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Chemical Structure| 2450-71-7 Chemical Structure| 2450-71-7

Structure of 2450-71-7

Chemical Structure| 2450-71-7

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Product Citations

Product Citations

Wolfer, Jamison D ; Minkoff, Benjamin B ; Burch, Heather L ; Sussman, Michael R ;

Abstract: Protein footprinting is a useful method for studying protein higher order structure and conformational changes induced by interactions with various ligands via addition of covalent modifications onto the protein. Compared to other methods that provide single amino acid-level structural resolution, such as cryo-EM, X-ray diffraction, and NMR, mass spectrometry (MS)-based methods can be advantageous as they require lower protein amounts and purity. As with other MS-based proteomic methods, such as post-translational modification analysis, enrichment techniques have proven necessary for both optimal sensitivity and sequence coverage when analyzing highly complex proteomes. Currently used reagents for footprinting via covalent labeling, such as hydroxyl radicals and carbodiimide-based methods, do not yet have a suitable enrichment method, limiting their applicability to whole proteome analysis. Here, we report a method for enrichable covalent labeling built upon the GEE/EDC system commonly used to covalently label aspartic acid and glutamic acid residues. Novel labeling reagents containing alkynyl functionality can be "clicked" to any azido-containing molecule with copper-catalyzed azide−alkyne cycloaddition (CuAAC), allowing for enrichment or further labeling. Multiple azide- and alkyne-containing GEE-like molecules were tested, and the most efficient method was determined to be the EDC-facilitated coupling of glycine propargyl amide (GPA) to proteins. The pipeline we report includes clicking via CuAAC to a commercially available biotin-azide containing a photocleavable linker, followed by enrichment using a streptavidin resin and subsequent cleavage under ultraviolet light. The enrichment process was optimized through the screening of clickable amines, coupling reagents, and enrichment scaffolds and methods with pure model proteins and has also been applied to complex mixtures of proteins isolated from the model plant, Arabidopsis thaliana, suggesting that our method may ultimately be used to measure protein conformation on a proteomic scale.

Alternative Products

Product Details of [ 2450-71-7 ]

CAS No. :2450-71-7
Formula : C3H5N
M.W : 55.08
SMILES Code : C#CCN
MDL No. :MFCD00008198
InChI Key :JKANAVGODYYCQF-UHFFFAOYSA-N
Pubchem ID :239041

Safety of [ 2450-71-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H302-H310-H314
Precautionary Statements:P210-P280-P302+P350-P305+P351+P338-P310
Class:3(6.1,8)
UN#:3286
Packing Group:

Computational Chemistry of [ 2450-71-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 4
Num. arom. heavy atoms 0
Fraction Csp3 0.33
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 17.4
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.38
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.43
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.34
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.15
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.37
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.08

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

0.09
Solubility 67.7 mg/ml ; 1.23 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

0.35
Solubility 123.0 mg/ml ; 2.23 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.18
Solubility 83.9 mg/ml ; 1.52 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.94 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

3.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.14

Application In Synthesis of [ 2450-71-7 ]

* 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 [ 2450-71-7 ]

[ 2450-71-7 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 6625-94-1 ]
  • [ 2450-71-7 ]
  • [ 186501-06-4 ]
  • 2
  • [ 38675-10-4 ]
  • [ 2450-71-7 ]
  • N-Boc-D-Phe-Pro-NHCH2CCH [ No CAS ]
  • 3
  • [ 134221-52-6 ]
  • [ 2450-71-7 ]
  • 2,4-Dimethoxy-6-(prop-2-ynylamino)pyrimidine-5-carbaldehyde [ No CAS ]
  • 2,6-Dimethoxy-N-(prop-2-ynyl)-5-[(prop-2-ynylimino)methyl]pyrimidin-4-amine [ No CAS ]
  • 4
  • [ 37905-02-5 ]
  • [ 2450-71-7 ]
  • C15H23NO2 [ No CAS ]
  • 5
  • [ 108-31-6 ]
  • [ 557-24-4 ]
  • [ 2450-71-7 ]
  • [ 209395-32-4 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; In water; acetic anhydride; acetic acid; Example 14 N-propargylmaleimide (22): A solution of maleic anhydride (19, 2.5 g, 25.5 mmol) and propargylamine (20, 1.75 mL, 25.5 mmol) in glacial acetic acid (50 mL) was stirred in the dark overnight. The reaction mixture was concentrated to dryness and the residue was recrystallized from a mixture of isopropyl alcohol and water. This gave 21 (3.079 g, 20.1 mmol, 79%) as white crystals. Compound 21 (1.49 g, 9.70 mmol) was suspended in acetic anhydride (7 mL) and sodium acetate (437 mg, 5.33 mmol) was added. The resulting suspension was stirred at 65 C. for 2 h, cooled down to room temperature, and then poured into ice-cold water (75 mL). The aqueous solution was extracted three times with diethyl ether. The combined organic layers were dried over Na2SO4, filtered, and concentrated. Column chromatography (CH2Cl2/EtOAc=1/1) provided 22 (755 mg, 5.59 mmol, 58%) as an off-white solid. 1H NMR (400 MHz, CDCl3) delta: 2.21 (t, 1H, J=2.6 Hz, ?C-H), 4.30 (d, 2H, J=2.6 Hz, CH2), 6.76 (s, 2H, =C-H).
  • 6
  • [ 64987-85-5 ]
  • [ 2450-71-7 ]
  • [ 1036847-90-1 ]
  • 9
  • [ 141-97-9 ]
  • [ 2450-71-7 ]
  • [ 1721-26-2 ]
  • 10
  • [ 20026-96-4 ]
  • [ 2450-71-7 ]
  • [ 1325714-39-3 ]
  • 11
  • [ 5779-93-1 ]
  • [ 2450-71-7 ]
  • [ 1240718-47-1 ]
  • 12
  • [ 1195771-65-3 ]
  • [ 2450-71-7 ]
  • [ 1371547-96-4 ]
  • 13
  • [ 16883-16-2 ]
  • [ 2450-71-7 ]
  • [ 923804-34-6 ]
  • 14
  • [ 2450-71-7 ]
  • [ 190900-21-1 ]
  • 3-methyl-5,6,8,9-tetrahydro-imidazo[1,2-a][1,4]diazepine-7-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
468 mg In methanol; for 5h;Reflux; 6.01.35.02 3-methyl-5,6,8,9-tetrahydro-imidazo[1,2-a][1,4]diazepine-7-carboxylic acid tert-butyl ester 0.6 mL propargylamin was added to 429 mg <strong>[190900-21-1]5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester</strong> in 20 mL methanol. The reaction was refluxed 5 h and evaporated to give 468 mg of the desired product. (M+H)+: 252, Rt: 0.88 min (method J)
  • 15
  • [ 138165-75-0 ]
  • [ 2450-71-7 ]
  • [ 1454891-37-2 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine; 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 20℃; for 22h;Inert atmosphere; Cooling with ice; General procedure: Alkynylamine (1.5equiv) was added to N-Boc-l-leucine or N-Boc-l-beta-homoleucine (1equiv) and HATU (1.1equiv) in DMF at room temperature under nitrogen. The solutions were cooled on ice and Et3N (3equiv) was added, thereaction mixture was then allowed to reach room temperature and stirred for 22h. The reaction mixture was diluted with EtOAc(30ml), washed with 0.1M HCl (2×10ml), saturated NaHCO3 (10ml), brine (20ml), dried over Na2SO4 and the solvents wereremoved. The crude product was purified by automated flashchromatography (gradient, 0-100% EtOAc in heptane).
  • 16
  • [ 98045-03-5 ]
  • [ 2450-71-7 ]
  • [ 1585205-43-1 ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 1h;Inert atmosphere; Boc-L-Asp(OMe)-OH 15 (2 g,8.1 mmol) and 40 mL DCM were taken in a 100 mL round bottom flask and cooled at0C. To this solution DCC (1.67 g, 8.1 mmol) and propargylamine (450 mg, 8.1mmole) was added. The reaction mixture was stirred for 1 hour at rt. Thereaction was monitored by TLC and showed the complete disappearance of startingmaterial. The resultant white mixture was filtered to remove 1, 3dicyclohexyleurea. Filtrate was concentrated and purified by columnchromatography using DCM/MeOH (98.5:1.5) as eluent to obtain compound 16 as a white solid. (2.1 g, 91%). [alpha]21D = 26 (c 0.1, CHCl3). 1HNMR: (CDCl3, 400 MHz) 1.38 (s, 9H), 2.20 (t, 1H, J = 2.44 Hz), 2.69 (dd, 1H, J = 4.36 Hz, J = 15.8 Hz), 2.86 (dd, 1H, J= 4.72 Hz, J = 15.84 Hz), 3.69 (s,3H), 3.95-3.97 (m, 2H), 4.47-4.49 (m, 1H), 5.76-5.78 (d, 1H, J = 8.4 Hz), 6.76 (t, 1H, J = 4.68 Hz). 13C NMR: (CDCl3,100 MHz) 28.3, 29.1, 37.6, 50.3, 52.7,71.6, 79.4, 80.0, 155.7, 169.8, 172.01. IR (KBr) 3301, 2979, 1709, 1660, 1528, 1438, 1393, 1368, 1347, 1251, 1166,1056, 1029, 861, 762, 661 cm-1. HRMS (ESI): m/z calcd. for C13H21N2O5[M+H]+ 285.1445; found 285.1450.
  • 17
  • [ 10165-86-3 ]
  • [ 2450-71-7 ]
  • C19H19N3O4 [ No CAS ]
  • 18
  • [ 186534-02-1 ]
  • [ 2450-71-7 ]
  • C11H15N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In a 50 mL round-bottom flask freshly prepared TMP-CHO (150 mg 1 mmol) was added and dissolved in 20 mL of 1 2-dichloroethane propargylamine (66 mg 1.2 mmol) was added slowly at room temperature the reaction was run at at room temperature for 2 hours triacetoxy sodium borohydride (424 mg 2 mmol) was added and monitored by TLC about 2 hours later the reaction was complete 10 mL of 10 K2CO3was added for quenching. The resulting material was extracted with dichloromethane dried over anhydrous sodium sulfate filtered and concentrated and purified with silica gel column chromatography (ethyl acetatepetroleum ether 32) to give the compound MT-012 as a yellow solid (163mg 86) . ESI-MS [M+H]+m/z 190.3.1H-NMR (CDCl3) 3.96 (s 2H) 3.56 (d J2.4 Hz 2H) 2.51 (s 3H) 2.49 (s 6H) 2.26 (t J2.4 Hz 1H) .
86% In 1,2-dichloro-ethane; at 20℃; for 2h; 10110] In a 50 mE round-bottom flask, freshly prepared TMP-CHO(lSOmg, 1 mmol)was addedanddissolvedin20 mE of 1 ,2-dichloroethane, propargylamine (66 mg, 1.2 mmol) was added slowly at room temperature, the reaction was run at room temperature for 2 hours, triacetoxy sodium borohydride (424 mg, 2 mmol) was added and monitored by TEC, about 2 hours later the reaction was complete, 10 mE of 10% K2C03 was added for quenching. The resulting material was extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered and concentrated, and purified with silica gel colunm chromatography (ethyl acetate:petroleum ether 3:2) to give the compound MT-012 as a yellow solid (163 mg, 86%). ESI-MS: [M+H] mlz 190.3. ?H-NMR (CDC13): 3.96 (s, 2H); 3.56 (d, J=2.4 Hz, 2H); 2.51 (s, 3H); 2.49 (s, 6H); 2.26 (t, J=2.4 Hz, 1H).
  • 19
  • [ 5926-51-2 ]
  • [ 2450-71-7 ]
  • 3-bromo-1-(prop-2-yn-1-yl)-1H-pyrrole-2,5-dione [ No CAS ]
  • 20
  • [ 3471-31-6 ]
  • [ 2450-71-7 ]
  • N-propargyl-2-(5-methoxy-1H-indol-3-yl)acetamide [ No CAS ]
  • 21
  • [ 97-08-5 ]
  • [ 2450-71-7 ]
  • C9H7ClN2O4S [ No CAS ]
  • 22
  • [ 1180-71-8 ]
  • [ 2450-71-7 ]
  • 2-((1S,3aS,4aR,4bR,9aR,11aS)-1-(furan-3-yl)-9a-(hydroxymethyl)-4b,7,7,11a-tetramethyl-3,5-dioxotetradecahydroisobenzofuro[5,4-f]oxireno[2,3-d]isochromen-9-yl)-N-(prop-2-yn-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With montmorillonite K-10; In ethanol; at 80℃; for 0.5h;Sealed tube; Microwave irradiation; General procedure: To a solution of 1 (2.0 mmol) in absolute EtOH (8.0 mL)in a glass tube was added dropwise the appropriate amine(3.6 mmol) and K-10 (0.3 g mmol-1); the quartz tubewas sealed with reaction mixture and introduced intoa microwave oven. The flask was irradiated for 30 min(150 W) the temperature of 80 C. After completion of thereaction the mixture was filtered, the organic phase wasdried with Na2SO4, filtered and the solvent was evaporatedunder reduced pressure to give the crude products. All thecompounds were purified by column chromatographyon silica gel using 2-5% EtOH-CH2Cl2 as eluent to giveanalytically pure products 3a-m. The products werecharacterized by corresponding spectroscopic data (1H and13C NMR, and HRMS).
  • 23
  • [ 2450-71-7 ]
  • [ 72040-64-3 ]
  • [ 940932-24-1 ]
  • 24
  • [ 1189513-51-6 ]
  • [ 2450-71-7 ]
  • 5-bromo-3-chloro-N-(prop-2-yn-1-yl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% To a stirred solution of <strong>[1189513-51-6]5-bromo-3-chloropicolinic acid</strong> (10 g, 42.3 mmol) in DMF (100 mL) was added HOBT (3.24 g, 21.15 mmol), EDCI (6.57 g, 42.3 mmol) and Et3N (11.79 mL, 85 mmol) and the reaction mixture was allowed to stir for 30 min. Thereafter prop-2-yn-1-amine (3.30 mL, 51.6 mmol) was added and reaction mixture was allowed to stir for 14 h at 25eC. Upon completion, reaction mixture was quenched with water (500 mL) and aqueous phase was extracted with ethyl acetate (200 mL x 3), combined organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was rotary evaporated and residue was purified by flash column chromatography (silica gel) to afford 3.50 g (30percent) of the titled product as a white solid. 1HNMR (400 MHz, DMSO-d6) U9.12 (t, J = 6.0 Hz, 1H), 8.73 (s, 1H), 8.48 (s, 1H), 4.12 ' 3.98 (m, 2H), 3.17 (s, 1H). ESI-MS (m/z) 274.9 (MH)\
  • 25
  • [ 590-28-3 ]
  • [ 2450-71-7 ]
  • [ 5221-62-5 ]
YieldReaction ConditionsOperation in experiment
To a solution of propargylamine (3.2 mL, 50 mmol) in aqueous HC1 soulution (1.0 N, 50 mL) was added KOCN (16 g, 200 mmol) at r.t. After stirring overnight at 60 C, the mixture was cooled to 0 C to give a white precipitate. After filtration, the solid was dissolved in MeOH (150 ml) and stirred with silica gel (25 g) for 6 h. The mixture was then filtered and concentrated under vacuum to give the desired urea 4a as a white solid (3.5 g, 71%) without further purification. NMR (400 MHz, MeOD) delta 3.88 (d, J = 2.5 Hz, 2H), 2.54 (t, J = 2.5 Hz, 1H). 13C NMR (126 MHz, MeOD) delta 161.55, 81.63, 71.80, 30.18. m/z HRMS (ESI) found [M+H]+ 99.0552, C4HvN20+ requires 99.0553.
  • 26
  • [ 80286-58-4 ]
  • [ 2450-71-7 ]
  • 2-((1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)-N-(prop-2-yn-1-yl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% 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 25℃; for 6h;Inert atmosphere; To a solution of <strong>[80286-58-4]artemisinic acid</strong> (1), (100 mg, 1 equiv), HATH (191 mg, 1.2 equiv) and DIPEA (87 pL, 1.2 equiv) in DMF (10 mL) was added propargyl amine (32 pL, 1.2 equiv) at 25 C under a argon atmosphere. The mixture was stirred for 6 h. After completion of reaction (TLC), the solvent was removed in vacuo and the resulting oil residue was diluted with DCM (15 mL) and extracted with water. The combined DCM layers were dried over Na2S04 filtered and concentrated. The crude product was purified by flash chromatography to give compound 3 (109 mg) in 95% yield. 1H NMR (500 MHz, CDCl3) d = 6.29 (brs, 1H), 5.63 (s, 1H), 5.15 (s, 1H), 4.96 (s, 1H), 4.16 - 4.11 (m, 1H), 4.03 - 3.98 (m, 1H), 2.74 (d, J= 12.6 Hz, 1H), 2.42 (s, 1H), 2.23 (t, 7= 2.7 Hz, 1H), 2.15 (s, 1H), 1.90 - 1.85 (m, 2H), 1.75 - 1.66 (m, 2H), 1.57 (s, 3H), 1.56 -1.49 (m, 1H), 1.44 - 1.37 (m, 3 H), 1.29 - 1.23 (m, 1H), 0.86 (d, J = 5.3 Hz, 3H). 13C NMR (125 MHz, CDCl3) d = 169.5, 148.7, 135.1, 120.2, 116.6, 79.6, 71.6, 42.6, 41.2, 37.7, 35.0, 29.4, 27.5, 26.4, 25.4, 25.3, 23.7, 19.7. HRMS (ESI): m/z calcd for [M+H]+, CI8H26ON 272.2009 found 272.2004
  • 27
  • [ 34231-77-1 ]
  • [ 2450-71-7 ]
  • N-prop-2-ynylpyridazine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 100℃; for 4h;Microwave irradiation; To a solution of <strong>[34231-77-1]methyl pyridazine-4-carboxylate</strong> (1 g) in methanol (2.5 ml_) was added prop-2-yn-1- amine (4 g) and the mixture was heated at 100C under microwave irradiation for 4 hours. After cooling to room temperature, the reaction mixture was concentrated and purified by silica gel chromatography eluting with 90-100% ethyl acetate in cyclohexane to afford A/-prop-2-ynylpyridazine- 4-carboxamide as white solid. (0804) NMR (400MHz, DMSO-de) 9.53-9.56 (m, 1 H) 9.47-9.52 (m, 1 H) 9.42-9.46 (m, 1 H) 7.96-8.03 (m, 1 H) 4.06-4.16 (m, 2H) 3.19-3.26 (m, 1 H)
  • 28
  • [ 22514-58-5 ]
  • [ 2450-71-7 ]
  • 2-bromo-N-(prop-2-yn-1-yl)benzo[d]thiazole-6-carboxamide [ No CAS ]
  • 29
  • [ 50461-74-0 ]
  • [ 2450-71-7 ]
  • ethyl 2-hydroxy-n-valerate [ No CAS ]
  • ethyl (R)-2-(propargylamino)valerate [ No CAS ]
  • ethyl (S)-2-(propargylamino)valerate [ No CAS ]
  • 30
  • [ 50461-74-0 ]
  • [ 2450-71-7 ]
  • ethyl 2-hydroxy-n-valerate [ No CAS ]
  • ethyl (R)-2-(propargylamino)valerate [ No CAS ]
  • 31
  • [ 50461-74-0 ]
  • [ 2450-71-7 ]
  • ethyl (S)-2-(propargylamino)valerate [ No CAS ]
  • 32
  • [ 17115-51-4 ]
  • [ 2450-71-7 ]
  • 2,3-dihydrothieno[3,2-b]pyridine 1,1-dioxide [ No CAS ]
  • 33
  • [ 16303-60-9 ]
  • [ 2450-71-7 ]
  • C12H9NO2 [ No CAS ]
 

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