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[ CAS No. 405173-97-9 ] {[proInfo.proName]}

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Chemical Structure| 405173-97-9
Chemical Structure| 405173-97-9
Structure of 405173-97-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 405173-97-9 ]

CAS No. :405173-97-9 MDL No. :MFCD01029245
Formula : C9H9ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :TUGGOLWUZCCVBF-UHFFFAOYSA-N
M.W : 180.63 Pubchem ID :12216288
Synonyms :

Calculated chemistry of [ 405173-97-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.66
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 3.29
Consensus Log Po/w : 2.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.211 mg/ml ; 0.00117 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.355 mg/ml ; 0.00197 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.33
Solubility : 0.00835 mg/ml ; 0.0000462 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 405173-97-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 405173-97-9 ]

* 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 [ 405173-97-9 ]

[ 405173-97-9 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 51036-80-7 ]
  • [ 405173-97-9 ]
  • 2
  • [ 107-94-8 ]
  • [ 95-54-5 ]
  • [ 405173-97-9 ]
YieldReaction ConditionsOperation in experiment
70% With hydrogenchloride; In water;Reflux; Other bromoethylarenes were prepared according to literature procedures as shown in the schemes below. Additional bromoethylindoles were prepared by Fischer-type indole synthesis followed by bromination (Campos, K.R. et al . 2004; Mewshaw, R.R. et al . 2004) (Scheme 16), acylation of substituted indoles with oxalyl chloride (Woodward, R.B. et al . 1958) followed by reduction (Feldman, et al . 1986) and bromination (Scheme 17) . 3- (2-bromoethyl) benzofuran (Kozikowski, A. P. et al . 2007; Tomaszewski, Z. et al . 1992) and 3- (2-bromoethyl ) benzothiophene were prepared according to the protocols in Scheme 18. 3-indolylacetaldehyde was prepared by Parikh-Doering oxidation of tryptophol (Sugawara, S. et al . 2009), 3- ( 2-oxoethyl ) -lH-indole-2-carboxylate was prepared from 2- (carboethoxy) indole via literature procedures (Buechi, G. et al . 1977; Vega, A.M. et al . 1981) , and 2- (2-chloroethyl ) benzimidazole was prepared by condensation of o-phenylenediamine and 3- chloropropionic acid (Cowart, M. et al . 2004) (Scheme 19) .
  • 3
  • [ 21367-89-5 ]
  • [ 95-54-5 ]
  • [ 405173-97-9 ]
  • 4
  • [ 405173-97-9 ]
  • [ 4490-75-9 ]
  • 2-{2-[2-(1H-Benzoimidazol-2-yl)-ethylsulfanyl]-ethyl}-isoindole-1,3-dione; hydrochloride [ No CAS ]
  • 6
  • [ 34803-66-2 ]
  • [ 405173-97-9 ]
  • 2-[2-(4-pyridin-2-yl-piperazin-1-yl)-ethyl]-1<i>H</i>-benzoimidazole [ No CAS ]
  • 7
  • [ 630121-84-5 ]
  • [ 405173-97-9 ]
  • 2-[2-(3-thiazol-2-yl-piperidin-1-yl)-ethyl]-1<i>H</i>-benzoimidazole [ No CAS ]
  • 10
  • [ 405173-97-9 ]
  • N-methyl-N'-[2-(2-(2-benzimidazolyl)ethylamino)-ethyl]thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Similarly, using <strong>[405173-97-9]2-(2-chloroethyl)benzimidazole</strong>, the product is N-methyl-N'-[2-(2-(2-benzimidazolyl)ethylamino)-ethyl]thiourea.
  • 11
  • [ 4857-01-6 ]
  • [ 405173-97-9 ]
  • N-[2-(2-(2-Benzimidazolyl)ethyl)thioethyl]-N'-cyano-N"-methylguanidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; EXAMPLE 230 N-[2-(2-(2-Benzimidazolyl)ethyl)thioethyl]-N'-cyano-N"-methylguanidine Using <strong>[405173-97-9]2-(2-chloroethyl)benzimidazole</strong>, prepared by treating 2-(2-hydroxyethyl)benzimidazole with thionyl chloride, as the starting material in the procedure of Example 17 gives the title compound.
  • 12
  • [ 24424-99-5 ]
  • [ 405173-97-9 ]
  • [ 405173-98-0 ]
  • 13
  • endo-7-ethyl-2-azabicyclo[2.2.2 ]oct-5-ene hydroiodide [ No CAS ]
  • [ 405173-97-9 ]
  • endo-2-[2-(1H-benzo[d]imidazol-2-yl)ethyl]-7-ethyl-2-azabicyclo[2.2.2]oct-5-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; The crude isoquinuclidine hydroiodide (106 mg, 0.40 mmol) , obtained by TMSI deprotection of 8 and triethylamine (0.17 mL, 121 mg, 1.2 mmol) in anhydrous DMF (1.5 mL) was stirred under argon at room temperature for 10 min. 2-(2'- chloroethyl ) benzimidazole (72 mg, 0.40 mmol) was then added to the above mixture and the resulting solution was allowed to stir at room temperature overnight. After the workup, the crude mixture was purified by RP-HPLC to afford a pale yellow oil (48 mg, 43% yield) . 1R NMR (300 MHz, CD3OD) delta 7.68 (2H, dd, J= 6.2, 3.2 Hz), 7.48 (2H, dd, J= 6.2, 3.1 Hz), 6.75 (1H, dd, J= 7.7, 7.7 Hz), 6.25 (1H, dd, J= 7.7, 7.7 Hz), 4.25 (1H, d, J= 5.2 Hz), 3.60 (3H, m) , 3.45 (2H, m) , 2.93 (1H, m) , 2.80 (1H, d, J= 10.5 Hz), 2.14 (1H, m) , 1.94 (1H, ddd, J= 12.6, 9.1, 2.9 Hz), 1.25 (1H, m) , 1.04 (1H, m) , 0.94 (1H, dddd, J= 7.9, 5.2, 2.6, 2.6 Hz), 0.85 (3H, t, J= 7.4 Hz); 13C NMR (75 MHz, CD3OD) delta 150.5, 140.4, 133.5, 133.5, 127.1, 127.1, 126.0, 115.1, 115.1, 59.9, 53.6, 53.3, 37.1, 30.8, 29.1, 28.9, 23.5, 11.3; m/z calcd for C18H23N3 281.19, found 281.73.
  • 14
  • 2-(2-aminoethyl)-N-(pyridin-2-ylmethyl)-1,3-thiazole-4-carboxamide dihydrochloride [ No CAS ]
  • [ 405173-97-9 ]
  • 2-(2-[2-(1H-1,3-benzodiazol-2-yl)ethyl]amino}ethyl)-N-(pyridin-2-ylmethyl)-1,3-thiazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 30℃; for 144h; General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 - 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 - 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion to general procedure 7, 2-(2-aminoethyl)-N-(pyridin-2-ylmethyl)-1 ,3-thiazole-4- carboxamide dihydrochloride (105) (240 mg, 0.72 mmol), 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole (259 mg, 1 .43 mmol) and DIPEA (2.17 ml, 12.53 mmol) in DMF (10 ml) afforded the title compound (64 mg, 22%) as a brown solid after purification by basic prep-HPLC followed by flash column chromatography (eluting with a gradient of 0-10% MeOH / DCM followed by 0.8 M ammonia in MeOH / DCM) 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 8.87 (t, J = 6.0 Hz, 1 H), 8.50 (d, J = 4.6 Hz, 1 H), 8.10 (s, 1 H), 7.74 (td, J = 7.7, 1 .7 Hz, 1 H), 7.44 (s, 2H), 7.33 - 7.21 (m, 2H), 7.10 (dd , J = 5.9, 3.2 Hz, 2H), 4.55 (d , J = 6.0 Hz, 2H), 3.15 (t, J = 6.7 Hz, 2H), 3.02 (t, J = 6.7 Hz, 2H), 2.90 - 2.96 (m, 4H) HPLCMS (Method G): [m/z]: 407.2 [M+H]+
  • 15
  • 1-(2-aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1H-pyrazole-4-carboxamide dihydrochloride [ No CAS ]
  • [ 405173-97-9 ]
  • 1-(2-[2-(1H-1,3-benzodiazol-2-yl)ethyl]amino}ethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1H-pyrazole-4-carboxamide tetrahydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.6% General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 - 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 - 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion using general procedure 7, 1-(2-aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 H- pyrazole-4-carboxamide dihydrochloride (260) (0.7 g, 2.08 mmol), 2-(2-chloroethyl)-1 H-benzimidazole (0.451 g, 2.499 mmol) and DIPEA (5.4 ml, 31.23 mmol) in DMF (15 ml) at 3(?C for 6 d gave the product as the free base (63 mg) after purification by silica column chromatography (kpNH, eluting with a gradient of 0-40% MeOH / EtOAc) followed by basic prep-HPLC. The freebase product was dissolved in MeOH (3 ml) and 12 M HCI (2 ml) at room temperature for 2 h to give the title compound (65 mg, 5.6%) as a brown solid. 1H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.46 (s, 1H), 8.25 (s, 1H), 8.01 (s, 1H), 7.81 (dd, J = 6.2, 3.2 Hz, 3H), 7.63 (dd, J = 6.2, 3.1 Hz, 3H), 4.78 (s, 2H), 4.64 (s, 2H), 3.72 , J = 7.6 Hz, 6H) HPLCMS (Method B): [m/z]: 408.2 [M+H]+
  • 16
  • 1-(2-aminoethyl)-N-[(3-chloropyridin-2-yl)methyl]-1H-pyrazole-4-carboxamide dihydrochloride [ No CAS ]
  • [ 405173-97-9 ]
  • 1-(2-[2-(1H-1,3-benzodiazol-2-yl)ethyl]amino}ethyl)-N-[(3-chloropyridin-2-yl)methyl]-1H-pyrazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 40℃; for 156h; General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 - 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 - 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion using general procedure 7, 1-(2-aminoethyl)-N-[(3-chloropyridin-2-yl)methyl]-1H- pyrazole-4-carboxamide dihydrochloride (261) (0.45 g, 1.28 mmol), 2-(2-chloroethyl)-1H-benzimidazole (0.28 g, 1.53 mmol) and DIPEA (3.3 ml, 19.14 mmol) in DMF (7 ml) at room temperature for 66 h, then heated to 40C for 90 h, gave the title compound (112 mg, 21%) as a colourless film after purification by flash column chromatography (kp-NH, eluting with a gradient of 0-10% MeOH / DCM) followed by basic prep-HPLC. 1H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.10 (s, 1H), 8.52-8.44 (m, 2H), 8.22 (s, 1H), 7.92 (dd, J = 8.1, 1.4 Hz, 1H), 7.90 (s, 1H), 7.55-7.38 (br m, 2H), 7.37 (dd, J = 8.1, 4.7 Hz, 1H), 7.13- 7.07 (m, 2H), 4.63 (d, J = 5.7 Hz, 2H), 4.20 (t, J = 6.2 Hz, 2H), 2.99- 2.93 (m, 4H), 2.93 - 2.89 (m, 2H) HPLCMS (Method C): [m/z]: 424.1 [M+H]
  • 17
  • N-(pyridin-2-ylmethyl)-4H,5H,6H,7H-thieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
  • [ 405173-97-9 ]
  • 6-[2-(1H-1,3-benzodiazol-2-yl)ethyl]-N-(pyridin-2-ylmethyl)-4H,5H,6H,7H-thieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With potassium carbonate; In acetone; at 20℃; for 24h; General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 - 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 - 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion to general procedure 7, -(pyridin-2-ylmethyl)-4H,5H,6H,7H-thieno[2,3-c]pyridine-3- carboxamide (450) (65 mg, 0.24 mmol), K2C03 (49 mg, 0.36 mmol) and 2-(2-chloroethyl)-1 H- benzimidazole (47 mg, 0.26 mmol) in acetone (3 ml) at room temperature for 24 h, followed by the addition of DMF (5 ml), Nal (39 mg, 0.26 mmol), DIPEA (0.16 ml, 0.95 mmol) and 2-(2-chloroethyl)-1 H- benzimidazole (94 mg, 0.52 mmol) at room temperature for 72 h, gave the title compound (9 mg, 9%) as an orange solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.17 (s, 1 H), 8.75 (t, J = 6.0 Hz, 1 H), 8.50 (d, J = 4.2 Hz, 1 H), 7.94 (s, 1 H), 7.75 (td, J = 7.7, 1.8 Hz, 1 H), 7.46 (s, 2H), 7.31 (d, J = 7.8 Hz, 1 H), 7.28- 7.23 (m, 1 H), 7.10 (dd, J = 6.0, 3.1 Hz, 2H), 4.48 (d, J = 6.0 Hz, 2H), 3.71 (s, 2H), 3.05 (t, J = 7.2 Hz, 2H), 2.96 (t, J = 7.2 Hz, 2H), 2.82 (d, J = 5.3 Hz, 2H), 2.75 (t, J = 5.7 Hz, 2H) HPLCMS (Method B): [m/z]: 418.2 [M+H]+
  • 18
  • [ 405173-97-9 ]
  • [ 70458-96-7 ]
  • 7-(4-(2-(1H-benzimidazol-2-yl)ethyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
39.2% General procedure: A mixture of 73 norfloxacin (1.920g, 0.006mol), 97 potassium carbonate (0.830g, 0.006mol) and 98 potassium iodide (0.100g, 0.006mol) in 99 acetonitrile (100mL) was stirred at 50C for 1h. After the mixture was cooled to room temperature, compound 8a (1.000g, 0.006mol) was added. The reaction mixture was then heated at 50C for 3h. After the reaction was completed (monitored by TLC, chloroform/methanol (50/1, V/V)), the reaction was cooled to room temperature and treated with 90 formic acid to adjust the pH value to 5.5-6.5. After the acetonitrile was removed under reduced pressure, the mixture was purified by flash silica gel column eluting with chloroform/methanol (60/1, V/V) to give the pure target 100 compound 13a as white power (1.120g). Yield: 41.7%.
  • 19
  • [ 85721-33-1 ]
  • [ 405173-97-9 ]
  • 7-(4-(2-(1H-benzimidazol-2-yl)ethyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.5% General procedure: A mixture of 73 norfloxacin (1.920g, 0.006mol), 97 potassium carbonate (0.830g, 0.006mol) and 98 potassium iodide (0.100g, 0.006mol) in 99 acetonitrile (100mL) was stirred at 50C for 1h. After the mixture was cooled to room temperature, compound 8a (1.000g, 0.006mol) was added. The reaction mixture was then heated at 50C for 3h. After the reaction was completed (monitored by TLC, chloroform/methanol (50/1, V/V)), the reaction was cooled to room temperature and treated with 90 formic acid to adjust the pH value to 5.5-6.5. After the acetonitrile was removed under reduced pressure, the mixture was purified by flash silica gel column eluting with chloroform/methanol (60/1, V/V) to give the pure target 100 compound 13a as white power (1.120g). Yield: 41.7%.
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