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Chemical Structure| 865169-07-9
Chemical Structure| 865169-07-9
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Product Details of [ 865169-07-9 ]

CAS No. :865169-07-9 MDL No. :MFCD34165569
Formula : C20H12N4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KMTSPRCZFZYYKS-UHFFFAOYSA-N
M.W : 340.33 Pubchem ID :46865048
Synonyms :

Safety of [ 865169-07-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 865169-07-9 ]

* 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 [ 865169-07-9 ]

[ 865169-07-9 ] Synthesis Path-Downstream   1~50

  • 1
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 15746-57-3 ]
  • [ 865169-07-9 ]
  • bis(2,2'-bipyridine)(2-(4-carboxyphenyl)imidazo[4,5-f][1,10]phenanthroline)ruthenium(II) hexafluorophosphate [ No CAS ]
  • 2
  • [ 27318-90-7 ]
  • [ 619-66-9 ]
  • [ 865169-07-9 ]
YieldReaction ConditionsOperation in experiment
75% With ammonium acetate; glacial acetic acid; for 4h;Reflux; Inert atmosphere; A mixture of ammonium acetate (3.5g, 45mmol), 4-carboxybenzaldehyde (150mg, 1mmol) 1,10-phenanthroline-5,6-dione (210mg, 1mmol) and glacial acetic acid (40mL) was refluxed for 4h under argon atmosphere. After cooled to room temperature, diluted with amount of water (30mL) and neutralized with concentrated aqueous ammonia. The resulting orange solution was removed to give an orange powder, which was washed with amounts of water and dried under vacuum. Yield: 255mg, 75%. MALDI-TOF-MS (DMSO, m/z): 341.1 ([M+1]+).
67.1% With ammonium acetate; glacial acetic acid; at 110℃; for 4h; General procedure: A solution containing 1,10-phenanthroline-5,6-dione (1.6 mmol, 347 mg), substituted benzaldehyde (1.6 mmol), 20 ml of HAc and NH4Ac (33 mmol, 2.53 g), was heated at 110 C under reflux for 4 h. Then, 20 ml of water was added and the pH value was adjusted to 7.0 at room temperature. The solution was filtered and dried in vacuum to obtain a yellow precipitate. The product was purified in a silica gel column by using ethanol as eluent. 1a: yield 78.4%; mp. 217-219 C, ESI-MS (in MeOH): m/z: 219.1, ([M + H]), 438.1,([M + 2H]2+). 2a: yield 79.5%; mp. 226-228 C, ESI-MS (in MeOH): m/z: 339.15, ([M + H]+), 678.1, ([M + 2H]2+). 3a: yield 64.4%; mp. 262-265 C, ESI-MS (in MeOH): m/z: 325.1, ([M + H]+), 650.3, ([M + 2H]2+). 4a: yield 75.7%; mp. 234-236 C, ESI-MS (in MeOH): m/z: 311.1, ([M + H]+). 5a: yield 67.1%; mp. 232-235 C, ESI-MS (in MeOH): m/z: 339.1, ([M + H]+). 6a: yield 67.7%; mp. 280-283 C, ESI-MS (in MeOH): m/z: 363.1, ([M + H]+), 726.1, ([M + 2H]2+). 7a: yield 63.4%; mp. 269-273 C, ESI-MS (in MeOH): m/z: 375.2, ([M + H]+), 750, ([M 2H]2+), 772.8, ([M + H + Na]2+).
63% With ammonium acetate; glacial acetic acid; for 2h;Reflux; General procedure: o-TFPIP was prepared by a similar method to that reported [31], and with some modification. In general,a solution of 1,10-phenanthraquinone (525 mg, 2.5 mmol), ammonium acetate (3.88 g, 50 mmol), and2-trifluoridphenylaldehyde (609 mg, 3.5 mmol) in 10 mL of glacial acetic acid was refluxed for 2 h. The cooled deep red solution was diluted with 25 mL of water and neutralized with ammonium hydroxide.Then the mixture was filtered and the precipitates washed with water and acetone, then dried andpurified by chromatography over 60-80 mesh SiO2 using absolute ethanol as eluent. The obtained yield was 516 mg (54%) [32].
With ammonium acetate; glacial acetic acid; at 100℃; for 0.333333h;Microwave irradiation; General procedure: Phenanthroimidazole derivatives were synthesized in accordancewith the literature procedure with some modifications. Generally, amixture of 1,10-phenanthroline-5,6-dione (1.50 mmol), benzaldehyde(2.25 mmol), ammonium acetate (51.9 mmol), and glacial acetic acidwas heated at 100 C for 20 min under microwave irradiation (Scheme1). Then, 20 mL of water was added, and the pH value was adjusted to 7.0 at room temperature [47-49]. The solution was filtered and dried ina vacuum to obtain a yellow precipitate. The product was purified in asilica gel column by using ethanol as eluent. The target compoundswere characterized by ESI-MS and 1H- and 13C NMR spectroscopy.
With ammonium acetate; glacial acetic acid; at 130℃; for 4h; A cooled mixture of conc. H2SO4-HNO3 (60 mL, 2:1, v/v) was addedwith 1,10-phenanthroline (4 g, 22 mmol) and KBr (4 g, 33 mmol) andstirred at 130 C for 3 h. A yellow solution was cautiously neutralizedwith NaOH solution (10 molL 1) until its pH was neutral. The resultingmixture was extracted with CH2Cl2 and dried with anhydrous Na2SO4.Afterward, solvents were removed, and PDO was obtained as a yellowsolid. Then, PDO (0.420 g, 2 mmol), 4-carboxybenzaldehyde (0.360 g,2.4 mmol), and CH3COONH4 (3.2 g, 41.5 mmol) were mixed in 50 mL ofCH3COOH and stirred at 130 C for 4 h. After being cooled to roomtemperature, the solution was adjusted to pH 5.0 by adding NH3H2O(25 wt%) solution while stirring, and HNCP was dried in vacuum. HNCP(0.34 g, 0.79 mmol), 1,2-diaminobenzene (0.325 g, 3 mmol), 1-hydroxybenzotriazole(HOBT; 0.135 g, 1 mmol), N,Ndicyclohexylcarbodiimide(DCC; 0.248 g, 1.2 mmol), and triethylamine(167 μL) were dissolved in 30 mL of DMF at 4 C for 2 h whilestirring. The resulting mixture was stirred at room temperature for 24 hunder a N2 atmosphere. The faint yellow solid was filtered, washed withCH2Cl2 and Et2OH, and dried in vacuum.

  • 3
  • ammonium hexafluorophosphate [ No CAS ]
  • dichlorobis(1,10-phenanthroline)ruthenium(II) dihydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ruthenium(II)(1,10-phenanthroline)(2-[4-phenylcarboxy]-1H-imidazol[4,5-f][1,1]phenanthroline)](PF6)2 [ No CAS ]
  • 4
  • ammonium hexafluorophosphate [ No CAS ]
  • bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate [ No CAS ]
  • [ 865169-07-9 ]
  • bis(2,2'-bipyridine)(2-(4-carboxyphenyl)imidazo[4,5-f][1,10]phenanthroline)ruthenium(II) hexafluorophosphate [ No CAS ]
  • 5
  • [ 766541-21-3 ]
  • [ 865169-07-9 ]
  • [ 1165792-43-7 ]
  • 6
  • europium(III) tris(4,4,4-trifluoro-1-phenyl-1,3-butanedionate) dihydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ 1276122-94-1 ]
  • 7
  • [ 865169-07-9 ]
  • iridium(III) di-μ-chlorotetrakis(2-(2,4-difluorophenyl)pyridinato-N,C2') [ No CAS ]
  • [ 1418001-10-1 ]
YieldReaction ConditionsOperation in experiment
78% Iridium di-μ-chloro-tetrakis(2-(2, 4-difluorophenyl)pyridinato-N, C2′) (220 mg, 0.181 mmol), 2-(4-Carboxylphenyl)imidazo[4,5-f][1,10]phenanthroline [(picCOOH)] (130 mg, 0.380 mmol) and ethanol (30 mL) were added to a round bottomed flask and left refluxing at 95 C overnight. The reaction was allowed cool to room temperature and the solvent removed by warming under reduced pressure. The solid was suspended in a saturated solution of sodium perchlorate and sonicated. The precipitate was collected by vacuum filtration and washed with deionised water. The precipitate was then dissolved in methanol and filtered once again. The filtrate was taken and evaporated to dryness to yield a yellow coloured solid (285 mg, 78 1H NMR (400 MHz, DMSO-d6): δ (ppm) 9.22 (d, 2 H, 8 Hz), 8.41 (d, 2 H, J = 8 Hz), 8.29 (d, 2 H, J = 9.2 Hz), 8.22 (d, 2 H, J = 4.4 Hz), 8.17 (d, 2 H, J = 8.4 Hz), 8.07 (dd, 2 H, J = 5.2 Hz, J = 8 Hz), 7.98 (t, 2 H, J = 7.6 Hz), 7.58 (d, 2 H, J = 5.6 Hz), 7.09-6.99 (m, 4 H), 5.71 (dd, 2 H, J = 2 Hz, 2.4 Hz). Electron spray ionisation-mass spectrometry (ESI-MS): (CH3OH, m/z): 1012.39, ([M+-ClO4]): 913.1. Elemental analysis calculated for C42H24F4IrN6O2.(ClO4-).(H2O)2: C, 48.12; H, 2.69; N, 8.02%. Found: C, 48.35; H, 2.31; N, 7.86%.
  • 8
  • [ 37366-09-9 ]
  • [ 865169-07-9 ]
  • [ 1442692-01-4 ]
YieldReaction ConditionsOperation in experiment
45.7% In dichloromethane; at 60℃; for 0.5h;Microwave irradiation; General procedure: A mixture of [(C6H6)RuCl2]2 (0.1 mmol, 50 mg) and 1a, 2a, 3a, 4a,5a, 6a and 7a (0.2 mmol) in 20 ml of dichloromethane was heated in microwave reactor at 60 C for 30 min. The solvent was removed by rotary evaporation and the residue was dissolved in minimum amounts of methanol and then filtered to remove unreacted ligand to obtain a yellow crude product after recrystallization. 1b: yield: 91.2%. ESI-MS (in MeOH): m/z 435.1, ([M - Cl]+). UV-visible in MeOH [λmax, nm (ε/M-1 cm-1)]: 249 (29,585), 295 (20,095). IR (in KBr, νmax/cm-1): 3855.9, 3390.64, 3050.41, 1621.98, 1603.62, 1536.61, 1478.49, 1252.77, 1198.21, 1084.36, 848.13, 811.34, 724.29 cm-1 . 1H NMR (DMSO-d6, δ ppm) δ 9.84 (d, J = 5.0 Hz, 2H),9.22 (d, J = 7.9 Hz, 2H), 8.60 (d, J = 8.1 Hz, 2H), 8.09 (dd, J = 8.1,5.3 Hz, 1H), 6.31 (s, 6H). 13C NMR (126 MHz, DMSO) δ 155.93 (s), 145.19 (s), 144.96 (s), 134.34 (s), 128.00 (s), 88.67 (s). 2b: yield: 90.3%. ESI-MS (in MeOH): m/z 554.1, ([M -Cl]+). UV-visible in MeOH [λmax, nm (ε/M-1 cm-1)]: 290 (43,780), 342 (38,460). IR (in KBr, νmax/cm-1): 3859.28, 3389.91, 3057.66, 1608.17, 1529.30, 1486.91, 1202.82, 823.99, 812.25, 722.79. 1H NMR (in DMSO-d6, δ/ppm): 10.20-9.76 (2H, m), 9.60 (2H, t, J = 22.3 Hz), 9.40 (2H, d, J = 8.2 Hz), 9.11 (2H, dd, J = 17.3, 8.0 Hz), 8.57-8.29 (2H, m), 8.28-8.07 (2H, m), 6.91 (2H, t, J = 16.9 Hz), 6.45-6.19 (6H, m). 13C NMR(126 MHz, DMSO) δ 190.31 (s), 151.87 (s), 128.49 (s), 126.17 (s), 116.98 (s), 112.21 (s), 111.50 (s), 87.19 (s). 3b: yield: 91.4%. ESI-MS (in MeOH): m/z 541.13, ([M -Cl]+) . UV-visible in MeOH [λmax, nm (ε/M-1 cm-1)]: 289 (41,520). IR (in KBr, νmax/cm-1): 3862.15, 3423.39, 2987.91, 1610.97, 1524.46, 1483.18, 1255.81, 1181.77, 1066.11, 839.63, 810.66, 722.07. 1H NMR (DMSO-d6, δ/ppm): 9.96 (dd, J = 5.3, 1.1 Hz, 2H), 8.42 (d, J = 8.6 Hz, 2H), 8.21 (s, 2H), 7.73 (d, J = 8.7 Hz, 2H), 7.37 (s, 2H), 6.33 (s, 6H). 13C NMR (126 MHz, DMSO) δ 162.61 (s), 155.41 (s), 144.84 (s), 134.43 (s), 130.27 (s), 127.64 (s), 116.29 (s), 88.63 (s), 57.30 (s). 4b: yield: 90.8%. ESI-MS (in MeOH): m/z 527.07 ([M -Cl]+). UV-visible in MeOH [λmax, nm (ε/M-1 cm-1)]: 287 (46,030). IR (in KBr, νmax/cm-1): 3865.69, 3400.23, 3068.44, 1611.12, 1481.83, 1276.56, 1175.75, 842.83, 808.44, 721.33. 1H NMR (in DMSO-d6, δ/ppm): 9.70 (d, J = 5.2 Hz, 2H), 9.07 (d, J = 7.2 Hz, 2H), 8.76 (d, J = 7.9 Hz, 2H), 8.11 (d, J = 10.6 Hz, 2H), 7.96 (dd, J = 8.2, 5.2 Hz, 2H), 7.37 (s, 2H), 6.28 (s, 6H). 13C NMR (126 MHz, DMSO) δ 161.47 (s), 155.15 (s), 135.98 (s), 129.69 (s), 117.71 (s), 88.65 (s). 5b: yield: 45.7%. ESI-MS (in MeOH): m/z 555.13, ([M -Cl]+). UV-visible in MeOH [λmax, nm (ε/M-1 cm-1)]: 280 (35,385). IR (in KBr, νmax/cm-1): 3860.42, 3414.54, 3080.94, 1612.23, 1548.55, 1481.39, 1253.06, 1182.67, 1072.72, 838.57, 806.33, 738.21. 1H NMR (DMSO-d6, δ/ppm): 9.96 (d, J = 4.7 Hz, 2H), 9.20 (dd, J = 31.3, 7.5 Hz, 2H), 8.70 (s, 2H), 8.32-8.06 (m, 2H), 7.37 (s, 2H), 6.32 (s, 6H). 13C NMR (126 MHz, DMSO) δ 156.04 (s), 153.65 (s), 145.34 (s), 131.84 (s), 128.64 (s), 127.96 (s), 88.70 (s). 6b: yield: 91.3%. ESI-MS (in MeOH): m/z 579.13 ([M -Cl]+). UV-visible in MeOH [λmax, nm (ε/M-1 cm-1)]: 290 (41,885). IR (in KBr, νmax/cm-1): 66.14, 3401.22, 3059.80, 1607.30, 1620.53, 1551.47, 1454.98, 1167.3, 851.02, 810.46, 722.48. 1H NMR (DMSO-d6, δ ppm): 9.91 (d, J = 4.7 Hz, 2H), 8.31 (t, J = 11.1 Hz, 2H), 8.13 (dd, J = 23.8, 15.5 Hz, 2H), 7.37 (s, 2H), 6.98 (d, J 8.7 Hz, 2H), 6.32 (s, 6H). 13C NMR (126 MHz, DMSO) δ 156.03 (s), 145.39 (s), 129.24 (s), 127.95 (s), 88.70 (s). 7b: yield: 89.8%. ESI-MS (in MeOH): m/z 590.9, ([M -Cl]+). UV-visible in MeOH [λmax, nm (ε/M-1 cm-1)]: 283 (46,320). IR (in KBr, νmax/cm-1): 3869.75, 3369.99, 3042.42, 1625.14, 1603.67, 1543.71, 1459.87, 1275.97, 1186.24, 1070.50, 722.92. 1H NMR (DMSO-d6, δ ppm) δ 9.93 (dd, J = 5.3, 1.1 Hz, 2H), 8.31 (d, J = 8.6 Hz, 2H), 8.18 (dd, J = 8.1, 5.5 Hz, 2H), 7.84 (d, J = 8.6 Hz, 2H), 7.34 (s, 2H), 6.30 (s, 6H). 13C NMR (126 MHz, DMSO) δ 150.45 (s), 133.93 (s), 131.31 (s), 130.17 (s), 127.35 (s), 124.51 (s), 88.59 (s).
  • 9
  • cobalt(II) nitrate hexahydrate [ No CAS ]
  • [ 100-21-0 ]
  • [ 865169-07-9 ]
  • [Co2(1,4-BDC)(NCP)2]n·4nH2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With sodium hydroxide; In water; at 20 - 179.84℃; for 72.5h;pH 8-9;High pressure; Autoclave; Co(NO3)2·6H2O(0.15 mmol, 0.0437 g), 1,4-H2BDC (0.1 mmol, 0.0166 g) and HNCP (0.1 mmol,0.0340 g) were mixed in 10 ml deionized water. Its pH value was controlled inthe range of 8-9 with 1 mol·l-1 NaOH solution. The resulting solution was stirred for about 0.5 h at room temperature, then sealed in a 25 ml Teflon-lined stainless steel autoclave and heated at 453 K for 3 days under autogenous pressure. Afterwards, the reaction system was cooled slowly to room temperature. Brown block-shaped crystals of complex 1 suitable for single-crystal X-ray diffraction analysis were collected from the final reaction system by filtration, washed several times with distilled water and dried in air at ambient temperature (yield 45%, based on Co). Anal. Calcd for C24H17CoN4O6: C 55.83, H 3.32, N10.85%. Found: C 55.71, H 3.47, N 10.90%. FT-IR (KBr, cm-1): 3426(w), 3057(m), 2362(s), 1610(s), 1551(s), 1404(s), 1282(s), 1119(m), 1072(m),1015(w), 820(s), 729(s), 530(s), 419(m) (Fig. S3). The result can be reproduced well in parallel experiments.
  • 10
  • europium(III) chloride hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ 13731-82-3 ]
  • Eu(3+)*C20H11N4O2(1-)*C8H2Br2O4(2-) [ No CAS ]
  • 11
  • europium(III) chloride hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ 787-70-2 ]
  • Eu(3+)*C20H11N4O2(1-)*C14H8O4(2-) [ No CAS ]
  • 12
  • europium(III) chloride hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ 605-70-9 ]
  • Eu(3+)*C20H11N4O2(1-)*C12H6O4(2-)*2H2O [ No CAS ]
  • 13
  • [ 100-21-0 ]
  • europium(III) chloride hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • Eu(3+)*C8H4O4(2-)*C20H11N4O2(1-) [ No CAS ]
  • 14
  • [ 79982-56-2 ]
  • [ 75-09-2 ]
  • [ 865169-07-9 ]
  • lithium perchlorate [ No CAS ]
  • osmium(II) (bis-2,2-bipyridyl)-2(4-carboxylphenyl)imidazo[4,5f][1,10]phenanthroline perchlorate*2.5dichloromethane [ No CAS ]
  • 15
  • [ 865169-07-9 ]
  • calcium chloride [ No CAS ]
  • 2C20H11N4O2(1-)*Ca(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In water; at 180℃; for 72h;Autoclave; A mixture of <strong>[865169-07-9]2-(4-carboxyphenyl)imidazo(4,5-f)(1,10)phenanthroline</strong>) (17.0 mg, 0.05 mmol), calcium chloride (3.3 mg, 0.03 mmol)and water (10 mL) was homogenized by stirring for 30 min, then transferred into 25 mL Teflon-lined stainless steel autoclave under autogenous pressure at 180 C for 3 days. After cooling the reaction system to room temperature at a rate of 5 C/h, clear block orange crystals were isolated (with the yield of 65%, based on the HNCP reagent). Calc. for C40H22N8O4Ca (%): C, 66.84; H, 3.09.; N, 15.59. Found: C, 66.81; H, 3.01; N, 15.53. IR data (KBr pellet, cm-1): 3227(br), 3043(w), 1933(w), 1665(m), 1612(m), 1593(s), 1573(s), 1557(s), 1522(s), 1483(m), 1451(m), 1433(m), 1402(s), 1386(s), 1321(m), 1290(m), 1273(m), 1232(m), 1183(m), 1125(w), 1103(w), 1072(m), 1033 (m), 973(w), 867(m), 843(m), 807(s), 785(s), 737(s), 723(m), 705(s), 643(w), 631(w), 545(w), 529(w), 439(w), 415(m).
  • 16
  • strontium nitrate [ No CAS ]
  • [ 865169-07-9 ]
  • 2C20H11N4O2(1-)*Sr(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% In water; at 180℃; for 72h;Autoclave; A mixture of <strong>[865169-07-9]2-(4-carboxyphenyl)imidazo(4,5-f)(1,10)phenanthroline</strong>) (34.0 mg, 0.1 mmol), strontium nitrate (12.7 mg, 0.6 mmol)and water (10 mL) was homogenized by stirring for 30 min, then transferred into 25 mL Teflon-lined stainless steel autoclave under autogenous pressure at 180 C for 3 days. After cooling the reaction system to room temperature at a rate of 5 C/h, clear block orange crystals were isolated (with the yield of 61%, based on the HNCP reagent). Calc. for C40H22N8O4Sr (%): C, 70.58; H, 3.55.; N, 16.46. Found: C, 70.51; H, 3.51; N, 16.42. IR data (KBr pellet, cm-1): 3228(br), 3045(w), 1931(w), 1668(m), 1615(m), 1596(s), 1571(s), 1554(s), 1521(s), 1480(m), 1452(m), 1430(m), 1400(s), 1385(s), 1320(m), 1291(m), 1275(m), 1234(m), 1185(m), 1127(w), 1105(w), 1070(m), 1031(m), 971(w), 869(m), 845(m), 809(s), 789(s), 739(s), 724(m), 704(s), 645(w), 631(w), 547(w), 528(w), 438(w), 411(m).
  • 17
  • zinc(II) sulfate hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ 618-83-7 ]
  • C20H12N4O2*C8H4O5(2-)*Zn(2+)*2H2O [ No CAS ]
  • 18
  • zinc(II) sulfate hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ 618-88-2 ]
  • [Zn(2-(4-carboxyphenyl)imidazo[4,5-f]-1,10-phenanthroline)(5-nitroisophthalate)]n [ No CAS ]
  • 19
  • zinc(II) sulfate hexahydrate [ No CAS ]
  • [ 121-91-5 ]
  • [ 865169-07-9 ]
  • C20H12N4O2*C8H4O4(2-)*Zn(2+)*H2O [ No CAS ]
  • 20
  • cadmium sulfate octahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ 618-88-2 ]
  • [Cd(2-(4-carboxyphenyl)imidazo[4,5-f]-1,10-phenanthroline)(5-nitroisophthalate)]n [ No CAS ]
  • 21
  • [ 100-26-5 ]
  • lanthanum(III) nitrate hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • La(3+)*C20H11N4O2(1-)*C7H3NO4(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With sodium hydroxide; In water; at 179.84℃; for 72h;pH 8 - 9;Autoclave; High pressure; General procedure: PrCl3·7H2O (0.1mmol), HNCP (0.1mmol) and 2,5-H2pydc (0.1mmol) were mixed in 10ml deionized water. And its pH value was controlled in the range of 8-9 with 1mol·L-1 NaOH solution. The resulting precursor was sealed in 25ml Teflon-lined stainless steel reactor and heated at 453K for 3d under autogenous pressure. The reaction system was then cooled slowly to room temperature. The obtained solid is a mixture of yellow block crystals and powder. The crystals of 1 suitable for X-ray single-crystal diffraction analysis are picked out from the solid mixture in 61% yield based on PrCl3·7H2O. Syntheses of [Ln(NCP)(2,5-pydc)]n (Ln=La(2), Nd(3), Sm(4)). The complexes 2, 3 and 4 were prepared as described as for 1 above, except that Ln(NO3)3·6H2O was used instead of PrCl3·7H2O. The crystals of complexes 2-4 are picked out from the solid mixture in 67%, 65% and 72% yield based on Ln(NO3)3·6H2O, respectively. Anal. Calcd for C54H34N10O15Pr2 (1): C 48.23, H 2.55, N 10.42%. Found: C 48.01, H 2.63, N 10.10%. Anal. Calcd for C27H14N5O6La (2): C 50.41, H 2.19, N 10.89%. Found: C 50.13, H 2.33, N 10.84%. Anal. Calcd for C27H14N5O6Nd (3): C 49.99, H 2.18, N 10.80%. Found: C 50.03, H 2.25, N 10.77%. C27H14N5O6Sm (4): C 49.53, H 2.16, N 10.70%. Found: C 49.47, H 2.20, N 10.67%.
  • 22
  • [ 100-26-5 ]
  • neodymium(III) nitrate hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • Nd(3+)*C20H11N4O2(1-)*C7H3NO4(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydroxide; In water; at 179.84℃; for 72h;pH 8 - 9;Autoclave; High pressure; General procedure: PrCl3·7H2O (0.1mmol), HNCP (0.1mmol) and 2,5-H2pydc (0.1mmol) were mixed in 10ml deionized water. And its pH value was controlled in the range of 8-9 with 1mol·L-1 NaOH solution. The resulting precursor was sealed in 25ml Teflon-lined stainless steel reactor and heated at 453K for 3d under autogenous pressure. The reaction system was then cooled slowly to room temperature. The obtained solid is a mixture of yellow block crystals and powder. The crystals of 1 suitable for X-ray single-crystal diffraction analysis are picked out from the solid mixture in 61% yield based on PrCl3·7H2O. Syntheses of [Ln(NCP)(2,5-pydc)]n (Ln=La(2), Nd(3), Sm(4)). The complexes 2, 3 and 4 were prepared as described as for 1 above, except that Ln(NO3)3·6H2O was used instead of PrCl3·7H2O. The crystals of complexes 2-4 are picked out from the solid mixture in 67%, 65% and 72% yield based on Ln(NO3)3·6H2O, respectively. Anal. Calcd for C54H34N10O15Pr2 (1): C 48.23, H 2.55, N 10.42%. Found: C 48.01, H 2.63, N 10.10%. Anal. Calcd for C27H14N5O6La (2): C 50.41, H 2.19, N 10.89%. Found: C 50.13, H 2.33, N 10.84%. Anal. Calcd for C27H14N5O6Nd (3): C 49.99, H 2.18, N 10.80%. Found: C 50.03, H 2.25, N 10.77%. C27H14N5O6Sm (4): C 49.53, H 2.16, N 10.70%. Found: C 49.47, H 2.20, N 10.67%.
  • 23
  • [ 100-26-5 ]
  • samarium(III) nitrate hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • Sm(3+)*C20H11N4O2(1-)*C7H3NO4(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydroxide; In water; at 179.84℃; for 72h;pH 8 - 9;Autoclave; High pressure; General procedure: PrCl3·7H2O (0.1mmol), HNCP (0.1mmol) and 2,5-H2pydc (0.1mmol) were mixed in 10ml deionized water. And its pH value was controlled in the range of 8-9 with 1mol·L-1 NaOH solution. The resulting precursor was sealed in 25ml Teflon-lined stainless steel reactor and heated at 453K for 3d under autogenous pressure. The reaction system was then cooled slowly to room temperature. The obtained solid is a mixture of yellow block crystals and powder. The crystals of 1 suitable for X-ray single-crystal diffraction analysis are picked out from the solid mixture in 61% yield based on PrCl3·7H2O. Syntheses of [Ln(NCP)(2,5-pydc)]n (Ln=La(2), Nd(3), Sm(4)). The complexes 2, 3 and 4 were prepared as described as for 1 above, except that Ln(NO3)3·6H2O was used instead of PrCl3·7H2O. The crystals of complexes 2-4 are picked out from the solid mixture in 67%, 65% and 72% yield based on Ln(NO3)3·6H2O, respectively. Anal. Calcd for C54H34N10O15Pr2 (1): C 48.23, H 2.55, N 10.42%. Found: C 48.01, H 2.63, N 10.10%. Anal. Calcd for C27H14N5O6La (2): C 50.41, H 2.19, N 10.89%. Found: C 50.13, H 2.33, N 10.84%. Anal. Calcd for C27H14N5O6Nd (3): C 49.99, H 2.18, N 10.80%. Found: C 50.03, H 2.25, N 10.77%. C27H14N5O6Sm (4): C 49.53, H 2.16, N 10.70%. Found: C 49.47, H 2.20, N 10.67%.
  • 24
  • [ 100-26-5 ]
  • [ 865169-07-9 ]
  • praseodymium (III) chloride heptahydrate [ No CAS ]
  • [ 7732-18-5 ]
  • Pr(3+)*C20H11N4O2(1-)*C7H3NO4(2-)*1.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With sodium hydroxide; at 179.84℃; for 72h;pH 8 - 9;Autoclave; High pressure; PrCl3·7H2O (0.1mmol), HNCP (0.1mmol) and 2,5-H2pydc (0.1mmol) were mixed in 10ml deionized water. And its pH value was controlled in the range of 8-9 with 1mol·L-1 NaOH solution. The resulting precursor was sealed in 25ml Teflon-lined stainless steel reactor and heated at 453K for 3d under autogenous pressure. The reaction system was then cooled slowly to room temperature. The obtained solid is a mixture of yellow block crystals and powder. The crystals of 1 suitable for X-ray single-crystal diffraction analysis are picked out from the solid mixture in 61% yield based on PrCl3·7H2O. Syntheses of [Ln(NCP)(2,5-pydc)]n (Ln=La(2), Nd(3), Sm(4)). The complexes 2, 3 and 4 were prepared as described as for 1 above, except that Ln(NO3)3·6H2O was used instead of PrCl3·7H2O. The crystals of complexes 2-4 are picked out from the solid mixture in 67%, 65% and 72% yield based on Ln(NO3)3·6H2O, respectively. Anal. Calcd for C54H34N10O15Pr2 (1): C 48.23, H 2.55, N 10.42%. Found: C 48.01, H 2.63, N 10.10%. Anal. Calcd for C27H14N5O6La (2): C 50.41, H 2.19, N 10.89%. Found: C 50.13, H 2.33, N 10.84%. Anal. Calcd for C27H14N5O6Nd (3): C 49.99, H 2.18, N 10.80%. Found: C 50.03, H 2.25, N 10.77%. C27H14N5O6Sm (4): C 49.53, H 2.16, N 10.70%. Found: C 49.47, H 2.20, N 10.67%.
  • 25
  • dichlorobis(1,10-phenanthroline)ruthenium(II) dihydrate [ No CAS ]
  • [ 865169-07-9 ]
  • sodium perchlorate [ No CAS ]
  • [Ru(phen)2((4-carboxylphenyl)imidazo[4,5-f][1,10]phenanthroline)]2+2ClO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% General procedure: 1 was synthesized by the literature procedure [34] with some modifications. [Ru(phen)2Cl2]·2H2O(106 mg, 0.20 mmol) and o-TFPIP (76 mg, 0.20 mmol) were added to 10 cm3 of ethylene glycol. Themixture was refluxed for 2 h under an argon atmosphere. The cooled reaction mixture was dilutedwith water (20 cm3) and filtered to remove solid impurities. The complex was then separated fromsoluble impurities by precipitation with NaClO4. The precipitated complex was dried, dissolvedin a small amount of MeOH, and purified by chromatography over alumina oxide using MeOH-MeCN (10 : 1, v/v) as an eluent, yield: 157 mg (73%, calculated from [Ru(bpy)2Cl2]·2H2O).
  • 26
  • iron(II) ammonium sulfate [ No CAS ]
  • [ 865169-07-9 ]
  • [Fe(II)(2-(4-carboxyphenyl)imidazo[4,5-f ][1,10]phenanthroline)3]SO4 [ No CAS ]
  • 27
  • europium(III) nitrate hexahydrate [ No CAS ]
  • [ 100-21-0 ]
  • [ 865169-07-9 ]
  • [ 7732-18-5 ]
  • [Eu(NCP)(1,4-bdc)]n0.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.0% With sodium hydroxide; at 179.84℃; for 72h;pH 7.0;Autoclave; A mixture of 12 Eu(NO3)3·6H2O (0.0446g, 0.1mmol), 4-HNCP (0.0340g, 0.1mmol), 1,4-H2bdc (0.0166g, 0.1mmol), 0.1mL 13 DMF and 10mL of deionized 14 water was stirred for 10min, then the pH value was adjusted to 7.0 by the addition of 15 NaOH solution (1mol·L-1). The resultant solution was heated at 453K in a 25mL Teflon-lined stainless steel autoclave under autogenous pressure for 3days. Afterwards, the reaction system was cooled slowly to room temperature. The obtained solid is a mixture of yellow block crystals and powder. The crystals of complex 5 1 are obtained, filtered from the colorless mother liquor, washed with distilled water and air dried at room temperature (31mg, yield 70.0% based on Eu(NO3)3·6H2O). Anal. Calcd. for C28H17EuN4O7 (1, %): C, 49.94; H, 2.54; N, 8.32. Found (%): C, 49.90; H, 2.81; N, 8.27. IR (KBr pellet, cm-1): complex 1: v=3451s (ν(O-H)), 1607s (ν(C=N)), 1553s (νas(COO-)), 1399s (νs(COO-)), 1070s (ν(C-C)), 851w (δ(C-H)), 741m (δ(C-H)), 522s (ν(Eu-N)), 413m (ν(Eu-O)). Fig. S1a exhibits the IR spectrum of the complex 1
  • 28
  • europium(III) nitrate hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [ 7732-18-5 ]
  • [ 787-70-2 ]
  • [Eu(NCP)(4,4'-bpdc)]n0.75H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydroxide; at 179.84℃; for 72h;pH 7.0;Autoclave; General procedure: A mixture of 12 Eu(NO3)3·6H2O (0.0446g, 0.1mmol), 4-HNCP (0.0340g, 0.1mmol), 1,4-H2bdc (0.0166g, 0.1mmol), 0.1mL 13 DMF and 10mL of deionized 14 water was stirred for 10min, then the pH value was adjusted to 7.0 by the addition of 15 NaOH solution (1mol·L-1). The resultant solution was heated at 453K in a 25mL Teflon-lined stainless steel autoclave under autogenous pressure for 3days. Afterwards, the reaction system was cooled slowly to room temperature. An identical procedure with 1 was followed to prepare 2 except 1,4-H2bdc was replaced by 4,4′-H2bpdc. Yellow block crystals of 2 suitable for single-crystal X-ray diffraction analysis were collected by filtration, washed several times with distilled water and then saved in the clean saturated mother liquor (32mg, yield 73% based on Eu(NO3)3·6H2O). Anal. Calcd. for C34H25EuN4O9 (2, %): C, 51.98; H, 3.21; N, 7.13. Found (%): C, 51.90; H, 3.37; N, 7.16. IR (KBr pellet, cm-1): Complex 2: v=3440s (ν(O-H)), 1586s (ν(C=N)), 1509s (νas(COO-))), 1400s (νs(COO-)), 1070s (ν(C-C)), 851w (δ(C-H)), 763s (δ(C-H)), 533s (ν(Eu-N)), 413m (ν(Eu-O)). Fig. S1b exhibits the IR spectrum of the complex 2
  • 29
  • samarium(III) nitrate hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [Sm2(cpip)2(OAc)4]n [ No CAS ]
  • 30
  • europium(III) nitrate hexahydrate [ No CAS ]
  • [ 865169-07-9 ]
  • [Eu2(cpip)2(OAc)4]n [ No CAS ]
  • 31
  • [ 4282-31-9 ]
  • [ 865169-07-9 ]
  • samarium(III) chloride hexahydrate [ No CAS ]
  • C20H11N4O2(1-)*C6H2O4S(2-)*Sm(3+) [ No CAS ]
  • 32
  • [ 4282-31-9 ]
  • [ 865169-07-9 ]
  • neodymium(III) chloride hexahydrate [ No CAS ]
  • C20H11N4O2(1-)*C6H2O4S(2-)*Nd(3+)*H2O [ No CAS ]
  • 33
  • [ 4282-31-9 ]
  • [ 865169-07-9 ]
  • praseodymium(III) chloride hexahydrate [ No CAS ]
  • C20H11N4O2(1-)*C6H2O4S(2-)*0.5H2O*Pr(3+) [ No CAS ]
  • 34
  • [ 15746-57-3 ]
  • [ 865169-07-9 ]
  • [ 1164127-00-7 ]
YieldReaction ConditionsOperation in experiment
78% Synthetic procedure steps and NMR spectra of [Ru(bpy)2(CIPH2)]2+complex for convenience referred as Ru-CIP complex are described inElectronic supporting information. The complex Ru-CIP has been synthesizedby following slightly modified reported literature method[34,35]. Briefly, 110 phenanthroline-5,6-dione via Steck and Dey [36]coupling with 4-carboxybenzaldehyde formed 4-carboxyl-imidado[4,5-f][1,10]-phenanthroline (CIP) ligand. In a typical reaction Ru(bpy)2Cl2(146 mg, 0.30 mmol, 1.0 eq) was treated with silver nitrate (102 mg,0.60 mmol, 2.0 eq) in methanol for 3 h at room temperature. The solutionwas filtered in order to remove silver salts and the filtrate wasadded to a round bottom flask containing CIP ligand (98 mg,0.30 mmol, 1.0 eq). The solution was refluxed for 3 h in dark under anargon atmosphere. At this time the reaction mixture was allowed to goto room temperature and the solvent was evaporated under reducedpressure. The obtained solid was washed repeatedly with copiousquantity of diethyl ether; the obtained product was dried under vacuum (243 mg).Yield: 78%.
  • 36
  • [ 15746-57-3 ]
  • [ 865169-07-9 ]
  • C40H28N8O2Ru(2+)*2Cl(1-) [ No CAS ]
  • 37
  • [ 135515-70-7 ]
  • [ 865169-07-9 ]
  • C29H17ClN6O4Ru [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% In ethanol; water; for 8h;Reflux; Inert atmosphere; [(CH3)4N][RuCl3(qn)(NO)] (45.5 mg, 0.1 mM) was dissolved in a mixed solvent of ethylalcohol (10 cm3) and distilled water (10 cm3). To this solution, picp(34.5 mg, 0.1 mM) was added. The reaction mixture was refluxedfor 8 h under an Ar atmosphere. The product was obtained as a reddishbrown precipitate and washed with ethyl alcohol, water anddiethyl ether. Yield: 30 mg (46%). 1H NMR (600 MHz, DMSO d6)d, ppm: 9.71 (s, 1H), 9.58 (s, 1H), 9.35 (d, J = 22.8 Hz, 2H), 8.86(d, J = 8.1 Hz, 1H), 8.50 (d, J = 7.4 Hz, 3H), 8.30-7.92 (m, 4H),7.76 (d, J = 53.7 Hz, 2H), 7.52 (d, J = 8.8 Hz, 1H), 6.79(d, J = 6.3 Hz, 1H). ESI-MS: Exact mass calcd for C29H18ClN6O4Ru[M+H]+: 651.0122. Found: 651.0120.
  • 38
  • [ 865169-07-9 ]
  • C8H12CuN4(1+)*(x)F6P [ No CAS ]
  • [ 192226-54-3 ]
  • copper(I)(2,9-dimesityl-1,10-phenanthroline)[4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzoic acid] hexafluorophosphate [ No CAS ]
  • 39
  • [ 865169-07-9 ]
  • [Re(CO)3(2-(4-carboxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline)(Melm)]OTf [ No CAS ]
  • 40
  • [ 865169-07-9 ]
  • C32H19ClN9O4Re [ No CAS ]
  • 41
  • [ 865169-07-9 ]
  • C40H37ClN7O4Re [ No CAS ]
  • 42
  • [ 7647-01-0 ]
  • [ 163932-31-8 ]
  • [ 865169-07-9 ]
  • C23H12ClN4O5(99)Tc [ No CAS ]
  • 43
  • [ 865169-07-9 ]
  • r (4-(1,2,4,5-tetrazin-3-yl)phenyl)methanamine hydrochloride [ No CAS ]
  • C29H19N9O [ No CAS ]
  • 44
  • [ 14099-01-5 ]
  • [ 865169-07-9 ]
  • [Re(CO)3(2-(4-carboxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline)Cl] [ No CAS ]
  • 45
  • [ 865169-07-9 ]
  • [ 95-54-5 ]
  • N-(2-aminophenyl)-4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.37 g With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 4 - 20℃; for 24h;Inert atmosphere; A cooled mixture of conc. H2SO4-HNO3 (60 mL, 2:1, v/v) was addedwith 1,10-phenanthroline (4 g, 22 mmol) and KBr (4 g, 33 mmol) andstirred at 130 C for 3 h. A yellow solution was cautiously neutralizedwith NaOH solution (10 molL 1) until its pH was neutral. The resultingmixture was extracted with CH2Cl2 and dried with anhydrous Na2SO4.Afterward, solvents were removed, and PDO was obtained as a yellowsolid. Then, PDO (0.420 g, 2 mmol), 4-carboxybenzaldehyde (0.360 g,2.4 mmol), and CH3COONH4 (3.2 g, 41.5 mmol) were mixed in 50 mL ofCH3COOH and stirred at 130 C for 4 h. After being cooled to roomtemperature, the solution was adjusted to pH 5.0 by adding NH3H2O(25 wt%) solution while stirring, and HNCP was dried in vacuum. HNCP(0.34 g, 0.79 mmol), 1,2-diaminobenzene (0.325 g, 3 mmol), 1-hydroxybenzotriazole(HOBT; 0.135 g, 1 mmol), N,Ndicyclohexylcarbodiimide(DCC; 0.248 g, 1.2 mmol), and triethylamine(167 μL) were dissolved in 30 mL of DMF at 4 C for 2 h whilestirring. The resulting mixture was stirred at room temperature for 24 hunder a N2 atmosphere. The faint yellow solid was filtered, washed withCH2Cl2 and Et2OH, and dried in vacuum. The reaction yielded 0.370 g(yield: 71.3%) of APIPB with the following properties: 1H NMR (400MHz, DMSO-d6): δ 13.95 (s, 1H), 9.84 (s, 1H), 9.07 (s, 2H), 8.99-8.97 (d,2H), 8.44-8.42 (d, 2H), 8.25-8.23 (d, 2H), 7.92-7.84 (ddd, 2H),7.21-7.19 (d, 2H), 7.02-6.98 (t, 1H), 6.82-6.80 (d, 1H), 6.64-6.61 (t,1H), 5.05 (br, 1H) ppm. ESI-MS: m/z, [M + H]+: calcd. 431.2, found431.2
  • 46
  • [ 865169-07-9 ]
  • [ 62-53-3 ]
  • 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)-N-phenylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 4 - 20℃; for 24h;Inert atmosphere; General procedure: A cooled mixture of conc. H2SO4-HNO3 (60 mL, 2:1, v/v) was addedwith 1,10-phenanthroline (4 g, 22 mmol) and KBr (4 g, 33 mmol) andstirred at 130 C for 3 h. A yellow solution was cautiously neutralizedwith NaOH solution (10 molL 1) until its pH was neutral. The resultingmixture was extracted with CH2Cl2 and dried with anhydrous Na2SO4.Afterward, solvents were removed, and PDO was obtained as a yellowsolid. Then, PDO (0.420 g, 2 mmol), 4-carboxybenzaldehyde (0.360 g,2.4 mmol), and CH3COONH4 (3.2 g, 41.5 mmol) were mixed in 50 mL ofCH3COOH and stirred at 130 C for 4 h. After being cooled to roomtemperature, the solution was adjusted to pH 5.0 by adding NH3H2O(25 wt%) solution while stirring, and HNCP was dried in vacuum. HNCP(0.34 g, 0.79 mmol), 1,2-diaminobenzene (0.325 g, 3 mmol), 1-hydroxybenzotriazole(HOBT; 0.135 g, 1 mmol), N,Ndicyclohexylcarbodiimide(DCC; 0.248 g, 1.2 mmol), and triethylamine(167 μL) were dissolved in 30 mL of DMF at 4 C for 2 h while stirring.
  • 47
  • [ 865169-07-9 ]
  • [MnBr(CO)3(N-(2-aminophenyl)-4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzamide)] [ No CAS ]
  • 48
  • [ 865169-07-9 ]
  • 6-(4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzamido)hexanoic acid [ No CAS ]
  • 49
  • [ 865169-07-9 ]
  • C44H35IrN7O3S2(1+)*F6P(1-) [ No CAS ]
  • 50
  • [ 6066-82-6 ]
  • [ 865169-07-9 ]
  • 2,5-dioxopyrrolidin-1-yl 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.3% L1 (0.17g, 0.5mmol), N-hydroxysuccinimide (NHS) (0.1438g, 1.25mmol) and N, N-diisopropylethylamine (DIEA) (0.1935 g, 1.5mmol) were dissolved in N, N-dimethylformamide (10mL). The mixture was stirred at room temperature for 2h and then N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI) (0.24g, 1.25mmol) was added, followed by stirring for 24h. At the end of the reaction, the reaction solution was concentrated under reduced pressure to give a yellow viscous solid. The crude product was dried under vacuum and purified by silica gel column chromatography. Yield: 88.3%. Anal. calc. for C24H15N5O4: C, 65.90; H, 3.46; N, 16.01; found: C, 65.77; H, 3.39; N, 16.07. 1H NMR (400MHz, DMSO-d6) δ 14.06 (s, 1H), 9.06 (d, J=4.2Hz, 2H), 8.91 (d, J=8.1Hz, 2H), 8.51 (d, J=8.1Hz, 2H), 8.33 (d, J=8.1Hz, 2H), 7.88-7.79 (m, 2H), 2.96 (s, 4H). 13C NMR (100MHz, DMSO) δ 173.25, 170.83, 161.93, 149.00, 148.63, 144.36, 136.36, 131.32, 130.50, 130.18, 127.14, 126.58, 124.97, 123.82, 26.07, 25.70.
88.3% L1 (0.17g, 0.5mmol), N-hydroxysuccinimide (NHS) (0.1438g, 1.25mmol) and N, N-diisopropylethylamine (DIEA) (0.1935 g, 1.5mmol) were dissolved in N, N-dimethylformamide (10mL). The mixture was stirred at room temperature for 2h and then N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI) (0.24g, 1.25mmol) was added, followed by stirring for 24h. At the end of the reaction, the reaction solution was concentrated under reduced pressure to give a yellow viscous solid. The crude product was dried under vacuum and purified by silica gel column chromatography. Yield: 88.3%. Anal. calc. for C24H15N5O4: C, 65.90; H, 3.46; N, 16.01; found: C, 65.77; H, 3.39; N, 16.07. 1H NMR (400MHz, DMSO-d6) δ 14.06 (s, 1H), 9.06 (d, J=4.2Hz, 2H), 8.91 (d, J=8.1Hz, 2H), 8.51 (d, J=8.1Hz, 2H), 8.33 (d, J=8.1Hz, 2H), 7.88-7.79 (m, 2H), 2.96 (s, 4H). 13C NMR (100MHz, DMSO) δ 173.25, 170.83, 161.93, 149.00, 148.63, 144.36, 136.36, 131.32, 130.50, 130.18, 127.14, 126.58, 124.97, 123.82, 26.07, 25.70.
Same Skeleton Products
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