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[ CAS No. 102169-54-0 ] {[proInfo.proName]}

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Chemical Structure| 102169-54-0
Chemical Structure| 102169-54-0
Structure of 102169-54-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 102169-54-0 ]

CAS No. :102169-54-0 MDL No. :MFCD18839147
Formula : C6H12ClN Boiling Point : -
Linear Structure Formula :- InChI Key :CBCZSSUFAOAUMP-UHFFFAOYSA-N
M.W : 133.62 Pubchem ID :71756008
Synonyms :

Calculated chemistry of [ 102169-54-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.79
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.38
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 1.74
Log Po/w (SILICOS-IT) : 0.87
Consensus Log Po/w : 1.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.34
Solubility : 6.11 mg/ml ; 0.0457 mol/l
Class : Very soluble
Log S (Ali) : -1.53
Solubility : 3.95 mg/ml ; 0.0295 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.14
Solubility : 9.7 mg/ml ; 0.0726 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.32

Safety of [ 102169-54-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 102169-54-0 ]

* 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 [ 102169-54-0 ]

[ 102169-54-0 ] Synthesis Path-Downstream   1~43

  • 2
  • [ 14918-21-9 ]
  • [ 102169-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 41 percent / LiAlH4 / diethyl ether / Heating 2: 91 percent / HCl / diethyl ether
  • 3
  • N-9-fluorenylmethyloxycarbonyl-4-benzoyl-D-phenylalanine [ No CAS ]
  • [ 41624-92-4 ]
  • [ 102169-54-0 ]
  • C31H38N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multistep reaction.;
  • 4
  • [ 41624-92-4 ]
  • [ 102169-54-0 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • C31H38N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multistep reaction.;
  • 5
  • [ 41624-92-4 ]
  • [ 102169-54-0 ]
  • 2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
  • [ 185116-43-2 ]
  • C38H43N3O6 [ No CAS ]
  • 6
  • [ 6097-08-1 ]
  • [ 102169-54-0 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 2-(hex-5-yn-1-yl)isoindole-1,3-dione With hydrazine hydrate In ethanol for 1h; Reflux; Stage #2: With hydrogenchloride In water Synthesis of 5-hexyn-1-amine A solution of N-(5-hexynyl)phthalimide (1140mg, 5.0 mmol) and hydrazine hydrate (1.2 mL, 20 mmol) in ethanol (20 mL) wasstirred in reflux for 1 hour, and then cooled to room temperature. The mixturewas poured into water (100 mL), pH of the solution was adjusted above 10, andthe mixture was extracted with ethyl acetate (6 × 50 mL). The organic layer wasconcentrated in vacuo after the addition of aqueous hydrochloride,5-hexyn-1-amine was obtained as a hydrochloride salt. (550 mg, 4.1 mmol, yield82 % ) 1H NMR (400 MHz, D2O) δ 2.94 (t, J = 7.5 Hz, 2H),2.28 (t, J = 2.6 Hz, 1H), 2.18 (m, 2H), 1.69 (m, 2H), 1.51 (m, 2H). 13CNMR (100 MHz, D2O) δ 85.13, 69.68, 39.04, 25.81, 24.49, 17.10
32.8 g Stage #1: 2-(hex-5-yn-1-yl)isoindole-1,3-dione With hydrazine hydrate In tetrahydrofuran for 6h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 25℃; Inert atmosphere; Reflux;
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / water; isopropyl alcohol / 20 °C / Inert atmosphere 2: hydrogenchloride / diethyl ether / Inert atmosphere
Stage #1: 2-(hex-5-yn-1-yl)isoindole-1,3-dione With hydrazine hydrate In methanol at 80℃; for 2h; Stage #2: With hydrogenchloride In methanol; water at 25 - 80℃;

  • 8
  • [ 918106-28-2 ]
  • [ 102169-54-0 ]
  • [ 1227736-77-7 ]
YieldReaction ConditionsOperation in experiment
31% With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 70℃; for 17h; Inert atmosphere;
  • 9
  • C13H11FN2O2 [ No CAS ]
  • [ 102169-54-0 ]
  • [ 1338494-74-8 ]
YieldReaction ConditionsOperation in experiment
100 mg With N-ethyl-N,N-diisopropylamine; HATU In dimethyl sulfoxide
  • 10
  • [ 622398-31-6 ]
  • [ 102169-54-0 ]
  • 1-(2-nitrophenyl)ethyl hex-5-yn-1-yl carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With triethanolamine In dichloromethane at 20℃; for 2h; 2 4.2
Synthesis of 1-(2-nitrophenyl)ethyl hex-5-yn-1-yl carbamate (3) To a solution of 1-(2-nitrophenyl)ethyl N-succinimidyl carbonate (see Supplementary data ) (1.02 g, 3.0 mmol) in DCM (15 mL), was added TEA (1.70 ml, 12.0 mmol) and 5-hexyn-1-amine hydrochloride (see Supplementary data ) (400 mg, 3.0 mmol). The mixtrue solution was stirred at room temperature for 2 h and was then diluted with DCM (100 mL). The organic layer was washed with brine (3 * 50 mL), dried over Na2SO4. After concentration in vacuo, the residue was purified by short silica gel column with petroleum ether:ethyl acetate (1:1) to give 3 as a clear, yellow oil (670 mg, 2.3 mmol, yield 77%). 1 H NMR (400 MHz, CDCl3) δ 7.90 (d, J = 8 Hz, 1H), 7.61 (d, J = 4 Hz, 2H), 7.44-7.34 (m, 1H), 6.22 (q, J = 6 Hz, 1H), 3.14 (m, 2H), 2.20 (m, 2H), 1.94 (t, J = 6 Hz, 1H), 1.60 (q, J = 6 Hz, 3H), 1.55-1.46 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 155.32, 147.61, 138.78, 133.48, 128.15, 127.05, 124.39, 83.97, 68.71, 68.52, 40.44, 28.95, 25.47, 22.24, 18.05.
  • 11
  • [ 99-60-5 ]
  • [ 102169-54-0 ]
  • [ 1570114-41-8 ]
YieldReaction ConditionsOperation in experiment
84% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4h;
  • 12
  • [ 2516-96-3 ]
  • [ 102169-54-0 ]
  • [ 1570114-43-0 ]
YieldReaction ConditionsOperation in experiment
62% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h;
  • 13
  • [ 1493802-05-3 ]
  • [ 102169-54-0 ]
  • [ 75-64-9 ]
  • C63H69N9O12*2C4H11N*C6H11N [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene Inert atmosphere;
  • 14
  • [ 1493802-05-3 ]
  • [ 102169-54-0 ]
  • [ 1493802-09-7 ]
YieldReaction ConditionsOperation in experiment
88% In toluene at 90℃; for 6h; Inert atmosphere;
  • 15
  • [ 14918-21-9 ]
  • [ 102169-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris(pentafluorophenyl)borate / chloroform-d1 / 0.17 h / 25 °C / Inert atmosphere 2: hydrogenchloride; water / diethyl ether / 1 h / 20 °C
  • 16
  • C14H31NSi2 [ No CAS ]
  • [ 102169-54-0 ]
YieldReaction ConditionsOperation in experiment
64 mg With hydrogenchloride; water In diethyl ether at 20℃; for 1h;
  • 17
  • (E)-2-(2-iodovinyl)benzoic acid [ No CAS ]
  • [ 102169-54-0 ]
  • (E)-N-(5-hexyn-1-yl)-2-(2-iodovinyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
  • 18
  • [ 102169-54-0 ]
  • (E)-N-(5-hexyn-1-yl)-2-(2-iodovinyl)-N-(4-methoxybenzyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / methanol / 3.17 h / 0 - 20 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C / Inert atmosphere
  • 19
  • [ 102169-54-0 ]
  • (7Z,9E)-2-(4-methoxybenzyl)-3,4,5,6-tetrahydrobenzo[c][1]azacyclododecin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / methanol / 3.17 h / 0 - 20 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C / Inert atmosphere 4: (R)-(-)-4,12-bis(diphenylphosphino)-[2,2]-paracyclophane; potassium carbonate; copper diacetate; sodium formate / N,N-dimethyl-formamide / 3.5 h / 120 °C / Inert atmosphere
  • 20
  • [ 102169-54-0 ]
  • 1-[N-(4-methoxybenzyl)amino]-5-hexyne [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / methanol / 3.17 h / 0 - 20 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere
  • 21
  • [ 102169-54-0 ]
  • [ 123-11-5 ]
  • C14H17NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In methanol at 0 - 20℃; for 3.16667h; Inert atmosphere;
  • 22
  • C34H40F17N2O3P [ No CAS ]
  • [ 102169-54-0 ]
  • 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl N-(3-(3-(hex-5-yn-1-yl)ureido)benzoyl)-N-(prop-2-yn-1-yl)glycinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.76 g With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide
  • 23
  • C34H40F17N2O3P [ No CAS ]
  • [ 102169-54-0 ]
  • C20H21N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide 2: pyridine; copper diacetate / 4 h / 90 °C / Microwave irradiation
  • 24
  • [ 928-90-5 ]
  • [ 102169-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pyridine / dichloromethane / 0 h / 18 °C 2.1: sodium azide / N,N-dimethyl-formamide; diethyl ether / 0.08 h / 20 °C 2.2: 5.5 h 2.3: pH 1
Multi-step reaction with 2 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C 2.1: hydrazine hydrate / methanol / 2 h / 80 °C 2.2: 25 - 80 °C
  • 25
  • [ 76911-01-8 ]
  • [ 102169-54-0 ]
YieldReaction ConditionsOperation in experiment
1 g Stage #1: 5-hexynyl p-toluenesulfonate With sodium azide In diethyl ether; N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: With triphenylphosphine In tetrahydrofuran; water for 5.5h; Stage #3: With hydrogenchloride In water
  • 26
  • [ 102169-54-0 ]
  • 4-methyl-N-(5-methylenehept-6-enyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 25 °C 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / 25 °C / 15514.9 Torr / Inert atmosphere
  • 27
  • [ 102169-54-0 ]
  • 4-methyl-N-(4-(7-methyl-5-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)butyl)benzenesulfonamide [ No CAS ]
  • 4-methyl-N-(4-(7-methyl-5-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)butyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 - 25 °C 2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / 25 °C / 15514.9 Torr / Inert atmosphere 3.1: ethylaluminum dichloride / dichloromethane; toluene / 0.58 h / 0 - 25 °C 3.2: 48 h / 25 °C / Darkness
  • 28
  • 3-((4-(((tert-butoxycarbonyl)amino)methyl)-6-(trifluoromethyl)-pyridin-2-yl)oxy)benzoic acid [ No CAS ]
  • [ 102169-54-0 ]
  • tert-butyl ((2-(3-(hex-5-yn-1-ylcarbamoyl)phenoxy)-6-(trifluoromethyl)pyridin-4-yl)methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 3-((4-(((tert-butoxycarbonyl)amino)methyl)-6-(trifluoromethyl)-pyridin-2-yl)oxy)benzoic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.333333h; Stage #2: hex-5-yn-1-amine monohydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3.2h; Synthesis of Int-C To a stirred solution of Int-A (600 mg, 1.45 mmol) in DCM (10 mL) at RT, was added HATU (633 mg, 1.67 mmol) and the mixture was stirred at RT for 20 min. Hex-5-yn-1-amine hydrochloride (214 ^L, 1.6 mmol) and DIEA (430 mg, 3.33 mmol) were added, and the mixture stirred at RT for 3.2 h. The reaction mixture was diluted with a mixture of water and brine. The mixture was repeatedly extracted with EtOAc and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue was purified (silica gel; eluting with 0-100% EtOAc in hexanes), to afford compound Int-C (610 mg, 86%) as a white solid.1H NMR (300 MHz, DMSO-d6): δ 8.52 (m, 1H), 7.74 (m, 1H), 7.50- 7.63 (m, 4H), 7.34 (m, 1H), 7.08 (s, 1H), 4.20- 4.28 (m, 2H), 3.20- 3.28 (m, 2H), 2.74 (m, 1H), 2.10- 2.20 (m, 2H), 1.40- 1.62 (m, 4H), 1.35 (s, 9H).
  • 29
  • [ 331-39-5 ]
  • [ 102169-54-0 ]
  • C15H17NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 27℃; for 18h; 5.2.2 Representative procedure B for 81 Cu(I)-catalyzed (3+2) cycloaddition of alkyne and azide General procedure: The coupling reaction of 82 3,4-dihydroxycinnamic acid (540mg, 3.0mmol) with 83 propargylamine (198mg, 3.6mmol) was performed in the presence of EDCI, 84 HOBt and 85 Et3N in anhydrous 86 DMF at 27°C for 18h to give the 87 caffeic amide 17 (610mg, 93% yield). A solution of 1,4-bis(azidomethyl)benzene [50] (20, 45.2mg, 0.24mmol), CuSO4•5H2O (5.2mg, 0.024mmol), sodium ascorbate (4.8mg, 0.024mmol) and caffeic amide 17 (126mg, 0.58mmol) in H2O/THF (1:1, 10mL) was stirred at 40°C for 12h, and then concentrated under reduced pressure. The residue was washed with water (2×10mL), EtOAc (2×10mL), and CH2Cl2 (2×10mL), and dried under reduced pressure to give compound 7 (102mg, 67% yield).
  • 30
  • [ 102169-54-0 ]
  • 3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-N-(4-(1-(2-(2-(2-(2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)ethoxy)ethoxy) ethoxy)ethyl)-1H-1,2,3-triazol-4-yl)butyl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 30 °C / Inert atmosphere
  • 31
  • [ 102169-54-0 ]
  • 3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-N-(4-(1-(14-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)-3,6,9,12-tetraoxatetradecyl)-1H-1,2,3-triazol-4-yl)butyl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 30 °C / Inert atmosphere
  • 32
  • [ 102169-54-0 ]
  • 3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-N-(4-(1-(4-((2-(2-(2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)ethoxy)ethoxy) ethyl)amino)-4-oxobutyl)-1H-1,2,3-triazol-4-yl)butyl)-4 methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 30 °C / Inert atmosphere
  • 33
  • [ 102169-54-0 ]
  • 3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-4-methyl-N-(4-(1-(4-((2-(2-(2-((2-(1-(2-nitrobenzyl)-2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)ethoxy)ethoxy)ethyl)amino)-4-oxobutyl)-1H-1,2,3-triazol-4-yl)butyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 30 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C / Inert atmosphere
  • 34
  • [ 102169-54-0 ]
  • N-(2-(2-(2-(4-(4-(4-(3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzamido)butyl)-1H-1,2,3-triazol-1-yl)butanamido)ethoxy)ethoxy)ethyl)-2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindoline-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 35 °C / Inert atmosphere
  • 35
  • [ 102169-54-0 ]
  • 3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-N-(4-(1-(4-((6-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)hexyl)amino)-4-oxobutyl)-1H-1,2,3-triazol-4-yl)butyl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 35 °C / Inert atmosphere
  • 36
  • [ 102169-54-0 ]
  • 3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-N-(4-(1-(4-((5-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)pentyl)amino)-4-oxobutyl)-1H-1,2,3-triazol-4-yl)butyl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 35 °C / Inert atmosphere
  • 37
  • [ 102169-54-0 ]
  • 3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-N-(4-(1-(4-((6-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)hexyl)amino)-4-oxobutyl)-1H-1,2,3-triazol-4-yl)butyl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 35 °C / Inert atmosphere
  • 38
  • [ 102169-54-0 ]
  • C49H53BrF2N8O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 35 °C / Inert atmosphere
  • 39
  • [ 102169-54-0 ]
  • C48H50BrF2N9O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 30 °C / Inert atmosphere
  • 40
  • [ 102169-54-0 ]
  • 3-(3-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-4-methyl-N-(4-(1-(4-((4-((2-(1-methyl-2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)butyl)amino)-4-oxobutyl)-1H-1,2,3-triazol-4-yl)butyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 30 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 22 h / 60 °C / Inert atmosphere
  • 41
  • [ 102169-54-0 ]
  • C50H53BrF2N8O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 0 °C 2.1: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 35 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 22 h / 60 °C / Inert atmosphere
  • 42
  • [ 586379-64-8 ]
  • [ 102169-54-0 ]
  • 3-(5-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-N-(hex-5-yn-1-yl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 3-(5-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoic acid With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: hex-5-yn-1-amine monohydrochloride With triethylamine In N,N-dimethyl-formamide at 0℃; General procedure D. Amide formation. General procedure: The carboxylic acid (1.00 equiv) was dissolved in anhydrous DMF, cooled to 0°C, then added Oxyma (ethyl cyanohydroxyiminoacetate) (1.66 equiv.) and DIC (N,N′-diisopropylcarbodiimide) (1.66 equiv.). After 15 min the solution turned yellow, then NEt3(1.66 mL) was added, followed by the corresponding amine starting material (1.10 equiv).The reaction was left 18 - 24 h before quenching with water. The mixture was separatedbetween EtOAc and water, then the aqueous layer re-extracted using EtOAc. The combinedorganic layers were washed with brine, dried over MgSO4, and then concentrated by rotary evaporator under reduced pressure. The corresponding crude amide was then purified by flashcolumn chromatography.
  • 43
  • [ 39028-27-8 ]
  • [ 102169-54-0 ]
  • N-(hex-5-yn-1-yl)-2-iodoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 1h;
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