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[ CAS No. 105-83-9 ] {[proInfo.proName]}

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Chemical Structure| 105-83-9
Chemical Structure| 105-83-9
Structure of 105-83-9 * Storage: {[proInfo.prStorage]}
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Li, Bowen ; Manan, Rajith Singh ; Liang, Shun-Qing , et al. DOI: PubMed ID:

Abstract: The expanding applications of nonviral genomic medicines in the lung remain restricted by delivery challenges. Here, leveraging a high-throughput platform, we synthesize and screen a combinatorial library of biodegradable ionizable lipids to build inhalable delivery vehicles for mRNA and CRISPR-Cas9 gene editors. Lead lipid nanoparticles are amenable for repeated intratracheal dosing and could achieve efficient gene editing in lung epithelium, providing avenues for gene therapy of congenital lung diseases.

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Product Details of [ 105-83-9 ]

CAS No. :105-83-9 MDL No. :MFCD00008217
Formula : C7H19N3 Boiling Point : -
Linear Structure Formula :(NH2C3H6)2NCH3 InChI Key :KMBPCQSCMCEPMU-UHFFFAOYSA-N
M.W : 145.25 Pubchem ID :7777
Synonyms :

Safety of [ 105-83-9 ]

Signal Word:Danger Class:6.1,8
Precautionary Statements:P501-P260-P270-P262-P271-P264-P280-P284-P303+P361+P353-P301+P330+P331-P362-P301+P312+P330-P302+P350+P310-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405 UN#:2927
Hazard Statements:H310+H330-H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 105-83-9 ]

* 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 [ 105-83-9 ]

[ 105-83-9 ] Synthesis Path-Downstream   1~97

  • 1
  • [ 50-00-0 ]
  • [ 105-83-9 ]
  • [ 3855-32-1 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogen; In methanol; water; at 90℃; under 22502.3 Torr;Autoclave; Green chemistry; Compound 4 (14.5 g, 0.1 mol), methanol (150 mL), aqueous formaldehyde solution (40.6 g, 0.5 mol, 37 wt%) and W-3 Raney Ni (3 g) were added to the autoclave. The air in the autoclave was replaced with nitrogen (3 times) and then with hydrogen (3 times). The dangers of hydrogen/oxygen contact with the catalyst should always be given attention since a mixture of hydrogen and oxygen is capable to of leading to an explosion. Then the reaction mixture was stirred ata rotation speed of 500 rpm at 90 C, 3.0 MPa. The reaction was not stopped until the hydrogen pressure no longer dropped over 5 h and then the mixture was filtered. When the mixture was filtered, Raney Ni should always be kept wet with ethanol and should never directly have contact with the air since dry Raney Ni can easily burst into flames in the air which could result in significant hazards. After the filtration, volatiles were evaporated to give PMDPTA: viscous, yellow liquid; 16.28 g, 81.0 % yield; 1H NMR (CDCl3, 400 MHz) delta: 1.63 (m, J = 7.6Hz, 4H, CH2), 2.21 (s, 15H, CH3), 2.27 (t, J = 7.4 Hz, 4H, CH2), 2.35 (t, J = 7.4 Hz, 4H, CH2); 13C NMR (CD3OD, 151 MHz) delta: 57.3 (2 ×C, CH2), 55.2 (2 × C, CH2), 44.1 (4 × C, CH3), 40.9 (1 × C, CH3), 24.2 (2 × C, CH2); ESI-HRMS m/z [M + H]+: calcd 202.2239, observed 202.2287.
  • 2
  • [ 1555-58-4 ]
  • [ 105-83-9 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogen; sodium hydroxide; In ethanol; at 90℃; under 15001.5 Torr;Autoclave; Green chemistry; Compound 3 (30 mL), ethanol (150 mL), sodium hydroxide (0.18 g) and W-3 Raney Ni (6 g) were added into the 300 mL autoclave. The air in the autoclave was replaced with nitrogen by 3 times and then with hydrogen by 3 times. The dangers of hydrogen/oxygen contact with the catalyst should always be given attention since a mixture of hydrogen and oxygen is capable of leading to an explosion. After the reaction mixture was stirred at 90 C, 2.0 MPa, the reaction was not stopped until the hydrogen pressure no longer dropped over 6 h and then the mixture was filtered. When the mixture was filtered, Raney Ni should always be kept wet with ethanol and should never have direct contact with air since dry Raney Ni can easily burst into flames in the air, which could result in significant hazards. After the filtration, the solvent was evaporated to give 4: viscous, colourless liquid; 25.5 g, 85.0% yield; 1H NMR (CDCl3, 400 MHz) delta: 1.65 (m, J = 7.6 Hz, 4H,CH2), 2.26 (s, 3H, CH3), 2.37 (t, J = 7.4, 4H, CH2), 2.48 (t, J = 7.4 Hz,4H, CH2), 5.15 (s, 4H, NH2).
  • 3
  • [ 105-83-9 ]
  • [ 37942-07-7 ]
  • N,N′-bis(3,5-di-tert-butyl-2-hydroxybenzyliden)-1,7-diamino-4-methyl-4-azaheptane [ No CAS ]
  • 5
  • [ 60117-35-3 ]
  • [ 105-83-9 ]
  • N-methyl-N-<3-(5-azido-2-nitrobenzoylamino)propyl>propylene-1,3-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane for 1.5h;
  • 6
  • [ 105-83-9 ]
  • [ 4053-08-1 ]
  • 2-(3-((3-aminopropyl)(methyl)amino)propyl)-6-chloro-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In ethanol Reflux; 2.1.1 General procedure for the preparation of compounds L1-L14 General procedure: To a solution of 4-substituted-1,8-naphthalic anhydride (1.0 mmol) in ethanol (30 mL) was added various alkylamine (3.0 mmol). The reaction mixture was heated under reflux for 20-60 min, and cooled down to room temperature. The solution was concentrated in rotary evaporator and washed with diethyl ether, to give crude yellow solids L1-L14. The residue was purified by using chromatograph on silica gel with DCM/MeOH (50/1-30/1) to give desire compounds.
37% In ethanol for 15h; Ambient temperature;
  • 7
  • [ 21814-48-2 ]
  • [ 105-83-9 ]
  • 1,1'-<(methylimino)bis(3,1-propanediylimino)>bis<7-methoxy-4-nitro-9(10H)-acridinone> [ No CAS ]
  • 8
  • [ 105-83-9 ]
  • [ 99009-49-1 ]
  • 1,1'-<(methylimino)bis(3,1-propanediylimino)>bis<7-hydroxy-4-nitro-9(10H)-acridinone> [ No CAS ]
  • 9
  • [ 105-83-9 ]
  • [ 166756-49-6 ]
  • [ 166756-69-0 ]
  • 10
  • [ 105-83-9 ]
  • [ 20621-51-6 ]
  • 1,1'-<(methylimino)bis(3,1-propanediylimino)>bis<4-nitro-9(10H)-acridinone> [ No CAS ]
  • 12
  • [ 105-83-9 ]
  • [ 24424-99-5 ]
  • [ 87530-14-1 ]
YieldReaction ConditionsOperation in experiment
96% In tetrahydrofuran; The synthesis of the receptors 1 and 2 (scheme 1) started with the coupling of two equivalents of the mono-BOC-protected N-methyl-N,N-di(3-aminopropyl)amine 6 with the diacid chlorides of either fumaric acid (for 1) or maleic acid (for 2). The synthesis of the mono-BOC-protected species was straightforward and the excess of amine starting material was recovered from aqueous waste by drying and distillation. The resulting intermediates (9 and 10) were subsequently deprotected using gaseous HCl and isolated as hydrochloride salts after purification by preparative gel permeation chromatography (Sephadex G-10, eluent water). The degree of protonation was established by potentiometric titrations, vide infra.
27% In tetrahydrofuran; at 0 - 20℃; for 20h; To a stirred solution of 3,3?-diamino-N-methyldipropylamine (22.0 g, 151.46 mmol) in THF (60 mE) cooled to 00 C. was added (l3oc)20 (10.9 g, 50.0 mmol) in THF (60 mE) over 2 h. Afier stirring for 18 h at room temperature, the mixture was concentrated to dryness in vacuo and the residue was partitioned between a saturated aqueous solution of NaC1 (200 mE), and CH2C12 (400 mE). The organic phase was further washed with saturated brine (200 mE), dried over Na2SO4 and concentrated to dryness. The crude material was purified by silica gel chromatography on a Siotage HorizonTM flash chromatography system using a gradient of 5-70% methanol in 5% Et3N/CH2C12 as the eluent to give 3 (10.1 g, 27%). ?H NMR (400 MHz, CDC13) oe 1.43 (s, 9H),1.62 (m, 4H), 2.26 (s, 3H), 2.38 (t, 4H), 2.45 (bs, 3H), 2.78 (t, 3H), 3.16 (m, 2H).
1.3 g In tetrahydrofuran; at 0 - 20℃; for 16.33h; To a solution of N1-(3-aminopropyl)-N1-methylpropane-l,3-diamine (5 g, 38.48 mmol) in THF (10 mL) at 0 C was added Boc anhydride (1.50 g, 6.89 mmol) dropwise over a period of 20 min and the resulting reaction mixture was stirred at room temperature for 16 h. THF was removed under reduced pressure and the resulting mixture was poured in water (50 mL). The aqueous mixture was extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed with water, dried using anhydrous Na2S04 and concentrated under reduced pressure to get pure 2a (1.3 g, 15.4 %) as a colorless oil. NMR (400 MHz, d6-DMSO) delta 6.80- 6.79 ppm (1H, d, J=4 Hz), 3.17 (3H, broad s) 2.94-2.89ppm (2H, dd, 7=12.4, 6 Hz), 2.51 ppm (2H, broad s), 2.28-2.21ppm (4H, m), 2.08-2.07 (2H, d, 7=4 Hz), 1.50-1.44 ppm (4H, m), 1.37 (9H, s); MS (ESI-MS): m/z calcd for Ci2H26N202 [MH]+246.21,
1.3 g In tetrahydrofuran; at 0 - 20℃; for 16.3333h; To a solution of N?-(3-aminopropyl)-N?-methylpropane-1,3-diamine (5 g, 38.48 mmol) in THF (10 mL) at 0 C was added Boc anhydride (1.50 g, 6.89 mmol) dropwise over a period of 20 mm and the resulting reaction mixture was stirred at room temperature for 16 h. THF was removed under reduced pressure and the resulting mixture was poured in water (50 mL). The aqueous mixture was extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed with water, dried using anhydrous Na2SO4 and concentrated under reduced pressure to get pure 2a (1.3 g, 15.4%) as a colorless oil. ?HNMR (400 IVIHz, d6-DMSO) 6.80- 6.79 ppm (1H, d, J=4 Hz), 3.17 (3H, broad s) 2.94-2.89ppm (2H, dd, J=12.4, 6 Hz), 2.51 ppm (2H, broad s), 2.28-2.2lppm (4H, m), 2.08-2.07 (2H, d, J4 Hz), 1.50-1.44 ppm (4H, m), 1.37 (9H, s); MS (ESI-MS): m/z calcd for C,2H26N202 [MH]246.21, No mass response observed.

  • 13
  • [ 105-83-9 ]
  • [ 41840-28-2 ]
  • [ 87530-14-1 ]
YieldReaction ConditionsOperation in experiment
95% In 1,4-dioxane at 20℃; for 9h; 2.11. Synthesis of [3-[3-(Aminopropyl)methylamino]propyl]carbamic acid tert-butyl ester (9) 9 was synthesized according to the previous report [10], N,N′ -bis(3-aminopropyl)methylamine (24.8 mL, 166 mmol) was dissolved indioxane (200 mL) and S-Boc-2-mercapto-4,6-dimethylpyrimidine (10 g,42 mmol) in dioxane (160 mL) was added dropwise to this solution. Theprecipitate that formed during the dropwise addition was taken up in asmall amount of water. After stirring for 9 h, the water was evaporatedunder reduced pressure. A saturated saline solution (140 mL) was addedto the residue, followed by extraction with ethyl acetate (50 mL). Theorganic phase was dried over anhydrous MgSO4 and evaporated underreduced pressure to give 9 as a yellow viscous oil (9.7 g, 40 mmol, 95%yield). 1H NMR (500 MHz, CDCl3): δ = 1.44 (9H, s, t-Bu), 1.60-1.65 (4H,m, CH2CH2CH2N(CH3)CH2CH2CH2), 2.19 (3H, s, CH2N(CH3)CH2),2.37-2.40 (4H, m, CH2N(CH3)CH2), 2.74 (2H, t, J = 5.9 Hz, H2NCH2),3.18 (2H, q, J = 5.9 Hz, CH2NHCO), and 5.42 (1H, br, NHCO) ppm (Fig.S16). HRMS (EI+) m/z [M]+ Calcd for C12H28N3O2 246.21815, found246.21785.
32% In 1,4-dioxane at 20℃; for 20h;
25% In 1,4-dioxane
In 1,4-dioxane

  • 14
  • [ 105-83-9 ]
  • 1-Chloro-7-nitro-9-oxo-9,10-dihydro-acridine-4-carboxylic acid (2-dimethylamino-ethyl)-amide [ No CAS ]
  • C43H51N11O8 [ No CAS ]
  • 15
  • [ 105-83-9 ]
  • [ 16865-11-5 ]
  • <i>N</i>-(5,6-dichloro-1<i>H</i>-benzoimidazol-2-yl)-<i>N</i>'-[3-(5,6-dichloro-1<i>H</i>-benzoimidazol-2-ylamino)-propyl]-<i>N</i>'-methyl-propane-1,3-diamine [ No CAS ]
  • 16
  • [ 67692-91-5 ]
  • [ 105-83-9 ]
  • [ 637033-04-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 48h; 2,2, 2-Trifluoro-N-[3-(methyl{3-[(1-oxido-1, 2, 4-benzotriazin-3- yl) amino] propyl} amino) propyl] acetamide [(38).] A solution of chloride 3 (2.07 g, 11.4 mmol), [NL- (3-AMINOPROPYL) NL-METHYL-1, 3-PROPANEDIAMINE (3. 31] g, 22.8 mmol) and Et3N (3.2 mL, 22.8 mmol) in DCM (200 mL) was stirred at [20 C] for 2 d. The solvent was evaporated and the residue dissolved in [MECN] (150 mL). Ethyl trifluoroacetate (5.4 mL, 45.6 mmol) and water (0.8 mL, 45.6 mmol) added and the solution heated at reflux temperature for 16 h. The solvent was evaporated, and the residue purified by chromatography, eluting with a gradient [(0-1%) OFET3N/ (0-10%)] MeOH/DCM, followed by further chromatography, eluting with 10% MeOH/DCM, to give 1-oxide 38 (1.89 g, [43%)] as a yellow solid, mp (DCM) [111-115 C ; 1H] NMR 8 9.04 (br s, 1 H, NH), 8.25 (dd, [J=] 8.7, 1.4 Hz, 1 H, H [8'),] 7.70 (ddd, [J='8.] 4,7. 1,1. 4 Hz, 1 H, H-6'), 7.57 (d, [J=8. 4HZ, LH,] H-5'), 7.29 (ddd, [J= 8.] 7,7. 1, [1.] 1 Hz, 1 H, H- 7'), 6.17 (br s, 1 H, NH), 3. [58] (dd, J= 6.6, 5.8 Hz, 2 H, CH2N), 3.49 (br t, [J =] 6.0 Hz, 2 H, CH2N), 2.52-2. 58 (m, 4 H, 2 x [CH2N),] 2.27 (s, 3 H, [NCH3),] 1. [84-1.] 90 [(M,] 2 H, CH2), 1.75-1. 82 (m, [2 H, CH2) ;"C NMR 8 158.] 9,157. 3 [(Q,] [J= 36 HZ),] 148. 8, 135.6, 130.8, 126.4, 124.9, 120.4, 116.1 [(Q,] J= [288] Hz), 57.1, 56.4, 41.3, 40.3 (2), 26.3, 24.4 ; MS (FAB+) m/z 387 (MH+, 100%), [371] (8), [338 (30)] ; HRMS (FAB+) calcd for [C16H22F3N602] 2 m/z 387.1756, found [387.] 1765. Anal. calcd for [CI6H2IF3N602'MEOH] : C, 49.2 ; H, 5. [8] ; N, 20.9 ; found: C, 49.1 ; H, 5.5 ; N, 20.7%.
  • 17
  • [ 105-83-9 ]
  • [ 16695-22-0 ]
  • [ 655260-65-4 ]
  • 18
  • [ 105-83-9 ]
  • [ 160657-05-6 ]
  • <i>N</i>-(8-chloro-pyrrolo[1,2-<i>a</i>]quinoxalin-4-yl)-<i>N</i>'-[3-(8-chloro-pyrrolo[1,2-<i>a</i>]quinoxalin-4-ylamino)-propyl]-<i>N</i>'-methyl-propane-1,3-diamine [ No CAS ]
  • 19
  • [ 105-83-9 ]
  • [ 160657-08-9 ]
  • <i>N</i>-(7-methoxy-pyrrolo[1,2-<i>a</i>]quinoxalin-4-yl)-<i>N</i>'-[3-(7-methoxy-pyrrolo[1,2-<i>a</i>]quinoxalin-4-ylamino)-propyl]-<i>N</i>'-methyl-propane-1,3-diamine [ No CAS ]
  • 20
  • [ 105-83-9 ]
  • [ 687638-14-8 ]
  • <i>N</i>-(8-methoxy-pyrrolo[1,2-<i>a</i>]quinoxalin-4-yl)-<i>N</i>'-[3-(8-methoxy-pyrrolo[1,2-<i>a</i>]quinoxalin-4-ylamino)-propyl]-<i>N</i>'-methyl-propane-1,3-diamine [ No CAS ]
  • 21
  • [ 105-83-9 ]
  • [ 6025-69-0 ]
  • methylbis[3-({pyrrolo[1,2-a]quinoxalin-6-yl}amino)propyl]amine [ No CAS ]
  • 22
  • [ 75-77-4 ]
  • [ 105-83-9 ]
  • <i>N</i>-methyl-<i>N</i>'-trimethylsilanyl-<i>N</i>-[3-(trimethylsilanyl-amino)-propyl]-propane-1,3-diamine [ No CAS ]
  • 23
  • [ 105-83-9 ]
  • [ 576-83-0 ]
  • <i>N</i>-methyl-<i>N</i>'-(2,4,6-trimethyl-phenyl)-<i>N</i>-[3-(2,4,6-trimethyl-phenylamino)-propyl]-propane-1,3-diamine [ No CAS ]
  • 24
  • [ 105-83-9 ]
  • [ 358-23-6 ]
  • N,N-bis[(trifluoromethanesulfonamido)propyl]methylamine [ No CAS ]
  • 25
  • [ 105-83-9 ]
  • [ 5651-60-5 ]
  • bis{(5,6-dihydro-5,11-diketo-11H-indeno[1,2-c]isoquinoline)-6-propyl}methylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In chloroform; for 48h;Heating / reflux; Bis{(5.6-dihydro-5,l l-diketo-l lH-indeno[l,2-c]isoquinoline)-6- propyl}methylamine (12d). 3,3 '-Diamino-N-methyl dipropylamine (1 Id) (0.1O g, 0.69 mmol) was added to a stirred solution of indenobenzopyran 4d (0.38 g, 1.52 mmol) in C?CI3 (150 mL) and the reaction mixture was stirred under reflux for 48 h. The reaction mixture was cooled to room temperature and purified by flash column chromatography (SiO2/CHCl3 to 5% MeOH in CHCl3) to provide bisindenoisoquinoline 12d (340 mg, 82%) as a red solid: mp 230-232 C. 1H NMR (CDCl3) ? 8.67 (d, J= 8.1 Hz, 2 H), 8.30 (d, J= 7.6 Hz, 2 H), 7.72-7.66 (dt, J= 8.3 and 2.8 Hz, 4 H), 7.59 (d, J= 7.1 Hz, 2 H), 7.48-7.40 (q, J= 7.5 Hz, 4 H), 7.33 (t, J =7.3 Hz, 2 H), 4.63 (t, J= 8.0 Hz, 4 H), 2.66 (t, J= 6.5 Hz, 4 H), 2.37 (s, 3 H), 2.13-2.04 (m, 4 H); ESIMS m/z (rel intensity) 606 (MH+, 100). Anal. Calcd for C39H3 ,N3O4'0.4 CHCl3: C, 72.42; H, 4.84; N, 6.43. Found: C, 72.67; H, 5.05; N, 6.32.
  • 26
  • [ 105-83-9 ]
  • [ 68282-47-3 ]
  • <i>N</i>-methyl-<i>N</i>'-(2-phenyl-1<i>H</i>-imidazol-4-ylmethylene)-<i>N</i>-{3-[(2-phenyl-1<i>H</i>-imidazol-4-ylmethylene)-amino]-propyl}-propane-1,3-diamine [ No CAS ]
  • 27
  • [ 105-83-9 ]
  • [ 49584-26-1 ]
  • [ 950857-70-2 ]
YieldReaction ConditionsOperation in experiment
57% With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 5h; 4-Cyanobenzene-1-sulfonyl chloride (4.0 g, 19.8 mmol) was added to a solution of 3,3'-diamino-/V-methyldipropylamine (1.66 ml, 9.9 mmol) and triethylamine (3.0 ml, 21.6 mmol) in DMF (15 ml) at RT under nitrogen then stirred for 5 h. The mixture was poured into water (250 ml) and extracted with EtOAc (3 x 100 ml). The extracts were washed with water (2 x 100 ml) and brine (50 ml) before the organic phase was isolated, dried (MgSO4), filtered and concentrated. The crude product was triturated using cyclohexane, filtered and dried to afford the desired compound as a white solid. Yield: 2.69 g (57%)LC-MS (Method 2): Rt 2.31 min, m/z 476 [MH+]
57% With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 5h; 4-Cyanobenzene-1-sulfonyl chloride (4.0 g, 19.8 mmol) was added to a solution of 3,3'-diamino-lambda/-methyldipropylamine (1.66 ml, 9.9 mmol) and triethylamine (3.0 ml, 21.6 mmol) in DMF (15 ml) at RT under nitrogen then stirred for 5 h. The mixture was poured into water (250 ml) and extracted with EtOAc (3 x 100 ml). The extracts were washed with water (2 x 100 ml) and brine (50 ml) before the organic phase was isolated, dried (MgSO4), filtered and concentrated. The crude product was triturated using cyclohexane, filtered and dried to afford Intermediate 26 as a white solid. Yield: 2.69 g (57%) LC-MS (Method 2): Rt 2.31 min, m/z 476 [MH+]
  • 28
  • [ 956487-29-9 ]
  • [ 105-83-9 ]
  • [ 956487-30-2 ]
YieldReaction ConditionsOperation in experiment
43% With sodium hydrogencarbonate; In acetonitrile; at 80℃; for 3.5h; A solution of Intermediate 35 (467 mg, 0.751 mmol) in acetonitrile (15 ml) was treated with ?/,?/-<strong>[105-83-9]bis(3-aminopropyl)methylamine</strong> (54 mg, 0.375 mmol) and sodium hydrogen carbonate (252 mg, 3.00 mmol). The reaction was heated at 80sC for 3.5 h. After allowing the mixture to cool, it was filtered and the filtrate evaporated. Chromatography using an Isolute Si Il cartridge (10 g), and eluting with 1-20% MeOH in EtOAc, gave the pure product as a white solid. Yield: 182 mg (43%) LC-MS (Method 2): Rt = 3.22 min, m/z = 1136 [M+Hf
43% With sodium hydrogencarbonate; In acetonitrile; at 80℃; for 3.5h; A solution of Intermediate 35 (467 mg, 0.751 mmol) in acetonitrile (15 ml) was treated with lambda/,lambda/-<strong>[105-83-9]bis(3-aminopropyl)methylamine</strong> (54 mg, 0.375 mmol) and sodium hydrogen carbonate (252 mg, 3.00 mmol). The reaction was heated at 809C for 3.5 h. After allowing the mixture to cool, it was filtered and the filtrate evaporated. Chromatography using an Isolute Si Il cartridge (10 g), and eluting with 1-20% MeOH in EtOAc, gave the pure product as a white solid. Yield: 182 mg (43%) LC-MS (Method 2): Rt = 3.22 min, m/z = 1136 {M+H]+
  • 29
  • [ 5900-58-3 ]
  • [ 124-09-4 ]
  • [ 5162-44-7 ]
  • [ 446-48-0 ]
  • [ 7209-38-3 ]
  • [ 74-96-4 ]
  • [ 4784-77-4 ]
  • [ 22288-78-4 ]
  • [ 542-69-8 ]
  • bromomethyl resin [ No CAS ]
  • 9-fluorenyl-methoxycarbonyl-cyclohexyl alanine [ No CAS ]
  • [ 462-94-2 ]
  • [ 1458-98-6 ]
  • [ 78-77-3 ]
  • [ 1809-10-5 ]
  • [ 110-53-2 ]
  • [ 592-55-2 ]
  • [ 7328-91-8 ]
  • [ 871-76-1 ]
  • [ 105-83-9 ]
  • [ 144-48-9 ]
  • [ 929-59-9 ]
  • [ 107-59-5 ]
  • [ 5324-30-1 ]
  • [ 5428-54-6 ]
  • [ 27129-86-8 ]
  • [ 2417-72-3 ]
  • [ 2581-34-2 ]
  • [ 554-84-7 ]
  • [ 3385-21-5 ]
  • [ 126-38-5 ]
  • [ 636-93-1 ]
  • [ 88-30-2 ]
  • [ 620-13-3 ]
  • [ 823-78-9 ]
  • [ 5035-82-5 ]
  • [ 29022-11-5 ]
  • [ 539-48-0 ]
  • [ 35661-39-3 ]
  • [ 26759-46-6 ]
  • [ 20439-47-8 ]
  • [ 2615-25-0 ]
  • [ 6393-01-7 ]
  • [ 5372-81-6 ]
  • [ 35661-40-6 ]
  • [ 100-39-0 ]
  • [ 611-17-6 ]
  • [ 23915-07-3 ]
  • [ 71989-23-6 ]
  • [ 35737-15-6 ]
  • [ 2592-95-2 ]
  • [ 18880-00-7 ]
  • [ 88681-68-9 ]
  • [ 100063-22-7 ]
  • [ 75-03-6 ]
  • [ 106-94-5 ]
  • [ 104-81-4 ]
  • [ 589-10-6 ]
  • [ 107-15-3 ]
  • [ 109-76-2 ]
  • [ 110-60-1 ]
  • [ 7051-34-5 ]
  • [ 106-95-6 ]
  • [ 622-95-7 ]
  • [ 589-15-1 ]
  • [ 134-20-3 ]
  • [ 2550-36-9 ]
  • [ 89-92-9 ]
  • [ 456-41-7 ]
  • [ 766-80-3 ]
  • [ 459-46-1 ]
  • [ 874-98-6 ]
  • [ 402-49-3 ]
  • [ 870-63-3 ]
  • [ 85118-01-0 ]
  • [ 22115-41-9 ]
  • [ 3958-57-4 ]
  • [ 100-11-8 ]
  • [ 107-82-4 ]
  • [ 6482-24-2 ]
  • [ 3132-64-7 ]
  • [ 112883-41-7 ]
  • [ 3433-80-5 ]
  • [ 52727-57-8 ]
  • C18H15N2O3PolS [ No CAS ]
  • C20H20N3OPolS [ No CAS ]
  • C23H19N2O2PolS [ No CAS ]
  • C18H23ClN3OPolS [ No CAS ]
  • C22H26N3OPolS [ No CAS ]
  • C22H23N2O5PolS [ No CAS ]
  • C20H26ClN2O3PolS [ No CAS ]
  • C23H22ClN2O3PolS [ No CAS ]
  • C20H21FN3O3PolS [ No CAS ]
  • C22H29N2O3PolS [ No CAS ]
  • C21H28N3O3PolS [ No CAS ]
  • C19H26N3O4PolS2 [ No CAS ]
  • C22H30N3OPolS [ No CAS ]
  • C21H28N3O4PolS [ No CAS ]
  • C26H26N3OPolS [ No CAS ]
  • C23H15ClF3N2O2PolS [ No CAS ]
  • C24H22N3O3PolS [ No CAS ]
  • C23H16ClF2N2O2PolS [ No CAS ]
  • C22H22Br2N3OPolS [ No CAS ]
  • C24H26FN2O5PolS [ No CAS ]
  • C25H22FN2O4PolS [ No CAS ]
  • C26H22N3O4PolS [ No CAS ]
  • C25H25ClN3O3PolS [ No CAS ]
  • C25H18ClF2N2O3PolS [ No CAS ]
  • C29H26N3O3PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With piperidine; Carbonyldiimidazole; tin-2-ethylhexanoate dihydrate; potassium tert-butylate; water; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diisopropyl-carbodiimide; dibromotriphenylphosphorane; In DMF (N,N-dimethyl-formamide); dichloromethane; N,N-dimethyl acetamide; 1,2-dichloro-ethane;Combinatorial reaction / High throughput screening (HTS); EXAMPLE 1 [0213] This example shows the synthesis of a combinatorial library of thioquinazolinone derivatives. [0214] Step 1a: Preparation of Wang Bromide Resin [0215] 40 tea bags containing 2 g each of Wang resin (80 g, 120 mmol) was taken in a 5 L PP container. A solution of triphenylphosphine dibromide (152 g, 0.15 M, 3 eq., 360 mmol) in 2000 ml DCM was added and the solution was shaken at room temperature overnight. The resin was sequentially washed with DCM (4×, 1.5 L each) and diethylether (6×, 1.5 L each) and dried under vacuum, to give the bromo wang resin. [0216] Step 1b: Loading of the Nitrophenol on Bromo Wang [0217] 20 g of the Bromo wang resin (1.5 meq/g) was taken in a 2 L wide-mouthed glass container and 1000 mL DMA was addded to it followed by the addition of the nitro phenol (10 eq., 0.3M, 300 mmol). Potasium t-butoxide (33.46 g, 10 eq., 300 mmol) was then added to it and the bottles were heated at 50 C. overnight. The bags were washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The tea bags were then dried overnight in air. The following nitrophenols were used: [0218] 2-METHYL-5-NITROPHENOL [0219] 5-HYDROXY-2-NITROBENZOTRIFLUORIDE [0220] 3-METHYL-4-NITROPHENOL [0221] 2-METHOXY-5-NITROPHENOL [0222] M-NITROPHENOL [0223] Step 1c: Reduction of the Nitro Group to Amine [0224] A 2.0 M solution of tin-2-ethylhexanoate dihydrate was prepared in DMF containing 0.5% H2O. The tea bags were added and the solution is heated at 50 C. for 40 hours. After cooling the bags are washed with DMF/10% HOAc (3×), DMF (3×), 5% DIEA/DCM (2×), DCM (2×) and MeOH (2×) and dried in air overnight. [0225] Step 1d: Coupling N-FMOC Protected Amino Acid to Wang Resin. [0226] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL plastic bottle. DMF (300 mL), DCM (300 mL), FMOC-Cyclohexyl alanine (70.82 g, 6 eq., 0.3M, 180 mmol), DIC (22.71 g, 6 eq., 180 mmol), HOBt (24.32 g, 6 eq., 180 mmol) were added sequentially. After shaking for 12 hours, the packet was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried overnight in air. The tea bags containing the amino acids were then treated with 20% piperidine/DMF for 2 h at room temperature to deblock the FMOC group. The following amino acids were used: [0227] FMOC-GLY-OH [0228] FMOC-ALA-OH [0229] FMOC-L-ISOLEUCINE [0230] FMOC-L-PHENYLALANINE [0231] FMOC-D-NLE-OH [0232] FMOC-CHA-OH [0233] FMOC-L-TRYPTOPHAN [0234] Step 1e: Coupling of the Diamines to Wang Resin [0235] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL Nalgene bottle. 600 mL of DCM was added followed by the addition of the carbonyl diimidazole (29.9 g, 6 eq., 0.3M, 180 mmol) and the flasks were shaken at room temperature for 3 hours after which they were decanted and washed with DCM (2×, 600 mL). To these Nalgene bottles were added the diamines (6 eq., 0.4M, 180 mmol) in 450 mL of DCM (0.4M) and they were shaken at room temperature overnight. The diamines used were as follows: [0236] 2,2-DIMETHYL-1,3-PROPANEDIAMINE [0237] 1,3-CYCLOHEXANEDIAMINE [0238] (1R,2R)-(-)-1,2-DIAMINOCYCLOHEXANE [0239] TRANS-1,4-DIAMINOCYCLOHEXANE [0240] P-XYLYLENEDIAMINE [0241] 1,4-BIS(3-AMINOPROPYL)PIPERAZINE [0242] ETHYLENEDIAMINE [0243] 1,3-DIAMINOPROPANE [0244] 1,8-DIAMINO-3,6-DIOXAOCTANE [0245] 1,4-DIAMINOBUTANE [0246] 1,5-DIAMINOPENTANE [0247] 1,6-HEXANEDIAMINE [0248] N,N-BIS(3-AMINOPROPYL)METHYLAMINE [0249] 2,2'-THIOBIS(ETHYLAMINE) [0250] 2,5-DIMETHYL-1,4-PHENYLENEDIAMINE [0251] After shaking overnight, the packets was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried in air. [0252] Step 2: Formation of the Isothiocyanate [0253] The o-amino benzoate ester (136 g, 10 eq., 900 mmol) was taken in a 5 L wide-mouthed glass bottle and 2.7 L of dichloroethane was added to it (0.3M). The following esters were used: [0254] METHYL ANTHRANILATE [0255] METHYL 2-AMINO-4-CHLOROBENZOATE [0256] 2-AMINO-4,5-DIMETHOXYBENZOIC ACID [0257] METHYL ESTER [0258] METHYL 3,4,5-TRIMETHOXYANTHRANILATE [0259] DIMETHYL AMINOTEREPHTHALATE [0260] METHYL 2-AMINO-5-BROMOBENZOATE [0261] METHYL 3-AMINOTHIOPHENE-2-CARBOXYLATE [0262] METHYL 3-AMINO-5-PHENYLTHIOPHENE-2-CARBOXYLATE [0263] Thiocarbonyl diimidazole (160 g, 10 eq., 900 mmol) was added to it and the solution was heated at 55 C. overnight to form the isothiocyanate. [0264] Step 3: Formation of the Thioquinazolinone [0265] The next day the tea bags containing the amino acids, diamines and the amino phenols on wang resin (90 mmol) was added to the isothiocyanate solution from reaction 2 and the glass bottles were heated at 55 C. overnight. After cooling the bags was washed alternatively with DMF (2000 mL) and DCM (2000 mL) 3 cycles followed by 6 cycles of MeOH...
  • 30
  • C38H32Cl2N12O10S2(2-)*2Na(1+) [ No CAS ]
  • [ 105-83-9 ]
  • C52H70N18O10S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
18.8 G (0.13 mol) of N, N-bis (3-aminopropyl) METHYLAMINE in 100 ML of water and 100 ML of dioxane are introduced into a 350 ml sulfonation flask equipped with a condenser and pH meter. At 70-75C, 22.7 G (0.021 mol) of the intermediate of formula (105a) prepared according to Example 1. 6 are introduced. The yellow solution is stirred for 3 h at 86-88C. After cooling to 70C, the solution is then diluted with 120 ml of water and adjusted to pH 4.5 with 35 ml of conc. hydrochloric acid. After addition of 100 ML of acetone, the precipitate is filtered through a suction filter, washed with water and dried IN VACUO at 70C. Yield : 28.7 G
  • 31
  • [ 105-83-9 ]
  • [ 110-21-4 ]
  • [ 81779-01-3 ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one; water; EXAMPLE 10 72.5 g of bis-(3-aminopropyl)-methylamine and 120 g of hydrazodicarbonamide are stirred in 300 ml of N-methyl pyrrolidone for 2 hours at 175 C. and for 3 hours at 200 C. The reaction product is concentrated in vacuo, dissolved in water and precipitated with isopropanol giving a colourless product which could not be crystallized. For characterisation and purification, the product is dissolved in water, the resulting solution is adjusted to pH 2 with concentrated HCl and subsequently concentrated in vacuo. The residue is recrystallized from ethanol, giving 112 g (65% of the theoretical) of bis-[3-(3,5-dioxo,1,2,4-triazolidin-4-yl)-propyl]-methylamine hydrochloride in the form of colourless crystals melting at 238 C. IR (KBr): 1763, 1698 cm-1 (C=O)
  • 32
  • [ 1871-76-7 ]
  • [ 105-83-9 ]
  • N-(3-{Methyl-13-(N'-cyano-N"-pyridin-4-yl-guanidino)propyl]-amino}-propyl)-2,2-diphenyl-acetamide [ No CAS ]
  • 3-amino-3'-diphenylacetylamino-N-methyldipropylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In pyridine; EXAMPLE 19 N-(3-{Methyl-13-(N'-cyano-N"-pyridin-4-yl-guanidino)propyl]-amino}-propyl)-2,2-diphenyl-acetamide (SBR-11-4491) was synthesised as follows To a solution of 3,3'-diamino-N-methyldipropylamine (3.05 g, 21.0 mmol, 7.0 equiv.) in 10 mL pyridine at room temperature was added slowly diphenylacetyl chloride (0.692 g, 3.0 mmol, 1.0 equiv.). The reaction mixture was stirred at room temperature overnight, diluted with 100 mL EtOAc, and washed with 3*40 mL water to wash away excess starting material. The organic layer was washed with 30 mL brine, dried over K2CO3, and concentrated to yield 3-amino-3'-diphenylacetylamino-N-methyldipropylamine as viscous yellow oil (crude 0.82 g, 80%, 2.40 mmol). [M+H] calculated: 340.24, found: 340.2.
  • 33
  • [ 105-83-9 ]
  • [ 2251-50-5 ]
  • [ 918776-74-6 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; In chloroform; EXAMPLES; Synthesis of crosslinkers:; Synthesis of I:; 3,3'-diamino-N-methyldipropylamme (0.29 mL,1.79 mmol, Aldrich) and triethylamine (0.55 mL, 3.93 mmol, Aldrich) were dissolved in 40 mL anhydrous CHCl3 and added dropwise to perfluorobenzoyl chloride (0.54 mL, 3.93 mmol, Aldrich) in another 40ml anhydrous CHCl3. The white precipitate of triethylammonium chloride by-product was filtered off, the filtrate washed with 3x25 mL of half-saturated NaCl solution, then dried with MgSO4, and evaporated to give N-methyl-N,N-dipropylene bis(pentafiuorobenzamide) as colorless liquid (yield, 75%). This was then dissolved (777 mg, 1.34 mmol) in 3.2 mL acetone and reacted with 10% excess sodium azide (192 mg, 2.95 mmol) dissolved in 1.5 mL water and 3 mL acetone, under reflux for 5-8hours. Excess acetone was added, the white precipitate of NaF was filtered off, and the yellow filtrate washed with 3x25 mL of half saturated NaCl solution, dried with MgSO4, and evaporated to give N-methyl-LambdaxiJV-dipropylene bis(4-azido-2,3,5,6-tetrafluorobenzamide) as a pale yellow solid (yield, 65%). This was then dissolved (505 mg, 0.87 mmol) in 10 mL anhydrous CHCl3, and reacted with excess iodomethane (5 mL, 80.3 mmol) overnight at room temperature. The fine pale yellow precipitate was filtered off and recrystallized twice in water to give N,N-dimethyl-izetaN-dipropylene bis(4-azido-2,3,5,6- tetrafluorobenzamide) ammonium iodide (I) as pale yellow crystals (yield, 55%). 1H NuMR (ppm, MeOD) = 4.56 (s), 3.50 (t, J=6.6Hz, 2H), 3.42 (m, 2H), 3.15 (s, 3H), 2.12 (m, 2H). 19F NuMR (ppm, MeOD) = -68.35 (d, J=25Hz), -76.97 (d, J=24Hz). FTIR (cm" l) = 3300 (NH), 3078 (NH), 3032 (NH), 2968 (CH3), 2942 (CH2), 2885 (CH2), 2157- 2129 (N3), 1658 (CO), 1549 (CONH), 1486 (N3), 1437 (CH2), 1407 (CH3, CH2), 1338 (N3), 1278 (N3), 1024, 1000, 989.
  • 34
  • [ 864228-16-0 ]
  • [ 105-83-9 ]
  • C47H43F6N9O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2.5h; Example 5; Intermediate 4 (117 g, 0.292 mmol), 3,3'-diamino-N-methyldipropylamine (21 mg, 0.146 mmol) and DIPEA (254 mul, 1.46 mmol) were dissolved in DMF (6 ml). HATU (133 mg, 0.350 mmol) was added and the solution was allowed to stand at RT for 2.5 h. The DMF was evaporated and the residue was dissolved in EtOAc (100 ml). The organic solution was washed with aqueous NaHCO3 (60 ml), water (50 ml) and brine (40 ml). After drying (Na2SO4), the solvent was removed and the crude product was purified using HPLC (System 1). Yield: 38 mg (14%) LC-MS (Method 1): Rt 7.92 min, m/z 912.23 [MH+]
  • 35
  • [ 14220-65-6 ]
  • [ 105-83-9 ]
  • [ 15391-24-9 ]
  • 36
  • [ 105-83-9 ]
  • [ 6147-53-1 ]
  • [ 90-02-8 ]
  • [ 15391-24-9 ]
  • 37
  • sodium hexaflorophosphate [ No CAS ]
  • copper(II) nitrate monohydrate [ No CAS ]
  • [ 105-83-9 ]
  • [ 68282-53-1 ]
  • [Cu(CH3N(C3H6NCHC3H2N2CH3)2)](2+)*2PF6(1-)=[Cu(CH3N(C3H6NCHC3H2N2CH3)2)](PF6)2 [ No CAS ]
  • 38
  • [ 7791-07-3 ]
  • copper(II) nitrate monohydrate [ No CAS ]
  • [ 105-83-9 ]
  • [ 68282-53-1 ]
  • [Cu(CH3N(C3H6NCHC3H2N2CH3)2)](2+)*2ClO4(1-)*H2O=[Cu(CH3N(C3H6NCHC3H2N2CH3)2)](ClO4)2*H2O [ No CAS ]
  • 39
  • copper(II) choride dihydrate [ No CAS ]
  • [ 105-83-9 ]
  • sodium perchlorate [ No CAS ]
  • [ 68282-47-3 ]
  • [Cu(N,N'-bis((2-phenylimidazol-4-yl)methylene)-3,3-diaminodipropylmethylamine)](ClO4)2 * 0.5 H2O [ No CAS ]
  • 40
  • ethyl (4R)-6-(bromomethyl)-4-(4-cyanophenyl)-2-oxo-1-[3-(trifluoromethyl)-phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate [ No CAS ]
  • [ 105-83-9 ]
  • [ 956486-48-9 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine; In tetrahydrofuran; at 20℃; for 17.5h; Intermediate 26Intermediate 5 (108.6 g, 0.217 mol) was dissolved in THF (1500 ml) and triethylamine (240 ml, 1.74 mol) was added, followed by a solution of lambda/,lambda/-bis(3- aminopropyl)methylamine (23.55 g, 0.162 mol) in THF (100 ml) dropwise over 30 min. The reaction was stirred at RT for 17 h and the volume was reduced to 300-400 ml. Water (3000 ml) was added and the mixture was stirred vigorously for 90 min. The supernatant was decanted off and a further amount of water (3000 ml) was added. Stirring was continued for 30 min. The water was decanted off and the remaining solid was dissolved in EtOAc (1500 ml). The solution was dried(Na2SO4), evaporated to a small volume, and poured into Et2O with vigorous stirring. The white precipitate was filtered off and washed with Et2O and dried in vacuo.Yield: 86.0 g (88%)Further purification was achieved by crystallization from either n-butanol or n- propanol.LC-MS (Method 4): Rt = 7.88 min, m/z = 908.44 [M+H]+
88% With triethylamine; In tetrahydrofuran; at 20℃; for 17.5h; Intermediate 5 (108.6 g, 0.217 mol) was dissolved in THF (1500 ml) and triethylamine (240 ml, 1.74 mol) was added, followed by a solution of /V,lambda/-bis(3- aminqpropyl)methylamine (23.55 g, 0.162 mol) in THF (100 ml) dropwise over 30 min.The reaction was stirred at RT for 17 h and the volume was reduced to 300-400 ml.Water (3000 ml) was added and the mixture was stirred vigorously for 90 min. The supernatant was decanted off and a further amount of water (3000 ml) was added. Stirring was continued for 30 min. The water was decanted off and the remaining solid was dissolved in EtOAc (1500 ml). The solution was dried (Na2SO4), evaporated to a small volume, and poured into Et2O with vigorous stirring. The white precipitate was filtered off and washed with Et2O and dried in vacuo.Yield: 86.0 g (88%) Further purification was achieved by crystallization from either n-butanol or n-propanol.LC-MS (Method 4): Rt = 7.88 min, m/z = 908.44 [M+H]+
  • 41
  • [ 105-83-9 ]
  • [ 265312-60-5 ]
  • [ 890649-32-8 ]
YieldReaction ConditionsOperation in experiment
36% In ethanol; at 60℃; for 2h; Example 1 5.5'-[(methylimino)bis(propane-3,1-diylimino)]bis(2-methyl-1,3-benzothiazole-4,7-dione) 83.4 mg (0.57 mmol; 0.6 equivalents) of N-(3-aminopropyl)-N-methylpropane-1,3-diamine are added to 200 mg (0.95 mmol) of 5-methoxy-2-methyl-4,7-dioxobenzothiazole in solution in 15 ml of anhydrous ethanol. The reaction mixture is stirred at 60 C. for 2 hours, then the solvent is evaporated off under reduced pressure. The residue is purified on a silica column (eluent: methanol at 3% in dichloromethane) and 30 mg (yield=36%) of expected product is obtained in the form of a red powder. Melting point: 94-96 C. NMR 1H (DMSO d6, 400 MHz, delta): 7.93 (t, 2H, 2NH); 5.40 (s, 2H, 2CH); 3.20-3.15 (m, 4H); 2.72 (s, 6H, 2CH3); 2.40-2.37 (m, 4H); 2.17 (s, 3H, CH3); 1.76-1.73 (m, 4H). MS-LC: MH+=500.15; r.t.=7.49 min.
  • 42
  • [ 105-83-9 ]
  • 5-methoxy-1,3-benzothiazol-4,7-dione [ No CAS ]
  • [ 1346864-08-1 ]
YieldReaction ConditionsOperation in experiment
26% In ethanol; at 85℃; for 1.5h; 25.4) 5.5'-[(methylimino)bis(propane-3,1-diylimino)]bis(1,3-benzothiazole-4,7-dione) 57 mul (0.37 mmol; 0.48 equivalent) of N-(3-aminopropyl)-N-methylpropane-1,3-diamine is added to 150 mg (0.77 mmol) of 5-methoxy-1,3-benzothiazol-4,7-dione in solution in 6 ml of ethanol. The reaction mixture is maintained under stirring at 85 C. for 90 minutes, then the solvent is evaporated off under reduced pressure and the expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 94/6) and 95 mg (yield=26%) of 5.5'-[(methylimino)bis(propane-3,1-diylimino)]bis(1,3-benzothiazole-4,7-dione) is obtained in the form of a red powder. Melting point: 223-224 C. NMR 1H (DMSO d6, 400 MHz, delta): 9.28 (s, 2H); 8.02 (t, 2H, 2NH); 5.48 (s, 2H); 3.24-3.19 (m, 4H); 2.42-2.38 (m, 4H); 2.18 (s, 3H, CH3); 1.78-1.74 (m, 4H). MS-LC: MH+=472.19; r.t.=7.32 min.
  • 43
  • [ 20485-43-2 ]
  • [ 105-83-9 ]
  • [ 57294-38-9 ]
  • [ 128293-64-1 ]
  • [ 77716-11-1 ]
  • [ 1186017-44-6 ]
  • 44
  • [ 105-83-9 ]
  • [ 1234366-99-4 ]
  • [ 1234368-02-5 ]
YieldReaction ConditionsOperation in experiment
74% With triethylamine; In dichloromethane; at 20℃; for 3h; To a solution of Nl-(3-aminopropyl)-Nl-methyIpropane-l,3-diamme (560 mg, 3.85 mmol) dissolved in DCM (20 mL), was added triethylamine (300 mg, 2 96 mmol) and 3-(6,8-dichloro-2-5 methyl-l,2,3,4-tetrahydroisoqumolin-4-yl)benzene-l-sulfonyl chloride (300 mg, 0.77 mmol). The resulting solution was stirred for 3 h at room temperature After removing the solvent, the resulting residue was diluted with EtOAc (50 mL), washed with water (2x10 mL) and d?ed over anhydrous sodium sulfate. The crude product was purified by Flash-Prep-HPLC with H2O MeOH (1.4) to afford 300 mg (74%) of N-(3-((3-0 ammopropyl)(methyl)armno)propyl)-3-(6,8-dichloro-2-methyl-l, 2,3,4- tetrahydroisoquinolin-4-yl)benzenesulfonamide as a yellow oil.
  • 45
  • [ 881890-07-9 ]
  • [ 105-83-9 ]
  • [ 1276655-59-4 ]
YieldReaction ConditionsOperation in experiment
16% With sodium carbonate; mercury dibromide; In ethanol; toluene; at 135℃; for 2h; General procedure: To a solution of 5 (173 mg, 0.5 mmol) in anhydrous dichloromethane (5 mL) was added 4 M HCl in 1,4-dioxane (5 mL) and the resulting mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated and the crude product hydrochloride was used in the next step without further purification. Alternatively, N-Me-N-(3-propylamino)propanediamine is also commercially available. A mixture of 2,3-dihydropyrrolo[2,1-b]quinazoline-9(1H)-thione 16a19 (202 mg, 1 mmol), N-Me-N-(3-propylamino) propanediamine (0.08 mL, 0.5 mmol; alternatively 0.5 mmol of the hydrochloride obtained as described above), and sodium carbonate (318 mg, 3 mmol) was refluxed in ethanol (10 mL)/toluene (10 mL) in an 135 C oil bath, and finely grinded mercury(II) bromide (0.72 g, 0.2 mmol) was added. The mixture was heated and stirred vigorously for 2 h. The mixture was then filtered and the filtrate concentrated. The crude product obtained was purified by column chromatography (chloroform/methanol/ammonia, 7:1:0.1).
  • 46
  • [ 105-83-9 ]
  • [ 50441-50-4 ]
  • [ 1276655-57-2 ]
YieldReaction ConditionsOperation in experiment
36% With sodium carbonate; mercury dibromide; In ethanol; toluene; at 135℃; for 2h; To a solution of 5 (173 mg, 0.5 mmol) in anhydrous dichloromethane (5 mL) was added 4 M HCl in 1,4-dioxane (5 mL) and the resulting mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated and the crude product hydrochloride was used in the next step without further purification. Alternatively, N-Me-N-(3-propylamino)propanediamine is also commercially available. A mixture of 2,3-dihydropyrrolo[2,1-b]quinazoline-9(1H)-thione 16a19 (202 mg, 1 mmol), N-Me-N-(3-propylamino) propanediamine (0.08 mL, 0.5 mmol; alternatively 0.5 mmol of the hydrochloride obtained as described above), and sodium carbonate (318 mg, 3 mmol) was refluxed in ethanol (10 mL)/toluene (10 mL) in an 135 C oil bath, and finely grinded mercury(II) bromide (0.72 g, 0.2 mmol) was added. The mixture was heated and stirred vigorously for 2 h. The mixture was then filtered and the filtrate concentrated. The crude product obtained was purified by column chromatography (chloroform/methanol/ammonia, 7:1:0.1). The pure compound was obtained as a yellow grease (36 %). 1H NMR (CDCl3, 400 MHz) delta: 1.83-1.88 (m, 4H, CH3N(CH2CH2CH2N)2), 2.02-2.07 (m, 4H, 2 × NCH2CH2), 2.28 (s, 3H, NCH3), 2.56 (t, 4H, J = 7.62 Hz, 2 × N(CH3)CH2), 2.93 (t, 4H, J = 7.86 Hz, 2 × CH2C), 3.80 (t, 4H, J = 6.47 Hz, 2 × CH2N), 3.88 (t, 4H, J = 7.08 Hz, 2 × NCH2), 7.06-7.12 (m, 2H, 2 × C(7)H), 7.39-7.41 (m, 4H, 2 × C(6, 8)H), 8.03 (d, 2H, J = 8.26 Hz, 2 × C(5)H) ppm. 13C NMR (CDCl3, 400 MHz) delta: 18.71, 30.77, 32.83, 42.82, 48.23, 48.61, 55.57, 119.83 (arom), 123.81 (arom), 126.78 (arom), 128.05 (arom), 131.58 (arom), 145.33 (arom), 148.85 (arom), 160.17 (arom) ppm. ESI-MS m/z 482 [M+H]+. Elem. Anal. Calcd for (C29H35N7·0.3CH2Cl2·0.6CH3OH): C, 68.23; H, 7.28; N, 18.63. Found: C, 67.88; H, 7.45; N, 18.72.
  • 47
  • [ 13139-17-8 ]
  • [ 105-83-9 ]
  • [ 1307864-23-8 ]
YieldReaction ConditionsOperation in experiment
In chloroform; at 20℃; for 16h; a) Compound 11a[0271] A solution of N,N-bis(3-aminopropyl)methyl amine (lg, 6.9 mmoles) in chloroform (40 mL) was treated with benzyloxycarbonylsuccimmide (3.78 g, 2.2 equivalents). The reaction was stirred at room temperature for 16 hours. TLC analysis on silica of the reaction mixture using 15% methanol in ethyl acetate showed the formation of a polar product in a clean reaction. The reaction mixture was diluted with chloroform (40 mL) and washed with saturated aqueous sodium bicarbonate solution. It was then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a viscous oil that solidified upon storage to a waxy solid. Yield = 3.2 g; MALDI-TOF MS 414.4 observed.
In chloroform; at 20℃; for 16h; Example 8[0220] Synthesis of Z-diamine, compound 8c and Z-Di-NHS, compound 8d; [0221] a) Compound 8a[0222] A solution of N,N-bis(3-aminopropyl)methyl amine (lg, 6.9 mmoles, TCI) in chloroform (40 mL) was treated with benzyloxycarbonylsuccinimide (3.78 g, 2.2 equivalents). The reaction was stirred at room temperature for 16 hours. TLC analysis on silica of the reaction mixture using 15% methanol in ethyl acetate showed the formation of a polar product in a clean reaction. The reaction mixture was diluted with chloroform (40 mL) and washed with saturated aqueous sodium bicarbonate solution. It was then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a viscous oil that solidified upon storage to a waxy solid. Yield = 3.2 g; MALDI-TOF MS 414.4 observed.
  • 48
  • [ 105-83-9 ]
  • [ 162758-35-2 ]
  • [ 1338604-44-6 ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In tetrahydrofuran; at 20℃; for 16h; N-{3-[(3-ammopropyl)(methyl)amino]propyl}-5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4- methyl-lH-pyrazole-3-carboxamide: H NMR (300 MHz, CHLOROFORM- ) d ppm 1.53 - 1.69 (m, 2 H) 1.77 (t, J=6.62 Hz, 2 H) 2.15 - 2.23 (m, 3 H) 2.34 - 2.50 (m, 7 H) 2.66 - 2.75 (m, 2 H) 3.45 - 3.53 (m, 2 H) 7.03 - 7.09 (m, 2 H) 7.23 - 7.35 (m, 3 H) 7.43 (dd, J=2.05, 0.54 Hz, 1 H) 7.75 (t, J=5.37 Hz, 1 H).; Benzotriazole-l-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (leq) was added to a solution of 5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-lH-pyrazole-3- carboxylic acid (1 eq), and diamine (5 eq) in tetrahydrofuran (THF). The reaction mixture was stirred for 16 h. Ethyl acetate was added and the solution was washed with 2 N sodium hydroxide and brine. The organic layer was dried with magnesium sulfate. The solution was then filtered and concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-100% CMA 80/efhyl acetate to yield pure amino- lH-pyrazole-3- carboxamides.
  • 49
  • [ 105-83-9 ]
  • [ 35034-22-1 ]
  • [ 1432473-78-3 ]
YieldReaction ConditionsOperation in experiment
In methanol at 50℃; for 0.25h; Inert atmosphere; 2 2.2 Synthesis of ligand bis(N,N′-2-methylimidazol-4-yl-methylideneaminopropyl)methylamine (abbreviated as H2L1) To a solution of N,N′-bis(3-aminopropyl)methylamine (0.072g, 0.5mmol) in 10mL of methanol was added a solution of 2-methyl-4-formylimidazole (0.110g, 1mmol) in 10mL of methanol at room temperature. The resulting solution was warmed at 50°C under stirring for 15min and then cooled to room temperature. The ligand solution was used for the synthesis of the FeII complex without further purification.
  • 50
  • [ 105-83-9 ]
  • [ 1448724-50-2 ]
  • [ 1448724-51-3 ]
YieldReaction ConditionsOperation in experiment
63.9% In methanol; at 140℃; for 0.5h;Microwave irradiation; A mixture of methyl 2-(3-(1 -(benzyloxy)-2,2,2-trifluoroethyl)benzyl)-4-chloro-9H-pyrimido[4,5- b]indole-7-carboxylate (0.375 g, 0.695 mmol) and N1 -(3-aminopropyl)-N1 -methylpropane-1 ,3-diamine (0.784 mL, 4.86 mmol) in MeOH (9.83 mL, 243 mmol) was heated in a microwave oven to 140C for 30 minutes. Then, after concentration to dryness under reduced pressure the resulting brown oil was purified by flash chromatography to afford methyl 4-((3-((3-aminopropyl)(methyl)amino)propyl)amino)-2- (3-(1 -(benzyloxy)-2,2,2-thfluoroethyl)benzyl)-9H-pyhmido[4,5-b]indole-7-carboxylate (288 mg, 63.9% yield) as a yellow foam: H NMR (400 MHz, DMSO-d6) delta ppm 1.48 (dt, J=14.0, 6.9 Hz, 2 H) 1 .75 (quin, J=6.7 Hz, 2 H) 2.14 (s, 3 H) 2.24 - 2.42 (m, 4 H) 2.52 - 2.60 (m, 2 H) 3.61 (q, J=6.3 Hz, 2 H) 3.88 (s, 3 H) 4.10 (s, 2 H) 4.49 (s, 2 H) 5.17 (q, J=7.0 Hz, 1 H) 7.18 - 7.30 (m, 5 H) 7.31 - 7.36 (m, 1 H) 7.39 (t, J=7.6 Hz, 1 H) 7.44 - 7.53 (m, 2 H) 7.58 (t, J=5.3 Hz, 1 H) 7.84 (dd, J=8.2, 1.4 Hz, 1 H) 8.00 (d, J=1 .4 Hz, 1 H) 8.28 (d, J=8.2 Hz, 1 H); MS m/z 649.3 (M+H)+; HPLC 97.6% 220 nm and 95.5% 254 nm, RT = 1.96 minutes.
  • 51
  • [ 105-83-9 ]
  • [ 1448724-61-5 ]
  • [ 1448724-14-8 ]
  • [ 1448724-21-7 ]
YieldReaction ConditionsOperation in experiment
67.2%; 6.71% In methanol; at 140℃; for 0.5h;Microwave irradiation; In a 2-5 mL microwave vial was added methyl 2-benzyl-4-chloro-9H-pyrimido[4,5-b]indole-7- carboxylate (0.050 g, 0.142 mmol) and A/1 -(3-aminopropyl)-A/1 -methylpropane-1 ,3-diamine (0.115 mL, 0.711 mmol) in MeOH (2.000 mL, 49.4 mmol) to give a tan suspension. The vial was placed in the microwave and heated to 140C for 30 min. After 30 minutes, the mixture was concentrated to dryness on a rotavap. and the residue was purified by flash chromatography and lyophilized from CH3CN to afford two distinct products: Example 45 as the mono-N-alkylated product: methyl 4-((3-((3- aminopropyl)(methyl)amino)propyl)amino)-2-benzyl-9H-pyrimido[4,5-b]indole-7-carboxylate (44 mg, 67.2% yield) as a white solid; H NMR (400 MHz, DMSO-d6) delta ppm 1 .44 (dt, J=13.8, 6.6 Hz, 2 H) 1 .72 (dt, J=13.7, 6.8 Hz, 2 H) 2.11 (s, 3 H) 2.24 - 2.30 (m, 2 H) 2.33 (t, J=6.7 Hz, 2 H) 2.47 (br. s., 2 H) 3.51 - 3.61 (m, 2 H) 3.76 - 3.85 (m, 3 H) 3.97 (s, 2 H) 7.08 - 7.15 (m, 1 H) 7.17 - 7.24 (m, 2 H) 7.27 - 7.34 (m, 2 H) 7.50 (t, J=5.3 Hz, 1 H) 7.76 (dd, J=8.2, 1.6 Hz, 1 H) 7.92 (d, J=1.6 Hz, 1 H) 8.20 (d, J=8.2 Hz, 1 H); MS m/z 461.2 (M+H)+; HPLC >99%, RT = 1 .63 minutes. Example 51 as a bis-alkylated product: dimethyl 4,4'-(((methylazanediyl)bis(propane-3,1- diyl))bis(azanediyl))bis(2-benzyl-9H-pyrimido[4,5-b]indole-7-carboxylate) (3.7 mg, 6.71 % yield) as a light yellow solid: H NMR (400 MHz, DMSO-de) delta ppm 1 .18 - 1 .29 (m, 4 H) 1.79 - 1.91 (m, 4 H) 2.25 (s, 3 H) 3.58 - 3.71 (m, 4 H) 3.84 (s, 6 H) 3.97 (s, 4 H) 7.07 - 7.16 (m, 2H) 7.22 (t, J=7.4 Hz, 4 H) 7.29 - 7.34 (m, 4 H) 7.53 (t, J=5.3 Hz, 2 H) 7.77 (dd, J=8.2, 1 .4 Hz, 2 H) 7.96 (d, J=1.4 Hz, 2 H) 8.22 (d, J=8.2 Hz, 2 H) 12.01 (s, 2H); MS m/z 776.3 (M+H)+; HPLC 94.6% 220 nm and 93.8% 254 nm, RT = 2.01 minutes.
  • 52
  • [ 105-83-9 ]
  • [ 814-68-6 ]
  • [ 158749-62-3 ]
YieldReaction ConditionsOperation in experiment
29% With sodium hydroxide; In water; acetonitrile; at 20℃; for 6h;Cooling with ice; Synthesis of Specific Polymerizable Compound 3- (0257) To a one-liter three-necked flask equipped with a stirrer, 50.0 g (344 mmol) of N,N-<strong>[105-83-9]bis(3-aminopropyl)methylamine</strong>, 55.0 g (1.4 mol) of sodium hydroxide, 300 mL of water, and 450 mL of acetonitrile were added. Then, while cooling in an ice bath, 65.6 g (725 mmol) of acrylic acid chloride was added thereto dropwise. After the addition was completed, the temperature of the mixture was elevated to room temperature, and the mixture was further stirred for 6 hours. Then, from the resulting reaction liquid, acetonitrile was distilled off under reduced pressure. Thereafter, the aqueous layer was extracted 3 times with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and then filtered. Thereafter, ethyl acetate was distilled off under reduced pressure, thereby obtaining 25.4 g (100 mmol, yield: 29%) of specific polymerizable compound 3.
  • 53
  • [ 86-98-6 ]
  • [ 105-83-9 ]
  • [ 947699-89-0 ]
YieldReaction ConditionsOperation in experiment
67% at 80 - 100℃; General procedure: A combined method, as described by Biot et al.30 and N?Da et al.31 were used. 4,7-dichloroquinoline (15.1mmol, 3g, 1equiv) and diamine (0.15mol, 10equiv) were reacted for 3-6h at 80-100C [Scheme 1, step (i)]. The reaction mixture was allowed to cool and neutralized with an aqueous solution of 1M NaOH. The product was extracted with hot ethyl acetate, washed with water, dried over MgSO4 and evaporated to dryness under reduced pressure to produce the desired pure compound in high yields (51-85%), unless stated otherwise.32 In the reaction involving piperazine and leading to 4-amino-7-chloroquinoline 9, acetonitrile was used as solvent. The yields, melting points, IR, NMR, and HRMS data are reported.
  • 54
  • [ 105-83-9 ]
  • C17H13ClNO2(1+)*I(1-) [ No CAS ]
  • [ 1587729-29-0 ]
YieldReaction ConditionsOperation in experiment
95% at 120℃; for 0.5h; 0.3mol of chloroacetic acid dissolved in 60ml of water, adjusted to pH 9 with sodium hydroxide, then add 0.2mol of p-methoxy phenol, l0 C reflux, the compound T1,Followed by addition of thionyl chloride for chlorination reaction to obtain compound T2,Steamed to the thionyl chloride solvent to brown liquid, and then with anthranilic acid condensation reaction, obtained T3,Then PPA preheated to 130 C by adding T3 for the chemical reaction,The compound T4 was obtained. The T4 was reacted with thionyl chloride at 80 C under reflux,To obtain compound T5. Then, the purified T5 was methylated with methyl iodide in the system of sulfolane as the solvent to obtain the compound T6,T6-2 was added to a one-Using ethylene glycol ether as solvent,And N, N-bis (3-aminopropyl) methylamine at 120 C for 30min, and finally adding a large number of anhydrous ether, precipitate precipitation, filter drying compounds 4T7.
1.36 g In 2-methoxy-ethanol; at 120℃; for 0.5h; A solution of 1c (1g, 3.52mmol) in tetramethylene sulfone (10mL) was treated with iodomethane (10mL, 159.0mmol) and was heated at 68C for 3 days. After cooling to room temperature, the mixture was poured into ether. The solution was filtered, and the filtrate was extracted with ether (3×10mL). Then the filtrate was dried under infrared light to afford crude product. The above crude product in 2-methoxyethanol (10mL) was treated with N,N-bis(3-aminopropyl) methylamine (10mL, 62.05mmol), and heated at 120C for 30min. After cooling to room temperature, the mixture was poured into ether. The solution was filtered, and extracted with ether (3×10mL). The solvent was evaporated, and the residue was dried under infrared light to afford product 7 (1.36g) as a pale yellow solid in 95% yield. mp 168-170C. 1H NMR (400MHz, DMSO-d6): delta 8.69 (d, J=8.4Hz, 1H), 8.44 (d, J=9.0Hz, 1H), 8.11 (d, J=8.0Hz, 1H), 8.03-7.97 (m, 2H), 7.83 (t, J=7.6Hz, 1H), 7.58 (dd, J=9.2, 2.3Hz, 1H), 4.59 (s, 3H), 4.17 (t, J=6.4Hz, 2H), 3.99 (s, 3H), 3.25-3.17 (m, 2H), 3.13 (dd, J=12.2, 6.6Hz, 2H), 3.03-2.93 (m, 2H), 2.70 (s, 3H), 2.25-2.14 (m, 2H), 1.84-1.70 (m, 2H). IR (KBr, cm-1): 3261, 3051, 2955, 2876, 1598, 1529, 1493, 1386, 1347, 1253, 1213, 1107, 1039, 977, 822, 774, 671. ESI-MS: m/z 407 [M-I]+. HRMS (ESI): m/z calcd for C24H31IN4O2 ([M-I] +) 407.1583; found 407.6453.
  • 55
  • [ 105-83-9 ]
  • [ 638-29-9 ]
  • N,N'-(methylazanediyl)bis(propan-3,1-diyl)dipentanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In methanol; at 0 - 20℃; The amine forms (Compounds 1 to 4) having no acyl groups of the compounds were prepared. 10 mL of each of the amine forms was dissolved in a solution of 200 mL of methanol and 200 mL of a 1 M sodium bicarbonate solution in a round-bottom flask. [0072] The temperature of the resulting solution was adjusted to 0 C. The acyl anhydride or acyl chloride (Compound a, b or c) having the corresponding acyl group was slowly added. 1.5 equivalents of the acyl anhydride or acyl chloride was used per equivalent of the primary and tertiary amino groups of the amine. The mixture was stirred at 0 C. for 1 h and at room temperature for additional 16-18 h. After completion of the reaction, the reaction mixture was extracted about 2-4 times with dichloromethane, followed by drying to obtain the final product. 1H NMR spectra of nBu-DETA, Val-DEEA, iBu-DEER, nBu-DAPMA, Val-DAPMA, and nBu-DIPA measured on a 300 MHz Bruker spectrometer are shown in FIGS. 3 to 8, respectively.
  • 56
  • [ 106-31-0 ]
  • [ 105-83-9 ]
  • [ 17785-26-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In methanol; at 0 - 20℃; The amine forms (Compounds 1 to 4) having no acyl groups of the compounds were prepared. 10 mL of each of the amine forms was dissolved in a solution of 200 mL of methanol and 200 mL of a 1 M sodium bicarbonate solution in a round-bottom flask. [0072] The temperature of the resulting solution was adjusted to 0 C. The acyl anhydride or acyl chloride (Compound a, b or c) having the corresponding acyl group was slowly added. 1.5 equivalents of the acyl anhydride or acyl chloride was used per equivalent of the primary and tertiary amino groups of the amine. The mixture was stirred at 0 C. for 1 h and at room temperature for additional 16-18 h. After completion of the reaction, the reaction mixture was extracted about 2-4 times with dichloromethane, followed by drying to obtain the final product. 1H NMR spectra of nBu-DETA, Val-DEEA, iBu-DEER, nBu-DAPMA, Val-DAPMA, and nBu-DIPA measured on a 300 MHz Bruker spectrometer are shown in FIGS. 3 to 8, respectively.
  • 57
  • [ 105-83-9 ]
  • [ 446-33-3 ]
  • [ 1383630-25-8 ]
YieldReaction ConditionsOperation in experiment
78.4% With sodium carbonate; at 60 - 100℃; for 12h; 5.1. Synthesis of N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)-amino]propyl}-1,3-propanediamine To 5-fluoro-2-nitrotoluene (50.0 g, 0.32 mol) was added sodium carbonate (17.1 g, 0.16 mol) at 60 C. <strong>[105-83-9]3,3'-Diamino-N-methyldipropylamine</strong> (23.7 g, 0.16 mol) was then carefully added dropwise (exothermic reaction). The resulting mixture was heated at 100 C. for 12 hours. 100 ml toluene were added to the cooled reaction mixture causing the inorganic salts to precipitate, which were filtered off. The organic phase was then concentrated down under vacuum in a rotovap to afford the product as a residue in the form of a yellow orange oil. Yield: 52.5 g (78.4%); 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.71 (m, 4H); 2.18 (s, 3H); 2.40 (m, 4H); 2.55 (s, 6H); 3.17 (m, 4H); 6.45 (s, 2H); 6.48 (d, 2H); 7.08 (br., 2*NH); 7.92 (d, 2H).
  • 58
  • [ 105-83-9 ]
  • [ 100-00-5 ]
  • [ 1383630-17-8 ]
YieldReaction ConditionsOperation in experiment
78.2% With sodium carbonate; In dimethyl sulfoxide; at 80 - 120℃; for 12h; 1.1 Synthesis of N1-methyl-N3-(4-nitrophenyl)-N1-{3-[(4-nitrophenyl)amino]propyl}-1,3-propanediamine 4-Chloronitrobenzene, 50.0 g (0.32 mol), in 100 ml dimethylsulfoxide were heated to 80 C. (clear solution). Sodium carbonate, 15.6 g (0.16 mol), was then added. N1-(3-Aminopropyl)-N1-methyl-1,3-propanediamine, 23.2 g (0.16 mol), was then added dropwise at this temperature. Following the dropwise addition the reaction mixture was then stirred for 12 h at 120 C. After cooling, water (11) was added and the aqueous phase was extracted 3 times with 200 ml ethyl acetate. The organic phase was then dried with sodium sulfate and concentrated under vacuum in a rotovap. The product remained as a residue in the form of a highly viscous oil. Yield: 48.1 g (78.2%); 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.71 (m, 4H); 2.17 (s, 3H); 2.40 (t, 4H); 3.18 (m, 4H); 6.61 (d, 4H); 7.27 (br., 2*NH); 7.98 (d, 4H).
  • 59
  • [ 105-83-9 ]
  • [ 400-94-2 ]
  • N,N'-(3,3'-(methylazanediyl)bis(propane-3,1-diyl))bis(4-fluoro-3-nitrobenzamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.61 g With triethylamine; In dichloromethane; at 20℃; for 18h; General procedure: This solutionwas slowly added to a solution of the corresponding amine andtriethylamine in CH2Cl2 at 0 C. The mixture was stirred overnightat room temperature. After removal of solvent in vacuo the crudeproduct was dispersed in concentrated Na2CO3 solution, and extracted with CH2Cl2. The combined organic phases were driedover anhydrous Na2SO4. After filtration and removal of solvent invacuo the product was purified by column chromatography toyield the corresponding amide.
  • 60
  • [ 474018-94-5 ]
  • [ 105-83-9 ]
  • 4,4'-(3,3'-(methylazanediyl)bis(propane-3,1-diyl)bis(azanediyl))bis(N,N-diethyl-3-nitrobenzamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% General procedure: The corresponding amine and triethylamine were dissolved inethanol and stirred at room temperature for 0.5-1 h. Then, a solutionof the corresponding 4-fluoro-3-nitrophenyl compound inethanol was slowly added. The mixture was stirred overnight at50-75 C. After removal of solvent in vacuo the product waspurified by column chromatography to give the corresponding4-amino-3-nitrophenyl compound.
  • 61
  • Fmoc-β-Ala-Wang resin [ No CAS ]
  • [ 105-83-9 ]
  • [ 872679-70-4 ]
  • [ 1040393-13-2 ]
  • C20H25N9O5 [ No CAS ]
  • [ 195387-29-2 ]
  • C103H129N41O20 [ No CAS ]
  • 62
  • Fmoc-β-Ala-Wang resin [ No CAS ]
  • [ 105-83-9 ]
  • [ 1040393-13-2 ]
  • C20H25N9O5 [ No CAS ]
  • [ 139338-72-0 ]
  • [ 195387-29-2 ]
  • C104H131N41O21 [ No CAS ]
  • 63
  • [ 437655-95-3 ]
  • Fmoc-β-Ala-Wang resin [ No CAS ]
  • [ 105-83-9 ]
  • [ 1040393-13-2 ]
  • C20H25N9O5 [ No CAS ]
  • [ 195387-29-2 ]
  • C106H135N41O22 [ No CAS ]
  • 64
  • 6-bromo-1-(2',4'-dichlorophenyl)-4,5-dihydro-1H-thieno[3,2-g]indazol-3-carboxylic acid [ No CAS ]
  • [ 105-83-9 ]
  • C39H33Br2Cl4N7O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% mmole of 6-bromo-1-(2?,4?-dichlorophenyl)-4,5-dihydro-1H-thieno[3,2-g]indazol-3-carboxylic acid prepared in Ex. 26aand 1.1 mmoles of 1,1?-carbonyldiimidazole (CDI) in 2.5 ml of DMF were mixed under stirring at room temperature andstirring continued for 3 hours, then 0.5 mmoles of CH3N(CH2CH2CH2NH2)2 in DMF (2 ml) were added. The reactionmixture was stirred at room temperature for 48 hours. The solvent was then removed under reduced pressure and theobtained residue was purified by flash chromatography (eluent CHCl3/CH3OH 9/1 v/v) obtaining the titled compound.Yield 38%. 1H-NMR (CDCl3) delta 1.82 (q, 4H), 2.38 (s, 3H), 2.55 (t, 4H), 2.88-3.35 (m, 8H), 3.56 (q, 4H), 7. 14 (s, 2H), 7.36(dd, 2H), 7. 47 (d, 2H), 7.63 (d, 2H).
38% 0424] 1 mmole of 6-bromo-1-(2?,4?-dichlorophenyl)-4,5-dihydro-1H-thieno[3,2-g]indazol-3-carboxylic acid prepared in Ex. 26a and 1.1 mmoles of 1,1?-carbonyldiimidazole (CDI) in 2.5 ml of DMF were mixed under stirring at room temperature and stirring continued for 3 hours, then 0.5 mmoles of CH3N(CH2CH2CH2NH2)2 in DMF (2 ml) were added. The reaction mixture was stirred at room temperature for 48 hours. The solvent was then removed under reduced pressure and the obtained residue was purified by flash chromatography (eluent CHCl3/CH3OH 9/1 v/v) obtaining the titled compound. Yield 38%. 1H-NMR (CDCl3) delta 1.82 (q, 4H), 2.38 (s, 3H), 2.55 (t, 4H), 2.88-3.35 (m, 8H), 3.56 (q, 4H), 7.14 (s, 2H), 7.36 (dd, 2H), 7.47 (d, 2H), 7.63 (d, 2H)
  • 65
  • [ 105-83-9 ]
  • [ 29548-30-9 ]
  • {3-[(3-aminopropyl)methylamino]propyl}(3,7,11-trimethyldodeca-2,6,10-trienyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With tetrakis(triphenylphosphine) palladium(0); In ethanol; at 110℃; for 1h; General procedure: To a solution of geranyl acetate (196 mg, 1 mmol) in ethanol (96%) (5 mL) is added tris(3-amino-propyl)amine (235 mg,1.25 mmol). This mixture is heated under air in an oil bath at 110 C.When the reflux is well established 46 mg of Pd(PPh3)4 (4 mol %) is quickly added in one portion. The reflux is maintained for 1 h. After cooling to room temperature, the solvent is removed under reduced pressure and the crude product is purified by column chromatography (silica gel; CH2Cl2/MeOH/NH4OH, 7:3:1) affordinga clear oil of Z-3 in 80% yield.
  • 66
  • [ 105-83-9 ]
  • [ 16409-44-2 ]
  • {3-[(3-aminopropyl)methylamino]propyl}(3,7-dimethylocta-2,6-dienyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With tetrakis(triphenylphosphine) palladium(0); In ethanol; at 110℃; for 1h; General procedure: To a solution of geranyl acetate (196 mg, 1 mmol) in ethanol (96%) (5 mL) is added tris(3-amino-propyl)amine (235 mg,1.25 mmol). This mixture is heated under air in an oil bath at 110 C.When the reflux is well established 46 mg of Pd(PPh3)4 (4 mol %) is quickly added in one portion. The reflux is maintained for 1 h. After cooling to room temperature, the solvent is removed under reduced pressure and the crude product is purified by column chromatography (silica gel; CH2Cl2/MeOH/NH4OH, 7:3:1) affordinga clear oil of Z-3 in 80% yield.
  • 67
  • [ 105-83-9 ]
  • [ 3320-86-3 ]
  • C21H27N7O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In dichloromethane; at 20℃; for 24h;Reflux; L:3,3'-diamino-N-methyl-dipropylamine (417.4 mL, 2.1 mmol) was added to 2-nitrophenyl isocyanate (0.7g, 4.2 mmol) in dichloromethane (250 mL) at room temperature under constantstirring. The mixture was reuxed for 24 hours. Solvent was evaporated. Ayellow precipitate was formed and collected by filtration. The precipitate waswashed by methanol and dried under vacuum for overnight to give the neutralpropylene-based dipodal urea receptor (L). Yield: 0.7 g , 70%. 1H NMR (500 MHz, DMSO-d6): delta 9.31 (s, 2H, Ar-NH), 8.24 (d, J = 8.4 Hz, 2H, ArH), 8.02 (d, J = 7.00 Hz, 2H, ArH), delta7.61 (t, J1 = 7.15 Hz, J2 = 7.15 Hz, 2H, ArH), 7.48 (s, 2H, Ar-NH), delta 7.09 (t, J = 8.37 Hz, 2H, ArH), delta3.11 (m, 4H, NHCH2), delta2.32 (t, J = 7.02 Hz, 4H, NCH2), delta 2.13(s, 3H, NCH3), delta 1.58 (m, 4H, CH2CH2). 13C NMR (125MHz, DMSO-d6): delta 154.61 (C=O), 137.19 (Ar-C), 136.39 (Ar-C), 135.37 (Ar-CH), 125.72 (Ar-CH),122.38 (Ar-CH), 121.71 (ArCH), 55.27 (NCH2), 42.23 (NCH3),38.08 (NHCH2), 27.64 (CH2CH2). Anal. Calcd. for C21H27N7O6: C, 53.27; H, 5.75; N, 20.71. Found: C, 53.33; H, 5.68; N, 20.65.
  • 68
  • [ 105-83-9 ]
  • 10-(5-carboxypentyl)acridine orange chloride salt [ No CAS ]
  • C53H75N9O2(2+)*2I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
250 mg Example 7 Preparation of AOAO-2 (Dye No. 7 of Table 1) (0164) Et3N (0.15 mL, 1.05 mmol) and TSTU (320 mg, 1.05 mmol) were added to a suspension of 10-(5-carboxypentyl)acridine orange chloride salt (438 mg, 1.03 mmol) in DMF (5 mL) at room temperature. The mixture was stirred at room temperature for 15 minutes, followed by the addition of Et3N (0.1 mL) and 3,3?-diamino-N-methyldipropylamine (50 mg, 0.344 mmol). After the mixture was stirred at room temperature overnight, EtOAc (20 mL) was added to precipitate the product. The crude product was re-dissolved in DMF and precipitated out again with EtOAc. The solid (250 mg) was separated by centrifugation.
  • 69
  • [ 105-83-9 ]
  • [ 1314863-61-0 ]
  • 5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5-{3-[N-methyl(3-aminopropyl)amino]propylaminocarbonyloxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-14-yl]-2-pyranone [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.4% In dichloromethane; tert-butyl methyl ether; at 20℃; for 2h; 31.8mgs (57.44.imol) of 4-nitrophenyl carbamate-3-O-bufalin was dissolved in lmL of DCMand lmL of MTBE. 46.3.iL (287.2.imol) of 3,3?-diamino-N-methyldipropylamine was addedand stirred at room temperature. After 90 minutes 4mL of MTBE was added and stirred foran additional 30 minutes. The solvent was decanted off, leaving a yellow precipitate behind.The precipitate was washed with a minimal amount of MTBE. The MTBE was decanted offand placed with the previously decanted material. The decanted solvent was rotaryevaporated off. The material was washed 4 times with lOmL of hexanes. 5mL of H20 wasadded and the precipitate was suction filtered. The precipitate was washed 3 times with 10-l5mL of H20. To the precipitate (16.Smgs) was added lmL of MeOH. The material was centrifuged with the solvent being decanted off. The decanted material was rotary evaporatedoff. 14.2 lmgs (25.48umol) of CEN-372 was obtained for a % Yield of 44.4%.TLC: 75:25DCM:EtOAc; RfCEN-372 = 0.0; Ninhydrin positive; HPLC Analysis: C18 Column:AtlantisT3; 3um; 4.6 x 150mm; Gradient: 0-2mm = 90:10 (A:B); 2-15mm = 0:100 (A:B);Flow Rate: 1 mL/min; RtCEN-372= 11.60 mm (2max = 300nm). ?H-NMR (400 MHz,DMSO-d6): oe 7.92 (d, 1H, H21), 7.51 (s, 1H, H14), 6.95 (s, 1H, H26), 6.27 (d, 1H, H20)4.78 (s, 1H, H3), 4.15 (s, 1H, H13), 3-1.1 (multiple peaks, 39H, H1,2,4-9,11,12,15-17,27-34), 0.87 (s, 3H, H18), 0.59 (s, 3H, H19). TOF-MS (ESI): MWobs = 558.39 g/mol; MWcalc. =558.84 g/mol. RJPAC Name: 5-[(1S,2S,5S,7R, bR, 11S, 14S, 15R)-5- {3-[N-Methyl(3-aminopropyl)amino]propylaminocarbonyloxy} -11 -hydroxy-2, 15-dimethyltetracyclo [8.7.0.02,7.011,15 ]heptadec- 1 4-yl] -2-pyranone
  • 70
  • [ 105-83-9 ]
  • [ 1448724-40-0 ]
  • N1-(3-aminopropyl)-N3-(2-benzyl-7-(2-methyl-2H-tetrazol-5-yl)-9H-pyrimido[4,5-b]indol-4-yl)-N1-methylpropane-1,3-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In methanol; at 140℃; for 0.5h;Microwave irradiation; A mixture of 2-benzyl-4-chloro-7-(2-methyl-2H-tetrazol-5-yl)-9H-pyrimido[4,5-b]indole prepared as described above (0.865 g, 2.302 mmol) and 3,3'-Diamino-/V-methyldipropylamine (2.60 mL, 16.1 1 mmol) in MeOH (17.4 mL) was heated 30 minutes to 140 C in a microwave oven. After cooling and evaporation of the solvent, the residue was purified by flash chromatography to give N1-(3-aminopropyl)-N3-(2-benzyl-7-(2-methyl-2H-tetrazol-5-yl)-9H- pyrimido[4,5-b]indol-4-yl)-N1-methylpropane-1 ,3-diamine (832 mg, 74% yield) as a yellow solid; 1H NMR (400 MHz, DMSO-d6) delta ppm 1.52 (quin, J=6.85 Hz, 2 H) 1.80 (quin, J=6.85 Hz, 2 H) 2.18 (s, 3 H) 2.36 (t, J=7.24 Hz, 2 H) 2.41 (t, J=6.65 Hz, 2 H) 2.53 - 2.61 (m, 2 H) 3.64 (q, J=6.52 Hz, 2 H) 4.04 (s, 2 H) 4.43 (s, 3 H) 7.14 - 7.23 (m, 1 H) 7.28 (t, J=7.43 Hz, 2 H) 7.38 (d, J=7.43 Hz, 2 H) 7.49 (t, J=5.09 Hz, 1 H) 7.91 (d, J=8.22 Hz, 1 H) 8.08 (s, 1 H) 8.32 (d, J=8.22 Hz, 1 H); HPLC 99.4% at 254 nm, RT 1.608 minutes; HRMS m/z 485.2884 (M+H)+.
  • 71
  • [ 12093-10-6 ]
  • [ 105-83-9 ]
  • N-ferrocenyl-N-(3-aminopropyl)-N-methylpropane-1,3-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% General procedure: A mixture of ferrocene carboxaldehyde(9.3 mmol, 2 g, 1 eq.) and the appropriate primarydiamine (46.5 mmol, 5 eq.) was stirred in anhydrousMeOH (50 ml) for 4 h at room temperature. An excess ofsodium borohydride, NaBH4 (93 mmol, 3.5 g, 10 eq.), wasadded, and stirring was continued for an additional 2 h atroom temperature (Scheme 1). Afterward, the reactionmixture was acidified with HCl (1 M, 50 ml), diluted withwater (50 ml) and extracted with EtOAc (2 9 50 ml) toremove any unreacted ferrocene carboxaldehyde. Theaqueous layer was basified to pH 10 with a solution ofsaturated NaHCO3 and extracted with EtOAc (3 9 50 ml).The combined organic layers were dried over MgSO4, andthe solvent was removed in vacuo. The residue was subjectedto column chromatography on silica gel, elutingsuccessively with DCM:MeOH (9:1, v/v) and then withCH2Cl2:MeOH:NH4OH (25 %), (4:1:0.1, v/v/v) to affordthe pure compounds 1-8 in high yields.
  • 72
  • [ 105-83-9 ]
  • [ 439147-09-8 ]
  • 1-{3-[N-(3-aminopropyl)-N-methylamino]propylamino}-4-methyl-9(10H)-acridone trihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% Preparation of derivative 2h: l-{3-[N-(3- Aminopropyl)-N-methylamino]propylamino}-4-methyl-9(10H)-acridone 'x3HCl. A mixture of 1- chloro-4-methyl-9(10H)-acridone (lb) (2.0 g, 0.0082 mol) and 3,3-diamino-N-methyldipropylamine (10 ml) were reacted using a microwave reactor. The synthesis parameters were: the efficiency of the microwave reactor was P=25%, tmin=120C, tmax=130C, the conduct time was lh. After this time, the mixture was cooled to room temperature and then poured into water (100 ml) and extracted with chloroform. The product was purified by column chromatography. The initial eluent was CHC13/MeOH (4:1 v/v) and then CHC13/MeOH/NH3 (3: 1 :0.01, v/v). Fractions containing the desired product were evaporated, and then it was dissolved in methanol (10 ml) and acidified with HC1/diethyl ether. After adding acetone the desired product was obtained. Yield 47%.
  • 73
  • [ 105-83-9 ]
  • [ 99009-49-1 ]
  • 1-{3-[N-(3-aminopropyl)-N-methylamino]propylamino}-7-hydroxy-4-nitro-9(10H)-acridone dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% Synthesis of derivative 2a: l-{ 3-fN- ( 3-Aminopropyl)-N-methylamino ]propylamino}- 7-hydroxy-4- nitro-9(10H)-acridone x2HCl. A mixture of l -chloro-7-hydroxy-4-nitro-9(10H)-acridone (la) (1.45 g, 0.005 mol), and 3,3-diamino-N-methyldipropylamine 2.90 g (0.02 mol) in DMSO (25 ml) was stirred at room temperature for 2.5 h. After this time, water was added (-200 ml) and the reaction mixture was stirred for 0.5 h. The precipitate was collected by filtration. Next, it was transferred into water, acidified with a dilute hydrochloric acid and stirred for 0.5 h. Undissolved material was filtered off, and the solution was evaporated to a small volume. The product was precipitated out using acetone (-100 ml), and then was filtered off to give 1.2 g (51 %).
  • 74
  • [ 105-83-9 ]
  • [ 20621-51-6 ]
  • 1-{3-[N-(3-aminopropyl)-N-methylamino]propylamino}-4-nitro-9(10H)-acridone dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Preparation of derivative 2i: l-{3-[N- (3-Aminopropyl)-N-methylamino]propylamino}-4-nitro-9(10H)-acridone x2HCl. A mixture of 1- chloro-4-nitro-9(10H)-acridone (lc) (0.01 mol), 3,3-diamino-N-methyldipropylamine (0.04 mol) in DMSO (50 ml) was stirred at room temperature for 3 h. After this time, water was added (-200 ml) and then stirred for 10 min. The precipitate was collected by filtration and suspended into water (-100 ml) and then acidified with a dilute hydrochloric acid and stirred again for 15 min. The insoluble precipitate was filtered off, and the filtrate was evaporated to a smaller volume. The product was precipitated out using acetone (-100 ml), and then was filtered off. Yield 81%.
  • 75
  • [ 105-83-9 ]
  • [ 118-92-3 ]
  • N,N'-[(methylazanediyl)bis(propane-3,1-diyl)]bis(2-aminobenzamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.6% General procedure: Compound 1 (10 mmol) and CDI (11 mmol) in DMF (100 mL) were stirred for 1 h at roomtemperature. Then the appropriate polyamine (a-d) (6 mmol) was added and stirring was continuedfor additional 2 h. At the end of the reaction, the mixture was filtered. The solvent was removed invacuum. 20 mL of H2O was added to the residue (compounds 3a,b) and left for 24 h at 5 C. Then thesolid was filtered off, washed with H2O and crystallized from DMF/H2O. The residue was purified bycolumn chromatography over silica gel (CHCl3/MeOH, 100:1-0:1, v/v) to give compounds 3c,d.
  • 76
  • [ 105-83-9 ]
  • [ 93-09-4 ]
  • N,N'-[(methylazanediyl)bis(propane-3,1-diyl)]bis(2-naphthamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
54.6% General procedure: A mixture of acid 10-13 (10 mmol) and CDI (10 mmol) in acetonitrile (100 mL) or DMF (100 mL)was stirred for 1 h at room temperature. Then the appropriate polyamine (a-d) (6 mmol) was addedand stirring was continued for additional 2 h, then the mixture was filtered. The solvent was removedunder reduced pressure and 20 mL of H2O was added to the residue and left for 24 h at 5 C(for compounds 11a-d, 13a-d, 14a-d. Then the solid was filtered off, washed with H2O and crystallizedfrom DMF/H2O. In case of compounds 12a-d the residues were purified by column chromatographyover silica gel (CHCl3/MeOH, 100:1, 10:1, v/v).
  • 77
  • [ 93-10-7 ]
  • [ 105-83-9 ]
  • N,N'-[(methylazanediyl)bis(propane-3,1-diyl)]bis(quinoline-2-carboxamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.9% General procedure: A mixture of acid 10-13 (10 mmol) and CDI (10 mmol) in acetonitrile (100 mL) or DMF (100 mL)was stirred for 1 h at room temperature. Then the appropriate polyamine (a-d) (6 mmol) was addedand stirring was continued for additional 2 h, then the mixture was filtered. The solvent was removedunder reduced pressure and 20 mL of H2O was added to the residue and left for 24 h at 5 C(for compounds 11a-d, 13a-d, 14a-d. Then the solid was filtered off, washed with H2O and crystallizedfrom DMF/H2O. In case of compounds 12a-d the residues were purified by column chromatographyover silica gel (CHCl3/MeOH, 100:1, 10:1, v/v).
  • 78
  • [ 105-83-9 ]
  • [ 452347-16-9 ]
  • N,N'-[(methylazanediyl)bis(propane-3,1-diyl)]bis(2-oxo-2H-chromene-3-carboxamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
56.8% General procedure: A mixture of acid 10-13 (10 mmol) and CDI (10 mmol) in acetonitrile (100 mL) or DMF (100 mL)was stirred for 1 h at room temperature. Then the appropriate polyamine (a-d) (6 mmol) was addedand stirring was continued for additional 2 h, then the mixture was filtered. The solvent was removedunder reduced pressure and 20 mL of H2O was added to the residue and left for 24 h at 5 C(for compounds 11a-d, 13a-d, 14a-d. Then the solid was filtered off, washed with H2O and crystallizedfrom DMF/H2O. In case of compounds 12a-d the residues were purified by column chromatographyover silica gel (CHCl3/MeOH, 100:1, 10:1, v/v).
  • 79
  • [ 1477-50-5 ]
  • [ 105-83-9 ]
  • N,N'-[(methylazanediyl)bis(propane-3,1-diyl)]bis(1H-indole-2-carboxamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% General procedure: A mixture of acid 10-13 (10 mmol) and CDI (10 mmol) in acetonitrile (100 mL) or DMF (100 mL)was stirred for 1 h at room temperature. Then the appropriate polyamine (a-d) (6 mmol) was addedand stirring was continued for additional 2 h, then the mixture was filtered. The solvent was removedunder reduced pressure and 20 mL of H2O was added to the residue and left for 24 h at 5 C(for compounds 11a-d, 13a-d, 14a-d. Then the solid was filtered off, washed with H2O and crystallizedfrom DMF/H2O. In case of compounds 12a-d the residues were purified by column chromatographyover silica gel (CHCl3/MeOH, 100:1, 10:1, v/v).
  • 80
  • [ 571-60-8 ]
  • [ 105-83-9 ]
  • 2,2'-(((methylazanediyl)bis(propane-3,1-diyl))bis(azanediyl))bis(naphthalene-1,4-dione) [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With cerium(III) chloride heptahydrate; triethylamine; In ethanol; at 20℃; for 4h; General procedure: The following procedure is the generalized synthetic procedure used for the synthesis of 2-amino-substituted-1,4-naphthoquinone derivatives. To the mixture of 1,4-dihydroxy naphthalene (100 mg, 0.62 mmol), amine (0.75 mmol), and CeCl3*7H2O (20 mg, 0.062 mmol) in 10 mL ethanol, TEA (1.25 mmol) was added at room temperature. The reaction mixture was stirred for 4 h at room temperature. After the reaction was confirmed as completed by TLC (DCM: MeOH = 19: 1), 10 mL cold water was added to the reaction solution. The resulting precipitate was filtered and washed with 20 mL EtOH. The desired 1,4-naphthoquinone derivatives were obtained as a solid compound.
18.5% With cerium(III) chloride heptahydrate; triethylamine; In ethanol; at 20℃; for 6h; 1,4-Dihydroxy naphthalene (200 mg, 1.248 mmol) was dissolved in EtOH (10 mL) and then CeCl3 7H2O (20 mg, 0.062 mmol), N, N- 1.25 mmol) were slowly added dropwise in this order and reacted at room temperature. After 6 hours, the reaction was confirmed to be complete (TLC with DCM: MeOH = 19: 1), followed by quenching with water and DCM, Dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (developing solvent HEX - & gt; DCM: MeOH = 19: 1) to obtain the target compound 6 (yield: 18.5%).
  • 81
  • [ 1129-30-2 ]
  • nickel(II) perchlorate hexahydrate [ No CAS ]
  • [ 105-83-9 ]
  • Ni(Me3[14]pydieneN4) perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Ca. 65% To an ethanol solution (60 mL) of 2,6-Diacetylpyridine(3.26 g, 0.02 mol) was added Nickel(II) perchlate hexahydrate(7.3 g, 0.02 mol). The mixture solution was heated toabout 65 C and 2.9 g 0.02 mol) of 3,3?-diamino-(N-methyl)dipropylamine was added, and the solution was refluxed forabout 6 h, after which the solution was condensed on a rotaryevaporator to reduce the volume of the solution to about 15mL. After filtering the remaining solution to remove the tinyinsoluble materials, excess of ether was added to precipitatethe target compound. The product was collected by filtration,washed with ether and dried in air. Yield: about 65%. Anal.Calcd. for C16H24Cl2N4NiO8: C, 36.26; H, 4.57; N, 10.57%.Found: C, 36.21; H, 4.51; N, 10.68%.
  • 82
  • [ 105-83-9 ]
  • [ 292638-85-8 ]
  • C23H43N3O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.4% In methanol; at 20 - 30℃; for 24h;Cooling with ice; Inert atmosphere; Darkness; The reaction device was built, including a water bath, a three-necked flask, a spherical condenser, a drying tube, and a nitrogen supply device.First set the device in an ice water bath and pass nitrogen for 5 minutes.Take 2.9 g (20 mmol) of 3,3-diamino-N-methyldipropylamine and dissolve in 5 ml of anhydrous methanol.Add a three-necked flask connected to a spherical condenser and a drying tube, and then pass nitrogen for 20 minutes.Then, 13.76 g (160 mmol) of methyl acrylate was weighed and added to the three-necked bottle at a rate of 3/s in the dark.After the completion of the dropwise addition, the system was naturally returned to room temperature, and then set at 30 C for 24 hours. After the reaction is over,The methanol was removed by rotary distillation, and methyl acrylate was repeatedly distilled by adding anhydrous methanol to circulate for 5 times or more.Finally, 8.65 g of a pale yellow micro-viscous liquid, Compound I, was obtained in a yield of 88.4%.
  • 83
  • [ 105-83-9 ]
  • 2-hexyldecyl 6-bromohexanoate [ No CAS ]
  • C95H187N3O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With potassium carbonate; caesium carbonate; sodium iodide; In tetrahydrofuran; at 70℃; for 144h; A mixture of N,N-di(3-aminopropyl)methylamine (0.925 mmol, 134 mg), 9-1 (1.478 g, 3.52 mmol; prepared from 6-bromohexanoic acid and 2-hexyl-l- decanol), potassium carbonate (3.52 mmol, 486 mg), cesium carbonate (0.56 mmol, 181 mg,), sodium iodide (5 mg) and anhydrous THF (15 mL) in a pressure flask was heated at 70 C for 6 days. The solvent was evaporated under reduced pressure and the residue was taken in hexanes/ethyl acetate (90: 10) and washed with water and brine. The organic layer was separated and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield a light yellow oil (1.4 g). The residue was taken up in hexanes and was filtered through a thin pad of silica gel. The pad was washed with a mixture of Hexane-EtO Ac (93:3) to yield the unreacted 9-1 (197 mg colorless oil). The pad was further washed with a mixture of hexane/EtO Ac/Et3N (80:20: 1). The washing was concentrated to dryness, affording the desired product as a slightly yellow oil (460 mg). The oil was further purified by column chromatography on silica gel (MeOH in chloroform, from 0% to 5%). This gave the desired product as a colorless oil (131 mg, 0.09 mmol, 10%). 'HNMR (400 MHz, CDC13) delta: 3.97 (d, 5.8 Hz, 8H), 2.66-2.28 (m, 24H), 2.21 (s, 3H), 1.69-1.54 (m, 16H), 1.49-1.39 (m, 8H), 1.37- 1.15 (m, 104H), 0.89 (t-like, 6.8 Hz, 24H).
  • 84
  • [ 105-83-9 ]
  • [ 24782-64-7 ]
  • C21H25ClN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of 68 6 (100mg, 0.42mmol) were added 69 SOCl2 (0.65mL, 8.6mmol), 70 DMF (3.2 muL), and then the mixture was stirred at 70C for 4h. The crude was then co-evaporated three times with CH2Cl2. The dried residue was dissolved with 71 CH2Cl2 (6 mL) and to the solution was added a solution of 75 3,3?-Diamino-N-methyldipropylamine (0.7mL) in CH2Cl2 (5mL). After stirring the reaction mixture at r.t. for 1h, to the solution mixture was added 76 acetic anhydride (1.7mL), then the mixture was further stirred for 1h. The reaction mixture was then concentrated under reduced pressure and purified by column chromatography (CHCl3: MeOH=9:1?5:1?3:1?2:1 (containing 0.1% 72 TEA)) to afford 16 8 as a dark orange oil (52mg, 0.12mmol, 29%).
  • 86
  • [ 105-83-9 ]
  • [ 13402-02-3 ]
  • C83H163N3O8 [ No CAS ]
Reference: [1]Small,2019,vol. 15
  • 88
  • [ 105-83-9 ]
  • [ 439147-09-8 ]
  • [ 2470768-52-4 ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 3,3'-Diamino-N-methyldipropylamine; 1-chloro-4-methylacridin-9(10H)-one at 150℃; for 24h; Stage #2: With hydrogenchloride In methanol; diethyl ether Preparation of derivative 2h: 1-{3-[N-(3-Aminopropyl)-N-methylamino]propylamino}-4-methylacridin-9(10H)-one x2HCl. Amixture of 1-chloro-4-methylacridin-9(10H)-one (1b) (1.5 g,0.0062 mol) and 3,3'-diamino-N-methyldipropylamine (10 ml) wasstirred and heated at 150 °C for 24 h. After this time, the mixturewas cooled to room temperature and then poured into water(100 ml) and then stirred for 0.5 h. The precipitate was collected by filtration, washed with water and dried. The product was purifiedby silica gel column chromatography using the initial eluent CHCl3/MeOH at a ratio of (4:1 v/v) and then was CHCl3/MeOH/NH3(3:1:0.01, v/v). The main fraction after evaporated was crystallizedfrom chloroform-hexane. The crystals were dissolved in methanol(10 ml) and acidified with HCl/diethyl ether. After adding of acetone(~100 ml) the desired product was obtained. The yield was 50%.
  • 89
  • [ 105-83-9 ]
  • [ 128113-28-0 ]
  • [ 2470768-93-3 ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 3,3'-Diamino-N-methyldipropylamine; 5-chloro-8-hydroxy-6H-ν-triazolo<4,5,1-de>acridin-6-one In N,N-dimethyl acetamide at 60℃; for 4h; Stage #2: With hydrogenchloride In methanol; diethyl ether Preparation of derivative 7a: 1-(Aminopropyl)-4[N-5-(8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]-acridin-6-on)-3-aminopropyl]piperazinex4HCl General procedure: A mixture of 1,4-bis-(3-amionopropyl)piperazine(2.7 g, 0.0135 mol), 6a (1.16 g, 0.0045 mol) in DMA (10 ml) [6], washeated at 60 °C for 4 h. After this time, methanolwas added and thereaction mixture was left overnight in the refrigerator. The precipitatewas filtered off and then dissolved in chloroform, acidifiedwith HCl/diethyl ether and was precipitated out with diethyl ether.The product was crystallized from methanol/acetone. The yieldwas65%.
  • 90
  • [ 50-00-0 ]
  • [ 105-83-9 ]
  • [ CAS Unavailable ]
  • [ 2484716-23-4 ]
YieldReaction ConditionsOperation in experiment
332.3 g Stage #1: 3,3'-Diamino-N-methyldipropylamine; acetone With platinum on carbon; hydrogen In tetrahydrofuran; water at 120℃; for 5.5h; Stage #2: formaldehyd With hydrogen In tetrahydrofuran; water at 130℃; for 6h; 9 EXAMPLE 9 (Inventive) (0231) This example describes the synthesis of N,N”-diisopropyl-N,N’,N”- trimethyldipropylenetriamine as a catalyst of this invention. Procedure: A 2 liter stainless steel reactor was charged with 208 g N,N-bis(3- aminopropyl)-N-methylamine, 204 g of tetrahydrofuran and 7.9 g of 5% Pt/C catalyst (50 % suspension in water) and the reactor was purged with nitrogen. The reactor temperature was increased to 120°C followed by an increase in hydrogen pressure to 800 psig. Acetone (213 ml) was fed into the reactor over a period of 3.5 hours followed by keeping the temperature at 120°C for about 2 hours. The reactor temperature was then increased to 130°C before feeding 247 ml of formalin solution over a period of ~4 hours until the hydrogen consumption was completed. The reactor was kept at temperature for an additional 2 hours and then cooled to room temperature and the contents filtered to remove the Pt/C catalyst. The crude filtered product was transferred to a rotary evaporator yielding 332.3 g of N,N”-diisopropyl-N,N’N”- trimethyldipropylenetriamine with a 97 % purity based on GC analysis. (0233) N,N”-diisopropyl-N,N’,N”-trimethyldipropylenetriamine is
  • 91
  • [ 35654-56-9 ]
  • [ 105-83-9 ]
  • [ 2611375-44-9 ]
YieldReaction ConditionsOperation in experiment
41% With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 1,4-dioxane at 70℃; for 15h; 147.1 Step 1: To a stirring solution of 4-chloro-6,7-dimethoxyquinoline (200 mg, 0.89 mmol) in dioxane (9 ml), -aminopropyty-N^methylpropane-l, 3-diamine (260 mg, 1.79 mmol), palladium(II) acetate (10 mg, 0.04 mmol), 2,2'-bis(diphenylphosphino)-l,T- binaphthalene (55 mg, 0.09 mmol), sodium tert-butoxide (257 mg, 2.67 mmol) were added. The resulting mixture was purged with nitrogen for 10 minutes then heated to 70 °C for 15 hours. The reaction was cooled down to room temperature, diluted with methylene chloride and water, filtered through celite, extracted with methylene chloride three times. The organic layer was combined, dried over sodium sulfate, and concentrated by reduced pressure. The crude product was purified through HPLC (0-50 % acetonitrile in water) to give N1-^- aminopropyl)-N3-(6,7-dimethoxyquinolin-4-yl)-N1-methylpropane-l, 3-diamine as yellow solid (121 mg, 41%).1H NMR (CDCl3) d 8.28 (d, J= 5.4 Hz, 1H), 7.22 (s, 2H), 6.96 (s,1H), 6.20 (d, J= 5.5 Hz, 1H), 3.86 (d, J= 6.7 Hz, 6H), 3.26 (t, J= 5.3 Hz, 2H), 2.61 (t, J= 6.8 Hz, 2H), 2.55 - 2.44 (m, 2H), 2.44 - 2.33 (m, 2H), 2.25 (s, 3H), 2.08 (d, J= 10.0 Hz,2H), 1.92 - 1.71 (m, 2H), 1.55 (dd, J= 8.2, 6.4 Hz, 2H). MS m/z (M+H) = 333.60.
  • 92
  • [ 98591-57-2 ]
  • [ 105-83-9 ]
  • [ 947699-89-0 ]
YieldReaction ConditionsOperation in experiment
50% With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 1,4-dioxane at 70℃; for 15h; 151 Example 151: Synthesis of N1-(3-aminopropyl)-N3-(7-chloroquinolin-4-yl)-N1- methylpropane-1, 3-diamine: To a solution of 7-chloro-4-iodoquinoline (200 mg, 0.69 mmol) in dioxane (7 ml), N1-(3-aminopropyl)-N1-methylpropane-l, 3-diamine (200 mg, 1.38 mmol), palladium(II) acetate (8 mg, 0.03 mmol), 2, 2'-bis(diphenylphosphino)- 1,1 '-binaphthalene (43 mg, 0.07 mmol), sodium tert-butoxide (199 mg, 2.07 mmol) were added. The resulting mixture was purged with nitrogen for 10 minutes then heated to 70 °C for 15 hours. The reaction was cooled down to room temperature diluted with methylene chloride and water, filtered through celite, extracted with methylene chloride three times. The organic layer was combined, dried over sodium sulfate, and concentrated by reduced pressure. The crude product was purified by HPLC (0-50 % acetonitrile in water) to give N1-(3-aminopropyl)-N3- (7-chloroquinolin-4-yl)-N1-methylpropane-l, 3-diamine as yellow solid (105 mg, 50 %).1H NMR (CDCl3) d 8.44 (d, J= 5.4 Hz, 1H), 7.87 (d, J= 2.1 Hz, 1H), 7.66 (d, J= 8.9 Hz, 1H), 7.36 - 7.04 (m, 1H), 6.26 (d, J= 5.4 Hz, 1H), 3.33 (t, J= 6.0 Hz, 2H), 2.75 (t, J= 6.8 Hz, 2H), 2.66 - 2.41 (m, 6H), 2.32 (s, 3H), 2.07 - 1.78 (m, 2H), 1.68 (p, J= 6.9 Hz, 2H). MS m/z (M+H) = 307.70.
  • 93
  • [ 4701-17-1 ]
  • [ 105-83-9 ]
  • [ 2694864-99-6 ]
YieldReaction ConditionsOperation in experiment
77% In tetrahydrofuran at 20℃; for 3h; 2.3. Synthesis of 3,3 -di-((( E )-(5-bromothiophen-2- yl)methylene)amino)- N -methylpropylamine (3a) The target compound was synthesized following conventional condensation reactions. A solution of 757 mg (5.0 mmol) of 3,3 -diamino- N -methyldipropylamine in 10 mL of THF was added portion-wise to a stirred solution of 2011 mg (10.0 mmol) of 5- bromo-2-thiophenecarboxaldehyde in 10 mL of THF in 50-milliliter round-bottomed flask. The mixture was stirred at room temper- ature for 3 h and then the volatile was removed under reduced pressure. The residue was purified by column chromatography us- ing ethyl acetate and hexane as eluent solvent, yielding green- colored oily-like product in 77% (1.90 g). 1 H-NMR (600 MHz, CDCl 3 ): = 8.19 (t, J = 1.3 Hz, 2H, H C = N), 6.98 (d, J = 3.8 Hz, 2H, C H -thienyl), 6.97 (d, J = 3.9 Hz, 2H, C H -thienyl), 3.53 (td, J = 6.9, 1.3 Hz, 4H, C H 2 NCH 3 ), 2.38 (t, J = 6.9, 4H, C H 2 N = CH), 2.20 (s, 3H, NC H 3 ), 1.80 (quint, J = 6.9 Hz, 4H, CH 2 C H 2 CH 2 ) ppm. 13 C-NMR (151 MHz, CDCl 3 ): = 153.63 (s, 2C, H C = N), 144.22 (s, 2C, C -thienyl), 130.34 (s, 2C, C H-thienyl), 130.21 (s, 2C, C H-thienyl), 116.74 (s, 2C, C Br), 59.05 (s, 2C, C H 2 NCH 3 ), 55.19 (s, 2C, C H 2 N = CH), 42.17 (s, 1C, N C H 3 ), 28.26 (s, 2C, CH 2 C H 2 CH 2 ) ppm. LC-MS (ESI), m / z : 4 93.9 [M] + , 4 91.9 [M] + , 4 89.9 [M] + , 318.0 [M] + , 288.2 [M] + , 244.2 [M] + , 102.1 [M] + and 74.1 [M] + . Selected IR frequencies (cm -1 ): 3095 v (C-Hthienylic) , 2910 v (C-Haliphatic) , 1630 v (C = N) , 1621 v (C = C) cm -1 . Anal. Calcd. for C 17 H 21 Br 2 N 3 S 2 : C, 41.56; H, 4.31; N, 8.55. Found: C, 41.86; H, 4.22; N, 8.62. UV/Vis. Abs. in EtOH, max = 203 and 292 nm.
  • 94
  • [ 4521-33-9 ]
  • [ 105-83-9 ]
  • [ 2694865-00-2 ]
YieldReaction ConditionsOperation in experiment
79% In tetrahydrofuran at 20℃; for 3h; 2.4. Synthesis of 3,3 -di-((( E )-(5-nitrothiophen-2- yl)methylene)amino)- N -methylpropylamine (3b) In a similar manner to the abovementioned synthesis, a solution of 757 mg (5.0 mmol) of 3,3 -diamino- N -methyldipropylamine in 10 mL of THF was added portion-wise to a stirred solution of 1604 mg (10.0 mmol) of 5-nitro-2-thiophenecarboxaldehyde in 10 mL of THF in 50-milliliter round-bottomed flask. The mixture was stirred at room temperature for 3 h and then the volatile was re- moved under reduced pressure. The residue was purified by col- umn chromatography using ethyl acetate and hexane as eluent solvent, giving black-colored sticky solid product in 79% (1.67 g). 1 H-NMR (600 MHz, CDCl 3 ): = 8.31 (t, J = 1.3 Hz, 2H, H C = N), 7.82 (d, J = 4.2 Hz, 2H, C H -thienyl), 7.17 (d, J = 4.2 Hz, 2H, C H - thienyl), 3.64 (td, J = 6.8, 1.1 Hz, 4H, C H 2 NCH 3 ), 2.49 (t, J = 6.8 Hz, 4H, C H 2 N = CH), 2.28 (s, 3H, NC H 3 ), 1.87 (quint, J = 6.8 Hz, 4H, CH 2 C H 2 CH 2 ) ppm. 13 C-NMR (151 MHz, CDCl 3 ): = 153.50 (s, 2C, H C = N), 152.97 (s, 2C, C NO 2 ), 148.67 (s, 2C, C -thienyl), 128.56 (s, 2C, C H-thienyl), 128.06 (s, 2C, C H-thienyl), 58.96 (s, 2C, C H 2 NCH 3 ), 55.00 (s, 2C, C H 2 N = CH), 41.95 (s, 1C, N C H 3 ), 27.86 (s, 2C, CH 2 C H 2 CH 2 ) ppm. LC-MS (ESI), m / z : 331.1 [M-2NO 2 ] + , 288.2 [M] + , 244.2 [M] + , 102.1 [M] + and 74.1 [M] + . Selected FTIR frequen- cies (cm -1 ): 3101 v (C-Hthienylic) , 2938 v (C-Haliphatic) , 1628 v (C = N) , 1620 v (C = C) , 1360 v (N = O) cm -1 . Anal. Calcd. for C 17 H 21 N 5 O 4 S 2 : C, 48.21; H, 5.00; N, 16.54. Found: C, 47.98; H, 4.69; N, 16.46. UV/Vis. Abs. in EtOH, max = 200 and 333 nm.
  • 95
  • [ 4286-55-9 ]
  • [ 105-83-9 ]
  • [ 27610-92-0 ]
  • C79H155N3O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-6-hexanol; 2-butyloctanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16.5h; Stage #2: 3,3'-Diamino-N-methyldipropylamine With potassium carbonate In ethanol at 110℃; 15 Example 15 Synthesis of Compound 27 Dissolve 2-butyloctanoic acid (1.5eq) in appropriate amount of dichloromethane, add DMAP (0.5eq), EDC (1.5eq) to activate the carboxyl group, add 6-bromohexanol (1.0eq) after 30min, and stir overnight at room temperature . TLC confirmed that the 6-bromohexanol reaction was complete, extracted with saturated sodium bicarbonate solution several times, added anhydrous sodium sulfate for drying, filtered, and concentrated to obtain the brominated intermediate product.The brominated intermediate product (4.8eq) was added to an appropriate amount of ethanol, 2mL of N,N-bis(3-aminopropyl)methylamine (1.0eq) was dissolved in an appropriate amount of ethanol, and potassium carbonate (4.8eq) was added , The reaction was stirred overnight at 110°C under reflux. TLC confirmed that the reaction of N,N-bis(3-aminopropyl)methylamine was complete, used methanol and dichloromethane to pass through a chromatographic column, and concentrated to obtain compound 27.
  • 96
  • [ 105-83-9 ]
  • [ 55362-80-6 ]
  • [ 27610-92-0 ]
  • C91H179N3O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 9-bromononan-1-ol; 2-butyloctanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16.5h; Stage #2: 3,3'-Diamino-N-methyldipropylamine With potassium carbonate In ethanol at 110℃; 12 Example 12 Synthesis of Compound 21 Dissolve 2-butyloctanoic acid (1.5eq) in appropriate amount of dichloromethane, add DMAP (0.5eq), EDC (1.5eq) to activate the carboxyl group, add 9-bromo-1-nonanol (1.0eq) after 30min, Stir at room temperature for 16h. TLC confirmed that the reaction of 9-bromo-1-nonanol was complete, extracted with saturated sodium bicarbonate solution several times, dried with anhydrous sodium sulfate, filtered, and concentrated to obtain the brominated intermediate product.Add the brominated intermediate product (4.8eq) to an appropriate amount of ethanol,N,N-bis(3-aminopropyl)methylamine (1.0eq) was dissolved in an appropriate amount of ethanol, potassium carbonate (4.8eq) was added, and the mixture was stirred and refluxed overnight at 110°C. TLC confirmed that the reaction of N,N-bis(3-aminopropyl)methylamine was complete, used methanol and dichloromethane to pass through a chromatographic column, and concentrated to obtain compound 21.
  • 97
  • [ 105-83-9 ]
  • [ 2478-10-6 ]
  • [ 27610-92-0 ]
  • C83H155N3O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-butyloctanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 4-hydroxybutyl acrylate In dichloromethane at 20℃; Stage #3: 3,3'-Diamino-N-methyldipropylamine With potassium carbonate In methanol 18 Example 18 Synthesis of Compound 33 Dissolve 2-butyloctanoic acid (1.5eq) in an appropriate amount of dichloromethane, Stir, add EDC (1.5eq), DMAP (0.5) and triethylamine (1eq),Stir at room temperature for 0.5h,Add 4-hydroxybutyl acrylate (1.0eq) and react at room temperature overnight. TLC confirmed the complete reaction of the raw materials, added acetic acid to adjust pH=6-7, extracted several times, and obtained colorless and transparent liquid by column chromatography.Dissolve the colorless and transparent liquid (4.8eq) obtained above in an appropriate amount of methanol, add potassium carbonate (4.8eq), and then add N,N-bis(3-aminopropyl)methylamine (1.0eq) and stir at 75°C Overnight; TLC monitors the complete reaction of the raw materials, concentrate the reaction solution, use methanol and dichloromethane to pass through a chromatographic column, and concentrate to obtain compound 33.
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