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[ CAS No. 374554-54-8 ] {[proInfo.proName]}

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Chemical Structure| 374554-54-8
Chemical Structure| 374554-54-8
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Product Details of [ 374554-54-8 ]

CAS No. :374554-54-8 MDL No. :MFCD09258640
Formula : C9H7ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :DDELEGMETMZLAF-UHFFFAOYSA-N
M.W : 178.62 Pubchem ID :459771
Synonyms :

Calculated chemistry of [ 374554-54-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.16
TPSA : 38.91 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) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 2.48
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 2.36
Consensus Log Po/w : 2.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.154 mg/ml ; 0.000864 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.259 mg/ml ; 0.00145 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.96
Solubility : 0.0198 mg/ml ; 0.000111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 374554-54-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 374554-54-8 ]

* 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 [ 374554-54-8 ]

[ 374554-54-8 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 3544-25-0 ]
  • [ 374554-54-8 ]
  • [ 855268-36-9 ]
  • 3
  • [ 374554-54-8 ]
  • [ 1125-60-6 ]
  • 4
  • [ 58142-97-5 ]
  • [ 374554-54-8 ]
YieldReaction ConditionsOperation in experiment
1-Chloroisoquinolin-5-amine A mixture of <strong>[58142-97-5]1-chloro-5-nitroisoquinoline</strong> (450 mg, 0.0022 mol), stannous chloride dihydrate (2.4 g, 0.011 mol), and EtOAc (50 mL) was stirred under reflux under an atmosphere of nitrogen for 3 h. After cooling, the mixture was poured into ice-water and basified to pH 10.0 with aq. Na2CO3. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the product as a light yellow solid. LC-MS: 3.17 min, 179.2 & 181.2 (M+1).
With tin(ll) chloride; In ethyl acetate; at 20 - 70℃; for 1h; A solution (40 ml) of <strong>[58142-97-5]1-chloro-5-nitroisoquinoline</strong> (2.23 g, synthesised according to the method described in J. Med. Chem. 45, 3, 740 (2002)) in ethyl acetate was added with tin(II) chloride dihydrate (12.39 g, Wako Pure Chemical Industries) at room temperature and stirred with heating at 70 C. for 1 hour. The reaction mixture was cooled to room temperature, then added with ice (200 g) and stirred for 0.5 hour. The reaction mixture was filtered through Celite and extracted three times with ethyl acetate (200 ml for each time), and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (749 mg).
1-chloroisoquinolin-5-amine; A mixture of <strong>[58142-97-5]1-chloro-5-nitroisoquinoline</strong> (450 mg, 0.0022 mol), stannous chloride dihydrate (2.4 g, 0.011 mol), and EtOAc (50 mL) was stirred under reflux under an atmosphere of nitrogen for 3 h. After cooling, the mixture was poured into ice-water and basified to pH 10.0 with aq. Na2CO3. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the product as a light yellow solid. LC-MS: 3.17 min, 179.2 & 181.2 (M+1).
With iron; ammonium chloride; In ethanol; water; at 80℃; for 1h; To a 1000 mL 3-neck round-bottomed flask containing l-chloro-5-nitroisoquinoline (Step 1, 8.200 g, 39.3 mmol) was added Iron powder (11.80 g, 211.2 mmol), while under a flow of inert gas. A 3 : 1 mixture of EtOHTH2O (240 mL), and NH4Cl (1.19 g, 22.4 mmol) were added. The mixture was heated to 80 0C, while stirring under inert atmosphere for 1 hour. The oil bath was removed and the mixture was allowed to cool to ambient temperature. The crude material was filtered through a plug of Celite, and the filtrate was concentrated in-vacuo. Recrystallization from DCM/Hexanes, and further washing the solid with hexanes (3 x 100 mL) afforded a brown crystalline solid, which was titled product (7.015 g, 39.3 mmol). MS (ESI pos. ion) m/z: 179 (M+H). Calc'd Exact Mass for C9H7N2Cl: 178.5

  • 5
  • [ 19493-44-8 ]
  • [ 374554-54-8 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 168A 1-chloro-5-isoquinolinamine The title compound was prepared using the procedures described in Examples 60D and 60E using 1-chloroisoquinoline instead of the product from Example 60C.
Example 168A 1-chloro-5-isoquinolinamine The title compound was prepared using the procedures described in Examples 60D and 60E using 1-chloroisoquinoline instead of the product from Example 60C.
  • 7
  • [ 374554-54-8 ]
  • 1-bromo-4-(isocyanatomethyl)benzene [ No CAS ]
  • N-[(4-bromophenyl)methyl]-N'-(1-chloroisoquinolin-5-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% In toluene; EXAMPLE 64B N-[(4-bromophenyl)methyl]-N'-(1-chloroisoquinolin-5-yl)urea The product from Example 64A (520 mg, 2.91 mmol) in toluene (8 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.41 mL, 2.93 mmol) with stirring and then the mixture was heated at 90 C. for 2 hours. The mixture was allowed to cool to room temperature, filtered, the filter cake washed with toluene, and air-dried to provide the title compound as an off-white solid (717 mg, 63%). 1H NMR (300 MHz, DMSO-d6) delta 8.89 (s, 1H), 8.34-8.37 (m, 2H), 8.00 (dd, J=6.1 Hz, 0.7 Hz, 1H), 7.92-7.95 (m, 1H), 7.73 (t, J=8.1, 1H), 7.53-7.56 (m, 2H), 7.30-7.33 (m, 2H), 7.12 (t, J=5.8Hz, 1H), 4.35 (d, J=5.8 Hz, 2H); MS (ESI+) m/z 390/392 (M+H+, 35Cl/37Cl).
63% In toluene; EXAMPLE 64B N-[(4-bromophenyl)methyl]-N'-(1-chloroisoquinolin-5-yl)urea The product from Example 64A (520 mg, 2.91 mmol) in toluene (8 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.41 mL, 2.93 mmol) with stirring and then the mixture was heated at 90 C. for 2 hours. The mixture was allowed to cool to room temperature, filtered, the filter cake washed with toluene, and air-dried to provide the title compound as an off-white solid (717 mg, 63%). 1H NMR (300 MHz, DMSO-d6) delta 8.89 (s, 1H), 8.34-8.37 (m, 2H), 8.00 (dd, J=6.1 Hz, 0.7 Hz, 1H), 7.92-7.95 (m, 1H), 7.73 (t, J=8.1, 1H), 7.53-7.56 (m, 2H), 7.30-7.33 (m, 2H), 7.12 (t, J=5.8 Hz, 1H), 4.35 (d, J=5.8 Hz, 2H); MS (ESI+) m/z 390/392 (M+H+, 35Cl/37Cl).
63% In toluene; at 90℃; for 2h;Product distribution / selectivity; EXAMPLE 64B N-[(4-bromophenyl)methyl]-N'-(1-chloroisoquinolin-5-yl)urea The product from Example 64A (520 mg, 2.91 mmol) in toluene (8 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.41 mL, 2.93 mmol) with stirring and then the mixture was heated at 90 C. for 2 hours. The mixture was allowed to cool to room temperature, filtered, the filter cake washed with toluene, and air-dried to provide the title compound as an off-white solid (717 mg, 63%). 1H NMR (300 MHz, DMSO-d6) delta 8.89 (s, 1H), 8.34-8.37 (m, 2H), 8.00 (dd, J=6.1 Hz, 0.7 Hz, 1H), 7.92-7.95 (m, 1H), 7.73 (t, J=8.1, 1H), 7.53-7.56 (m, 2H), 7.30-7.33 (m, 2H), 7.12 (t, J=5.8 Hz, 1H), 4.35 (d, J=5.8 Hz, 2H); MS (ESI+) m/z 390/392 (M+H+, 35Cl/37Cl).
63% In toluene; Example 64B N-[(4-bromophenyl)methyl]-N'-(1-chloroisoquinolin-5-yl)urea The product from Example 64A (520 mg, 2.91 mmol) in toluene (8 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.41 mL, 2.93 mmol) with stirring and then the mixture was heated at 90 C. for 2 hours. The mixture was allowed to cool to room temperature, filtered, the filter cake washed with toluene, and air-dried to provide the title compound as an off-white solid (717 mg, 63%). 1H NMR (300 MHz, DMSO-d6) delta 8.89 (s, 1H), 8.34-8.37 (m, 2H), 8.00 (dd, J=6.1 Hz, 0.7 Hz, 1H), 7.92-7.95 (m, 1H), 7.73 (t, J=8.1, 1H), 7.53-7.56 (m, 2H), 7.30-7.33 (m, 2H), 7.12 (t, J=5.8 Hz, 1H), 4.35 (d, J=5.8 Hz, 2H); MS (ESI+) m/z 390/392 (M+H+, 35Cl/37Cl).

  • 8
  • [ 696-59-3 ]
  • [ 374554-54-8 ]
  • aqueous potassium carbonate [ No CAS ]
  • [ 374554-56-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; acetic acid; REFERENCE EXAMPLE 32 To a solution of <strong>[374554-54-8]5-amino-1-chloroisoquinoline</strong> (1.0 g) in acetic acid (5 ml) was added 2,5-dimethoxytetrahydrofuran (0.73 ml), and the resultant mixture was heated to 100 C. for an hour. The mixture was evaporated to dryness. The residue was taken up into a mixture of dichloromethane and an aqueous potassium carbonate solution (10%). The separated organic layer was evaporated under reduced pressure. The residue was purified by a column chromatography on silica gel (50 ml) eluding with 0-2% methanol in dichloromethane. The obtained product was triturated with methanol to give 1-chloro-5-(pyrrol-1-yl)isoquinoline (0.55 g). APCI-mass; 229 (m/z, [M+H]+), NMR (DMSO-d6, delta): 6.38 (2H, t, J=2.1 Hz), 7.17 (2H, t, J=2.1 Hz), 7.54 (1H, dd, J=0.8, 5.9 Hz), 7.91 (2H, dd, J=0.8, 4.8 Hz), 8.2-8.4 (2H, m).
  • 9
  • [ 374554-54-8 ]
  • Br(1-)*C9H5ClN3(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide; sodium nitrite; In water; at -5 - 2℃; for 0.583333h; To a 500 mL round-bottomed flask containing l-chloroisoquinolin-5 -amine (Step 2, 5.8 g, 32.5 mmol) in H2O (33 mL) and 40% HBr (14 mL) chilled to -5 OC in an ice bath, was added a freshly prepared solution of (Sodium nitrate (2.47 g, 35.7 mmol) in 8mL OfH2O) drop-wise over 15 minutes. After the addition, the mixture was kept at 2 0C, while stirred an additional 20 minutes. Then urea (0.192 g, 3.2 mmol) was added in order to decompose excess nitrate in the reaction mixture. After an additional 5 minutes of stirring the diazonium salt mixture was transferred into a dropping funnel. The diazonium salt was added drop-wise into a heated (70 0C) solution of Copper (1) Bromide (4.66g, 32.5 mmol) in 40% HBr (30 mL)). After the addition, the mixture was heated to 80 0C for 1.5 hours. Then the mixture was allowed to cool to ambient temperature. The solid, which had formed in the reaction mixture, was collected by filtration. Then recrystallized from hot EtOAc and Hexanes, after drying, gave a brown crystalline solid, which was titled product (4.576 g, 18.9 mmol). MS (ESI pos. ion) m/z: 243 (M+H). Calc'd Exact Mass for C9H5NBrCl: 242.5
  • 10
  • [ 374554-54-8 ]
  • [ 1388846-21-6 ]
  • [ 1885-14-9 ]
  • [ 1401077-66-4 ]
YieldReaction ConditionsOperation in experiment
75% Example 136 1-(1-chloroisoquinolin-5-yl)-3-[(1R,3S)-3-phenylcyclopentyl]urea To a solution of <strong>[374554-54-8]5-amino-1-chloroisoquinoline</strong> (1.00 g, 5.60 mmol) in acetonitrile (25 mL) at room temperature was added pyridine (0.14 mL, 1.7 mmol) followed by phenyl chloroformate (0.70 mL, 5.6 mmol). After 15 minutes, Example 1E (0.903 g, 5.60 mmol) and N,N-diisopropylethylamine (3.9 mL, 22.4 mmol) were added and stirring continued for 15 minutes, followed by the addition of water. The solid was collected by filtration, washed with water then ether, and dried in a vacuum oven at 50 C. to provide the title compound (1.53 g, 75%). 1H NMR (300 MHz, DMSO-d6) delta 8.66 (s, 1H), 8.46-8.28 (m, 2H), 8.03-7.86 (m, 2H), 7.73 (t, J=8.1 Hz, 1H), 7.38-7.09 (m, 5H), 6.82 (d, J=7.2 Hz, 1H), 4.16 (dd, J=13.7, 6.8 Hz, 1H), 3.20-2.98 (m, 1H), 2.44 (dd, J=12.9, 6.6 Hz, 1H), 2.19-1.93 (m, 2H), 1.86-1.59 (m, 2H), 1.59-1.39 (m, 1H). MS (DCI/NH3) m/z 366 [M+H]+.
  • 11
  • [ 374554-54-8 ]
  • [ 222734-73-8 ]
  • 3-(1-chloroisoquinolin-5-yl)-1-methyl-1-(3-(methylthio)phenyl)guanidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% General procedure: S7 (0.35 g, 2 mmol) was dissolved in Et2O (5 mL) and converted into its hydrochloride salt by drop-wise addition of aq. HCl (1 M) in Et2O. The resulting precipitate was collected byfiltration, dried for 10 min, and used in the subsequent reaction. A mixture of S7 hydrochloride (212 mg, 1 mmol), S1 (185 mg, 1.1 mmol), and toluene (2 mL) was heated to 130 oC,stirred for 21 h, cooled to rt, and diluted with MeOH (5 mL). This solution was concentrated onto silicagel and purified on a silica gel column with gradient elution (EtOAc EtOAc-MeOH;4: 1 v/v). The fractions containing the desired guanidine were collected, concentrated under reduced pressure, andapplied to a second silica gel column eluted with Et3N-EtOAc-hexanes(5: 20: 75 by vol.) to afford 20 asa white solid
  • 12
  • [ 374554-54-8 ]
  • [ 433969-27-8 ]
  • C21H23N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
240 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 1.5h;Inert atmosphere; To a solution of compound A20 (300 mg, 1.68 mmol) and compound A19 (506 mg, 2.02 mmol) in dioxane (5 mL) and H20 (1 mL) was added CS2CO3 (547 mg, 1.68 mmol), Pd(dppf)Cl2 (123 mg, 0.168 mmol) under N2. The resulting mixture was heated at l00C and stirred for 1.5 hours to give black suspension. LCMS and TLC showed the reaction was completed. The reaction mixture was quenched by addition H20 (50 mL) and extracted with EtOAc (50 mL x 2). The combined organic layers were washed with brine (20 mL x 2), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by combi flash to give compound A21 (240 mg) as a yellow solid.
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