; Pelekoudas, Dimitrios N.; Perry, Nicholas Thomas; Rajarshi, Girija; Miyabe, Christina Yume; Chandrashekhar, Honrao; West, Jay; Pavlopoulos, Spiro; Makriyannis, Alexandros
[Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]
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[ 1272412-72-2 ]

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3'-methoxy-[1,1'-biphenyl]-4-sulfonyl chloride
[ No CAS ]

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C23H28N2O5S
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h; |
Step a). Tert-butyl 3-(3'-methoxy-[1,1'-biphenyl]-4-carboxamido)azetidine-1-carboxylate 45.
General procedure: To a stirred solution of 3'-methoxy-[1,1'-biphenyl]-4-carboxylic acid (228 mg, 1 mmol),and tert-butyl 3-amino-3-methylazetidine-1-carboxylate (189.2 mg, 1.02 mmol.) and N,Ndiisopropyl-ethylamine (452.4 mg, 3.5 mmol) in DMF (5 mL) was added HBTU (1.32g, 3.48mmol). The resulting mixture was stirred at room temperature for 18 hours. The reactionmixture was partitioned between water (30 mL) and ethyl acetate (30 mL) and the aqueouslayer was extracted with ethyl acetate (50 mL). The combined organic extracts were washedwith saturated NaHCO3 (30 mL), and brine (30 mL). The organic layer was dried overNa2SO4 and concentrated under reduced pressure. The residue was purified on silica gel(Biotage; eluting solvents hexane: EtOAc 4/1 ratio) to afford tert-butyl 3-(3'-methoxy-[1,1'-biphenyl]-4-carboxamido)-3-methylazetidine-1-carboxylate as a colorless solid in 80% yield. |
Reference:
[1]Malamas, Michael S.; Farah, Shrouq I.; Lamani, Manjunath; Pelekoudas, Dimitrios N.; Perry, Nicholas Thomas; Rajarshi, Girija; Miyabe, Christina Yume; Chandrashekhar, Honrao; West, Jay; Pavlopoulos, Spiro; Makriyannis, Alexandros
[Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]
- 19
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[ 1272412-72-2 ]

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C6H12N2*2C2HF3O2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride / lithium hydroxide monohydrate / 16 h / 20 °C / Inert atmosphere
2: 1 h / 0 °C |
|
|
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride; methanol / lithium hydroxide monohydrate / 16 h / 20 °C / Inert atmosphere
2: dichloromethane / 1 h / 0 °C |
|
- 20
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[ 67-56-1 ]

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[ 50-00-0 ]

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[ 1272412-72-2 ]

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tert-butyl 1-methyl-1,6-diazaspiro[3.3]heptane-6-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
56% |
With sodium tris(acetoxy)borohydride In lithium hydroxide monohydrate at 20℃; for 16h; Inert atmosphere; |
Step A.
A mixture of tert-butyl 1,6-diazaspiro[3.3]heptane-6-carboxylate (0.5 g, 2.52 mmol), formaldehyde aqueous solution (37%) (2 g, 25.25 mmol) and sodium triacetoxyborohydride (1.6 g, 7.56 mmol) in MeOH (20 mL) was stirred for 16 h at rt under N2. The mixture was diluted with DCM (50 mL), the organic layer was washed with water and sodium bicarbonate solution, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluting with PE/EA = 2:1) to give tert- butyl 1-methyl-1,6-diazaspiro[3.3]heptane-6-carboxylate (300 mg, 56 % yield) as an oil. Mass Spectrum (ESI) m/z = 213 (M+1). |
56% |
With sodium tris(acetoxy)borohydride In lithium hydroxide monohydrate at 20℃; for 16h; Inert atmosphere; |
Step A.
A mixture of tert-butyl 1,6-diazaspiro[3.3]heptane-6-carboxylate (0.5 g, 2.52 mmol), formaldehyde aqueous solution (37%) (2 g, 25.25 mmol) and sodium triacetoxyborohydride (1.6 g, 7.56 mmol) in MeOH (20 mL) was stirred for 16 h at rt under N2. The mixture was diluted with DCM (50 mL), the organic layer was washed with water and sodium bicarbonate solution, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluting with PE/EA = 2:1) to give tert- butyl 1-methyl-1,6-diazaspiro[3.3]heptane-6-carboxylate (300 mg, 56 % yield) as an oil. Mass Spectrum (ESI) m/z = 213 (M+1). |
- 21
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[ 50-00-0 ]

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[ 1272412-72-2 ]

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tert-butyl 1-methyl-1,6-diazaspiro[3.3]heptane-6-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
56% |
With methanol; sodium tris(acetoxy)borohydride In lithium hydroxide monohydrate at 20℃; for 16h; Inert atmosphere; |
Step A.
A mixture of tert-butyl 1,6-diazaspiro[3.3]heptane-6-carboxylate (0.5 g, 2.52 mmol), formaldehyde aqueous solution (37%) (2 g, 25.25 mmol) and sodium triacetoxyborohydride (1.6 g, 7.56 mmol) in MeOH (20 mL) was stirred for 16 h at rt under N2. The mixture was diluted with DCM (50 mL), the organic layer was washed with water and sodium bicarbonate solution, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluting with PE/EA = 2:1) to give tert- butyl 1-methyl-1,6-diazaspiro[3.3]heptane-6-carboxylate (300 mg, 56 % yield) as an oil. Mass Spectrum (ESI) m/z = 213 (M+1). |