Select Region or Location
Americas
  • Argentina
  • Brazil
  • Canada
  • Mexico
  • United States
  • Other Americas
Europe
  • Austria
  • Belgium
  • Bulgaria
  • Croatia/Hrvatska
  • Cyprus
  • Czech Republic
  • Denmark
  • Estonia
  • Finland
  • France
  • Germany
  • Greece
  • Hungary
  • Ireland
  • Italy
  • Latvia
  • Liechtenstein
  • Lithuania
  • Luxembourg
  • Malta
  • Netherlands
  • Norway
  • Poland
  • Portugal
  • Romania
  • Slovak Republic
  • Slovenia
  • Spain
  • Sweden
  • Switzerland
  • Turkey
  • United Kingdom
  • Other Europe
Asia Pacific
  • Australia
  • China
  • India
  • Indonesia
  • Japan
  • Korea, Republic of
  • Malaysia
  • New Zealand
  • Philippines
  • Singapore
  • Thailand
  • Vietnam
  • Other Asia Pacific
Africa And Middle East
  • Egypt
  • Israel
  • Other Africa And Middle East
USD
Home Cart Sign in  
Chemical Structure| 1255942-06-3 Chemical Structure| 1255942-06-3

Structure of DBCO-amine
CAS No.: 1255942-06-3

Chemical Structure| 1255942-06-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}
    {[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1255942-06-3 ]

CAS No. :1255942-06-3
Formula : C18H16N2O
M.W : 276.33
SMILES Code : O=C(N1C2=CC=CC=C2C#CC3=CC=CC=C3C1)CCN
English Name :3-Amino-1-(11,12-didehydrodibenz[b,f]azocin-5(6H)-yl)-1-propanone
MDL No. :MFCD22380759
InChI Key :OCCYFTDHSHTFER-UHFFFAOYSA-N
Pubchem ID :77078258

Safety of [ 1255942-06-3 ]

Application In Synthesis of [ 1255942-06-3 ]

* 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 [ 1255942-06-3 ]

[ 1255942-06-3 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 1255942-06-3 ]
  • [ 1255942-08-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C 1.2: 4 h / 20 °C 2.1: trifluoroacetic acid / tetrahydrofuran / 20 °C
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 25 °C / Inert atmosphere 1.2: 2 h / 25 °C 2.1: piperidine / N,N-dimethyl-formamide / 2 h / 25 °C / Inert atmosphere
  • 2
  • [ 1337920-23-6 ]
  • [ 1255942-06-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In methanol; water at 20℃;
90.6 % With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; 1.1.8 (8) Preparation of compound 11 Compound 10 (1.2g, 0.0032mol) was added to THF (25ml), 5ml of potassium carbonate (0.66g, 0.0048mol) aqueous solution was added dropwise at 0°C, overnight at room temperature, water was added to quench the reaction, extracted with EA, and dried to obtain 0.8g of compound 11 with a yield of 90.6%.Compound 11 was named DBCO-NH2.
  • 3
  • [ 23112-88-1 ]
  • [ 1255942-06-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: lithium aluminium tetrahydride / diethyl ether / 15 h / Reflux 2: pyridine / dichloromethane / 0.5 h / 20 °C 3: pyridinium perbromide hydrobromide / dichloromethane / 20 °C 4: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C 5: potassium carbonate / methanol; water / 20 °C
  • 4
  • [ 1255942-06-3 ]
  • [ 25357-95-3 ]
  • [ 1528700-78-8 ]
YieldReaction ConditionsOperation in experiment
48.1% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 24h; 9 Compound 1 : CTA DBCO Bridging molecule 1,3,5-Cyclohexanetricarboxylic acid (3.47 mg, 16.08 μηιοεβ), l-ethyl-3-(3'- dimethylaminopropyl)carbodiimide hydrochloride (14.1 mg, 73.55 μηιοεβ) and hydroxybenzotriazole hydrate (11 mg, 71.89 μιηοεβ) were added to a 140 μ solution of Ν,Ν-dimethylformamide (DMF). It was shaken until everything was dissolved. To this added DBCO amine (20.2 mg, 73.1 μιηοεβ) and shaken for 24 hours. The desired product was purified by reversed phase HPLC (flow rate 2 mL/min, runtime 40 minutes), solvent A (0.1% trifluoroacetic acid (TFA) in water), solvent B (0.1% TFA in acetonitrile (ACN)), gradient 0% B to 100% B over 30 minutes, isocratic 100% B for next 10 minutes, C 18 column with TMS endcapping (5 μιη, 250 χ 10 mm, Phenomenex): the crude reaction mixture was run multiple times and the fractions(or peak) at 34-35 minutes were collected, combined, dried and analyzed using HPLC and mass spectrometry. Yield 7.6 mg (48.1% yield), Purity (95%, HPLC). TLC (EtOAc/MeOH, 50:50 v/v): Rf = 0.82; UV/vis (methanol) (ελ): 310 nm (36000 M-l cm-1), reversed phase HPLC (flow rate 1 mL/min, runtime 30 minutes), solvent A (0.1% TFA in water), solvent B (0.1% TFA in ACN), gradient 0% B to 100% B over 25 minutes, isocratic 100% B for 5 minutes, CI 8 with Hypersil column (5 μηι, 250 χ 4.6 mm, Agilent Microsorb): retention time (min) 21.41, ESI-MS {mlz): [MH]+ calculated for 991.4; found, 991.3. See FIG. 12D for HPLC and MS.
  • 5
  • [ 1255942-06-3 ]
  • [ 35013-72-0 ]
  • [ 1418217-95-4 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In N,N-dimethyl-formamide for 7h;
49% With triethylamine In N,N-dimethyl-formamide for 3h; 5 Example 5. Synthesis of DIBAC-biotin 30 (Schematically depicted in Figure 8) To a solution of amine 29, commercially available from ClickChemistryTools (50 mg, 0.18 mmol) in DMF (2 mL) was added biotin-OSu (62 mg, 0.18 mmol) and Et3N (50 μΕ, 0.36 mmol). The reaction mixture was stirred for 3 h followed by concentration under reduced pressure. Flash column chromatography (DCM:MeOH 99: 1-90: 10) afforded DIBAC-biotin 30 (44 mg, 0.09 mmol, 49%). 1H-NMR (300 MHz, CDC13): δ 7.66-7.62 (m, 1H), 7.40-7.24 (m, 7H), 6.67-6.60 (m, 1H), 6.53-6.49 (m, 1H), 5.75 (d, J = 8.8 Hz, 1H), 5.13 (dd, J = 2.9, 14.0 Hz, 1H), 4.47-4.43 (m, 1H), 4.29-4.28 (m, 1H), 3.68 (d, J = 13.9 Hz, 1H), 3.34-3.30 (m, 1H), 3.17-3.08 (m, 2H), 2.92-2.67 (m, 3H), 2.50-2.42 (m, 1H), 2.10-1.95 (m, 2H), 1.73-1.24 (m, 6H). LRMS (ESI+) calcd for C28H30N4O3S ( +H+) 503.2, found 503.1.
  • 6
  • [ 108-55-4 ]
  • [ 74124-79-1 ]
  • [ 1255942-06-3 ]
  • [ 1269997-07-0 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: glutaric anhydride,; DBCO-amine With triethylamine In dichloromethane at 20℃; for 2h; Stage #2: di(succinimido) carbonate In dichloromethane at 20℃; for 2h; 9.7 Example 9-7. Synthesis of DIBAC-vc-PABA-MMAF 41 (Schematically depicted in Scheme 11) DIBAC-amine 29, commercially available from ClickChemistryTools (430 mg, 1.50 mmol) was dissolved in DCM (15 mL) and treated with glutaric acid anhydride (213 mg, 1.87 mmol) and Et3N (647 μ., 4.67 mmol)_at rt. The reaction was stirred for 2h, followed by the addition of DSC (478 mg, 1.87 mmol). After another 2 h of stirring at rt, DCM (30 mL) was added and the reaction was washed with H20 (3 x 20 mL). The organic phase was dried over Na2S04and the solvent removed under reduced pressure. Flash chromatography (0: 100-2:98 EtOAc:MeOH) afforded the DIBAC-OSu ester (368 mg, 0.75 mmol, 48%).Next, to a solution of the DIBAC-OSu ester (1 mg, 0.003 mmol) in DMF (0.2 mL) was added vc-PABA-MMAF (2 mg, 0.002 mmol) and triethylamine (1 μ, 0.007 mmol). The solution was stirred overnight followed by concentration. Purification with HPLC (reversed phase, MeCN:H20 + 0.1% TFA) gave 41 (0.9 mg, 0.0006 mmol, 33%). LCMS analysis gave one peak with mass 1510.40 (expected for C8iHn3Ni20i6 = 1510.83).
  • 7
  • [ 1255942-06-3 ]
  • [ 108-24-7 ]
  • [ 1645270-69-4 ]
YieldReaction ConditionsOperation in experiment
92% With dmap; triethylamine In dichloromethane at 20℃; for 16h; 13 Example 13. Synthesis of compound 26b To a solution of DIBAC-NH2 26a (100 mg, 0.362 mmol) in DCM (5 mL) was added Ac20 (51 μ, 0.543 mmol), NEt3 (101 μ, 0.724 mmol) and a cat. amount of DMAP. After stirring for 16 h at rt water (5 mL) was added and the mixture was extracted with DCM (3 x 10 mL). The organic layer was dried (Na2S04), filtered and concentrated in vacuo. The residue was purified by column chromatography (MeOH/DCM, 1 : 19) to afford 26b (106 mg, 92%) as a white solid. Rf 0.32 (MeOH/DCM, 1 : 19). 1H NMR (CDC13, 400 MHz): δ 7.68 (d, J = 7.5 Hz, 1H), 7.42-7.26 (m, 7H), 6.07-6.02 (m, 1H), 5.14 (d, J = 13.9 Hz, 1H), 3.70 (d, J = 13.9 Hz, 1H), 3.38-3.30 (m, 1H), 3.24-3.16 (m, 1H), 2.46 (ddd, J= 16.6, 7.7, 4.0 Hz, 1H), 1.96 (ddd, J= 16.6, 7.3, 3.7 Hz, 1H), 1.81 (s, 3H) ppm. 13C NMR (CDC13, 125 MHz): δ 172.5, 170.0, 151.2, 148.1, 132.2, 129.2, 128.7, 128.6, 128.5, 128.0, 127.4, 125.7, 123.1, 122.7, 114.9, 107.9, 55.7, 35.4, 34.9, 23.3. HRMS (ESI+) m/z calcd for C20Hi8N2NaO2 (M + Na)+: 341.1266, found: 341.1275.
92% With dmap; triethylamine In dichloromethane at 20℃; for 16h; 13 Synthesis of Compound 26b To a solution of DIBAC-NH2 26a (100 mg, 0.362 mmol) in DCM (5 mL) was added Ac2O (51 μL, 0.543 mmol), NEt3 (101 μL, 0.724 mmol) and a cat. amount of DMAP. After stirring for 16 h at rt water (5 mL) was added and the mixture was extracted with DCM (3×10 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (MeOH/DCM, 1:19) to afford 26b (106 mg, 92%) as a white solid. Rf 0.32 (MeOH/DCM, 1:19). 1H NMR (CDCl3, 400 MHz): δ 7.68 (d, J=7.5 Hz, 1H), 7.42-7.26 (m, 7H), 6.07-6.02 (m, 1H), 5.14 (d, J=13.9 Hz, 1H), 3.70 (d, J=13.9 Hz, 1H), 3.38-3.30 (m, 1H), 3.24-3.16 (m, 1H), 2.46 (ddd, J=16.6, 7.7, 4.0 Hz, 1H), 1.96 (ddd, J=16.6, 7.3, 3.7 Hz, 1H), 1.81 (s, 3H) ppm. 13C NMR (CDCl3, 125 MHz): δ 172.5, 170.0, 151.2, 148.1, 132.2, 129.2, 128.7, 128.6, 128.5, 128.0, 127.4, 125.7, 123.1, 122.7, 114.9, 107.9, 55.7, 35.4, 34.9, 23.3. HRMS (ESI+) m/z calcd for C20H18N2NaO2 (M+Na)+: 341.1266. found: 341.1275.
90% With dmap; triethylamine In dichloromethane; water at 20℃; for 16h; Synthesis of N-(3-N'-acetyl-3-aminopropanoyl)-dibenzoazacyclooctyne (DIBAC-NHAc) (14): Synthesis of N-(3-N'-acetyl-3-aminopropanoyl)-dibenzoazacyclooctyne (DIBAC-NHAc) (14): To a solution of DIBAC-NH2 (80% purity, 90 mg, 0.33 mmol) in DCM (5 mL) was added Ac2O (46 μL, 0.49 mmol, 1.5 eq.), TEA (91 μL, 0.652 mmol, 2 eq.) and a cat. amount of 4-dimethylaminopyridine (DMAP). After stirring for 16 h at rt water (5 mL) was added and the mixture was extracted with DCM (3 * 10 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (MeOH/DCM, 1:19) to afford 14 (93 mg, 90%) as a white solid. RF 0.32 (MeOH/DCM, 1/19). 1H NMR (CDCl3, 400 MHz): δ 7.68 (d, J = 7.5 Hz, 1H), 7.42-7.26 (m, 7H), 6.07-6.02 (m, 1H), 5.14 (d, J = 13.9 Hz, 1H), 3.70 (d, J = 13.9 Hz, 1H), 3.38-3.30 (m, 1H), 3.24-3.16 (m, 1H), 2.46 (ddd, J = 16.6, 7.7, 4.0 Hz, 1H), 1.96 (ddd, J = 16.6, 7.3, 3.7 Hz, 1H), 1.81 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ 172.5, 170.0, 151.2, 148.1, 132.2, 129.2, 128.7, 128.6, 128.5, 128.0, 127.4, 125.7, 123.1, 122.7, 114.9, 107.9, 55.7, 35.4, 34.9, 23.3. HRMS (ESI) m/z for C20H18N2NaO2: (M + Na+), calcd: 341.1266, found: 341.1275.
  • 8
  • [ 1255942-06-3 ]
  • [ 1787252-03-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / chloroform / 0.5 h / 20 °C 1.2: 20 °C 2.1: dicyclohexyl-carbodiimide / chloroform / 20 °C
  • 9
  • [ 108-55-4 ]
  • [ 1255942-06-3 ]
  • [ 1337920-25-8 ]
YieldReaction ConditionsOperation in experiment
45% In dichloromethane at 20℃; for 2h; Compound 84: 5-[[3-(1 1,1 2-didehydrodibenz[b,f]azocin-5(6H)-yI)-3-oxopropyl]amino]-5-oxopentanoic acid To a solution of DBCO-amine (50 mg, 180.9 pmol) in DCM (2 mL) was added glutaricanhydride (21.1 mg, 180.9 pmol). The reaction medium was stirred for 2 h at RT,concentrated in vacuo and purified by flash chromatography on 4 g of silica gel(gradient elution DCM/MeOH) to give 32.6 mg of compound 84 (45%).RMN 1H (400 MHz, ö in ppm, DMSO-d6): 1.59 (m, 2 H) ; 1.81 (m, 1 H); 1.94 (t, J =7.4 Hz, 2 H); 2.11 (t, J = 7.4 Hz, 2 H); 2.40 (m, 1 H); 2.91 (m, 1 H); 3.09 (m, 1 H);3.62 (d, J = 14.2 Hz, 1 H); 5.13 (d, J = 14.2 Hz, 1 H); 7.38 to 7.53 (m, 6 H); 7.56 to7.67 (m, 3 H); 12.05 (broad m, 1 H).
86 % In dichloromethane at 20℃; Compound 4: 5-[[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexaen- 10-yn-2-yl)-3-oxo-propyl]amino]-5-oxo-pentanoic acid To a solution of dibenzocyclooctyne-amine ([1255942-06-3], 77.5 mg, 280 µmol) in anhydrous DCM (2 mL) was added glutaric anhydride (42.5 mg, 364 µmol). The colorless reaction mixture was stirred overnight at RT and purified by flash chromatography on 5 g of silica gel (gradient elution EtOAc to EtOAc/MeOH/ H2O 7:2:1) to give 94 mg of compound 4 as a white foam (86%). NMR1H (400 MHz, δ in ppm, DMSO-d6): 1.59 (quin, J = 7 Hz, 2 H); 1.83 (ddd, J = 6, 8 and 16 Hz, 1 H); 1.94 (t, J = 8 Hz, 2 H); 2.11 (t, J = 7 Hz, 2 H); 2.40 (ddd, J = 6, 8 and 16Hz, 1 H); 2.87 (m, 1 H); 3.09 (m, 1 H); 3.63 (d, J = 14 Hz, 1 H); 5.04 (d, J = 14 Hz, 1 H); 7.26 to 7.42 (m, 3 H); 7.43 to 7.52 (m, 3 H); 7.54 to 7.67 (m, 3 H); 12.01 (large s, 1 H).
86 % In dichloromethane at 20℃; Compound 4: 5-[[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexaen- 10-yn-2-yl)-3-oxo-propyl]amino]-5-oxo-pentanoic acid To a solution of dibenzocyclooctyne-amine ([1255942-06-3], 77.5 mg, 280 µmol) in anhydrous DCM (2 mL) was added glutaric anhydride (42.5 mg, 364 µmol). The colorless reaction mixture was stirred overnight at RT and purified by flash chromatography on 5 g of silica gel (gradient elution EtOAc to EtOAc/MeOH/ H2O 7:2:1) to give 94 mg of compound 4 as a white foam (86%). NMR1H (400 MHz, δ in ppm, DMSO-d6): 1.59 (quin, J = 7 Hz, 2 H); 1.83 (ddd, J = 6, 8 and 16 Hz, 1 H); 1.94 (t, J = 8 Hz, 2 H); 2.11 (t, J = 7 Hz, 2 H); 2.40 (ddd, J = 6, 8 and 16Hz, 1 H); 2.87 (m, 1 H); 3.09 (m, 1 H); 3.63 (d, J = 14 Hz, 1 H); 5.04 (d, J = 14 Hz, 1 H); 7.26 to 7.42 (m, 3 H); 7.43 to 7.52 (m, 3 H); 7.54 to 7.67 (m, 3 H); 12.01 (large s, 1 H).
  • 10
  • [ 1255942-06-3 ]
  • [ 1426090-03-0 ]
  • [ 2259859-41-9 ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: 4-carboxy-2-(7-(dimethylamino)-3-(dimethyliminio)-5,5-dimethyl-3,5-dihydrodibenzo[b,e]silin-10-yl)benzoate 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 1h; Inert atmosphere; Stage #2: N-(3-aminopropionyl)-5,6-dihydro-11,12-didehydrodibenzo[b,f]azocine In N,N-dimethyl-formamide for 2h; Inert atmosphere;
  • 12
  • [ 1255942-06-3 ]
  • [ 58-85-5 ]
  • [ 1418217-95-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: biotin With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trimethylamine In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: N-(3-aminopropionyl)-5,6-dihydro-11,12-didehydrodibenzo[b,f]azocine In dimethyl sulfoxide at 20℃;
  • 13
  • [ 1255942-06-3 ]
  • [ 2375193-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C 2: sodium hydroxide; water / tetrahydrofuran / 0 - 20 °C
  • 14
  • [ 1255942-06-3 ]
  • [ 2567570-42-5 ]
  • [ 1807512-43-1 ]
YieldReaction ConditionsOperation in experiment
67% In methanol at 20℃; 3 2. Synthesis of compound 3 5,5-Dimethyl-1,3-cyclohexanedione (1.06 g, 7.57 mmol) was slowly added to compound 2 (3.72 g, 7.57 mmol) and EDCI (1.14 g, 5.96 mmol) in DMF at room temperature (30 ml) was removed from the solution, DMAP (93 mg, 0.76 mmol) was added and left at room temperature overnight. TLC showed the reaction was complete. The reaction solution was spin-dried DMF, added with 20 ml of saturated brine, adjusted to acidity with hydrochloric acid, extracted with dichloromethane, washed three times with water, and pulled through the column to obtain 2.23 g of white solid with a yield of 48%.
 

Historical Records

Categories

Similar Product of
[ 1255942-06-3 ]

Chemical Structure| 2007915-94-6

A503794 [2007915-94-6]

Dbco-amine TFA

Reason: Free-salt