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[ CAS No. 872511-32-5 ] {[proInfo.proName]}

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Chemical Structure| 872511-32-5
Chemical Structure| 872511-32-5
Structure of 872511-32-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 872511-32-5 ]

CAS No. :872511-32-5 MDL No. :MFCD26398647
Formula : C9H7Cl2NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VJFDWELAHZSVEE-UHFFFAOYSA-N
M.W : 248.06 Pubchem ID :86086993
Synonyms :

Calculated chemistry of [ 872511-32-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.23
TPSA : 47.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 3.92
Log Po/w (WLOGP) : 2.98
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 3.35
Consensus Log Po/w : 2.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.95
Solubility : 0.0281 mg/ml ; 0.000113 mol/l
Class : Soluble
Log S (Ali) : -4.62
Solubility : 0.00589 mg/ml ; 0.0000237 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.88
Solubility : 0.0324 mg/ml ; 0.000131 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.31

Safety of [ 872511-32-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P305+P351+P338-P342+P311 UN#:2811
Hazard Statements:H302-H312-H315-H319-H332-H334-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 872511-32-5 ]

* 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 [ 872511-32-5 ]

[ 872511-32-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 75-44-5 ]
  • [ 872509-56-3 ]
  • [ 872511-32-5 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; toluene; at 20 - 100℃; for 1 - 6h;Product distribution / selectivity; Example 2: 3-(2.6-Dichloro-3.5-dimethoxv-phenyl)-1-methyl-1-(6-f4-(4-methvl-piperazin-1-vl)-phenvlamino1-pyrimidin-4-vl>-ureaTo a solution of <strong>[872509-56-3]2,6-dichloro-3,5-dimethoxyaniline</strong> (preparation 2, 74 mg, 0.34 mmol, 1.25 eq.) in dioxane is added 20% phosgene solution in toluene (191 i, 0.36 mmol, 1.35 eq.) under argon. The reaction mixture is stirred for further 6h at room temperature under argon. Then, the solvent is evaporated and the colorless crystalline residue is taken up in dry toluene (2.5 ml). After the addition of A/-methyl-A/'-[4-(4-methyl-piperazin-1-yl)-phenyl]-pyrimidine-4,6-diamine (see example 1, 80 mg, 0.27 mmol, 1.0 eq.) the suspension is stirred at 70C for 36h under argon. After cooling the precipitate is filtered off, washed with toluene, methanol/ether 1:1, and ether to give a beige powder. The crude product is purified by flash chromatography (1% MeOH in DCM to 16% MeOH in DCM within 30 min). The fractions containing the product are pooled, evaporated, and triturated with ether. The precipitate is filtered off, washed (1x cold methanol/ether 1:1, 1x ether), and vacuum dried at 45C overnight to afford the title compound as colorless powder: m.p. 221 C (dec.), ESI-MS:546.1/548.0/550.0 [MH]+.; Example 227: 3-(2.6-Dichloro-3.5-dimethoxv-phenyl)-1 -methvl-1 -{4-[4-(4-methyl-piperazin-1 -vl)-phenvlaminoH1,3.51triazin-2-vl}-ureaTo a solution of 2,6-dichloro-3,5-dimethoxy-aniIine (124 mg , 0.56 mmol; Preparation 2) in 2ml of dioxane under a nitrogene atmosphere, phosgene (0.52 ml 20 % in toluene, 0.98mmol) is added. The mixture is stirred for 70 min at 100 C, cooled to RT and concentratedin vacuo, yielding 2,6-dichloro-3,5-dimethoxyphenylisocyanate.The resulting solid is added portion-wise to a boiling solution of N-methyl-N'-[4-(4-methyl-piperazin-1-yl)-phenyl]-[1,3,5]triazine-2,4-diamine (140 mg, 0.47 mmol) in 8 ml of tolueneduring 20 min. After 3 h, another 2 eq of 2,6-dichloro-3,5-dimethoxyphenylisocyanate areadded and stirring is continued for totally 5 h. Then the reaction mixture is diluted with DCMand a saturated aqueous solution of NaHCO3. The aqueous layer is separated and extractedtwice with DCM. The organic phases are washed with water and brine, dried (Na2SO4) andconcentrated. Column chromatography (SiO2; DCM/MeOH/NH3aq 97:3:0.2) gives the titlecompound: ESI-MS: 547 / 549 [MH]+; tR= 3.5 min (purity: 100%, gradient J); TLC: Rf = 0.40(DCM/MeOH + 1 % NH3aq, 95:5).; Example 228: 3-(2.6-Dichloro-3.5-dimethoxv-phenyl)-1 -methyl-1 -|4-f4-(4-ethyl-piperazin-1 -vn-phenvlaminoW1.3.51triazin-2-vl)-ureaTo a solution of 2,6-dichloro-3,5-dimethoxy-anilin (133 mg , 0.60 mmol; Preparation 2) in 2ml of dioxane under a nitrogen atmosphere, phosgene ( 0.54 ml 20 % in toluene, 1.0 mmol)is added. The mixture is stirred for 60 min at 100 C, cooled to RT and concentrated invacuo, yielding 2,6-dichloro-3,5-dimethoxyphenylisocyanate.The resulting solid is added portion-wise to a boiling solution of N-methyl-N'-[4-(4-ethyl-piperazin-1-yl)-phenyl]-[1,3,5]triazine-2,4-diamine (156 mg, 0.50 mmol) in 7 ml of tolueneduring 15 min. After 5 h, the reaction mixture is diluted with DCM and a saturated aqueoussolution of NaHCO3. The aqueous layer is separated and extracted twice with DCM. Theorganic phases are washed with water and brine, dried (Na2SO4) and concentrated. Columnchromatography (SiO2; DCM/MeOH/NH3aq 95:5:0.2) gives the title compound: ESI-MS: 561 /563 [MH]*; tR= 3.6 min (gradient J); TLC: Rf = 0.4 (DCM/MeOH + 1 % NH3aq, 95:5).
In 1,4-dioxane; toluene; for 1h;Heating / reflux;Product distribution / selectivity; 1-(2,6-Dichloro-3,5-dimethoxy-phenyl)-3-f6-r4-f2-morpholin-4-yl-ethoxy)- phenylaminoi-pyrimidin-4-yll-ureaPhosgene (20% in toluene, 0.8 ml_, 1.58 mmol, 2.4 equiv) is added to a solution of 2,6- dichloro-3,5-dimethoxyaniline (175 mg, 0.79 mmol, 1.2 equiv) in dioxane (2.5 ml_), under an <n="69"/>argon atmosphere. The mixture is heated to reflux, stirred for 1 h, allowed to cool to RT, and concentrated in vacuo. The resulting isocya?ate is added to a solution of N-[4-(2-morpholin- 4-yl-ethoxy)-phenyl]-pyrimidine-4,6-diamine (208.5 mg, 0.66 mmol) in NMP (2 ml_), at 75C and under an argon atmosphere. The reaction mixture is stirred at 750C for 2h, allowed to cool to RT, and is then diluted with DCM and a saturated aqueous solution of NaHCO3. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the crude product by silica gel column chromatography (DCM/MeOH + 1 % NH3aq, 96:4), followed by trituration of the resulting material in MeOH, affords the title compound as a white solid: ESI-MS: 562.9 / 564.9 [MH]+; tR= 2.99 min (purity: 100%, system 1); TLC: R, = 0.36 (DCM/MeOH + 1 % NH3aq, 93:7).; 3-(2,6-Dichloro-3.5-cJimethoxy-phenyl)-1 -methyl-1 -f6-r3-(4-methyl-piperazin-1 - ylmethyl)-phenylamino1-pyrimidin-4-yl)-ureaPhosgene (20% in toluene, 1 ml_, 2.0 mmol, 2.4 equiv) is added to a solution of 2,6-dichloro- 3,5-dimethoxyaniline (221 mg, 1.0 mmol, 1.2 equiv) in dioxane (2.5 ml_), under an argon atmosphere. The mixture is heated to reflux, stirred for 1h, allowed to cool to RT, and concentrated in vacuo. The resulting isocyanate is added to a solution of N-methyl-N'-[3-(4- methyl-piperazin-1-ylmethyl)-phenyl]-pyrimidine-4,6-diamine (Step 2.1) (259 mg, 0.83 mmol) Jn toluene (5 ml_), at reflux and under an argon atmosphere. The reaction mixture is stirred at reflux for 3h, allowed to cool to RT1 and diluted with DCM and a saturated aqueous solution of NaHCO3. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the crude product by silica gel column chromatography (DCM/MeOH + 1 % NH3aq, 95:5) affords the title compound as a yellow solid: ESI-MS: 560.0 / 562.0 [MHf; tR= 3.26 min (purity: 99%, system 1); TLC: R, = 0.37 (DCM/MeOH + 1 % NH3aq, 9:1 ).
  • 3
  • [ 872511-32-5 ]
  • [ 1702259-66-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 2 h / 0 - 20 °C 2.1: hydrogen / tetrahydrofuran; methanol; water / 3 h / -10 °C / 760.05 Torr 3.1: tetrahydrofuran / 1 h / -10 °C
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 2 h / 0 - 20 °C 2.1: hydrogen / tetrahydrofuran; water; methanol / 3 h / 20 °C / 760.05 Torr 3.1: tetrahydrofuran / 1 h / -10 °C
  • 4
  • [ 872511-32-5 ]
  • [ 61667-16-1 ]
  • [ 76513-69-4 ]
  • 1-benzyl-1-(6-chloropyrimidin-4-yl)-3-(2,6-dichloro-3,5-dimethoxyphenyl)-3-(2-trimethylsilanyl-ethoxymethyl)-urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: benzyl-(6-chloropyrimidin-4-yl)-amine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.166667h; Stage #2: 2,4-dichloro-3-isocyanato-1,5-methoxy-4-methylbenzene In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #3: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; 130.b b. l-Benzyl-l-(6-chloro-pyrimidin-4-yl)-3-(2,6-dichhrO'3,5'dim trimethylsilanyl~ethoxymethyl)-urea b. l-Benzyl-l-(6-chloro-pyrimidin-4-yl)-3-(2,6-dichhrO'3,5'dim trimethylsilanyl~ethoxymethyl)-urea To a solution of benzyl"(6-chloro-pyrimidin-4-yl)-amine (800 mg, 3,64 mmol) in DMF (15 mL) was added NaH (60%, 218 mg, 5.45 mmol) at 0 °C, and the mixture was stirred for 10 minutes at room temperature. A solution of l-isocyanato-3,5-dimethoxy-benzene (Procedure 2A , steps a-d; 1.35 g, 5.45 mmol) in DMF (2 mL) was added dropwise at 0 °C. The resulting mixture was stirred at room temperature for 2 hours. Saturated aqueous NH4CI (2 mL) was added to quench the reaction. The mixture was concentrated and extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2S04, and concentrated to give the crude product, which was purified by flash chromatography on silica to obtain the title compound (1.7 g, yield: 77%). MS (ESI): 599 [M+H]+.
  • 5
  • [ 872509-56-3 ]
  • [ 32315-10-9 ]
  • [ 872511-32-5 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; In 1,4-dioxane; at 130℃; for 2h;Microwave irradiation; d. 2, 4-Dichloro-3-isocyanafo-l, 5-dimethoxy-benzene A mixture of 2,6-dichioro- 3,5-dimethoxy-phenylamine (500 mg, 2.25 mmol), triphosgene (335 mg, 1.12 mmol) and TEA (342 mg, 3.38 mmol) in dioxane (15 mL) was heated to 130 C for 2 hours under microwave. The reaction was concentrated and the residue was purified by flash chromatography on silica eiuting with DCM to obtain the title compound (450 mg, yield: 80%). 1H-NMR (400 MHz, CDC13) delta 3.92 (s, 6H), 6.42 (s, 1H).
80% With triethylamine; In 1,4-dioxane; at 130℃; for 2h;Microwave irradiation; A mixture of 2,6-dichloro- 3,5-dimethoxy-phenylamine (500 mg, 2.25 mmol), triphosgene (335 mg, 1.12 mmol) and TEA (342 mg, 3.38 mmol) in dioxane (15 mL) was heated to 130 C for 2 hours under microwave. The reaction was concentrated and the residue was purified by flash chromatography on silica eluting with DCM to obtain the title compound (450 mg, yield: 80%). 1H-NMR (400 MHz, CDC13) delta 3.92 (s, 6H), 6.42 (s, 1H).
56.4% With triethylamine; In 1,4-dioxane; at 130℃; for 3h;Microwave irradiation; 2,6-Dichloro-3,5-dimethoxyaniline (0.5 g, 2.3 mmol) was dissolved in 1,4-dioxane (8 mL).Triphosgene (333.8 mg, 1.15 mmol) and triethylamine (341.5 mg, 3.45 mmol) were added in that order.The microwave was reacted at a temperature of 130 C for 3 hours. The reaction solution was concentrated and dissolved in EA.Column chromatography on silica gel (PE:EA=5:1Flash elution) gave a yellow solid (321.7 mg, yield: 56.4%)
In 1,4-dioxane; at 100℃; for 3.5h; A 3 L 3-necked round bottom flask was charged with <strong>[872509-56-3]2,6-dichloro-3,5-dimethoxyaniline</strong> (199.65g, 899 mmol), triphosgene (93g, 315 mmol, 0.35 equiv), and 1 ,4-dioxane (1.9 L). The mixture was heated to 100 C and stirred at this temperature for 3.5 h. The mixture was then cooled to 20-25 C, and filtered. The solid residue was washed with 1,4-dioxane (200 mL). The filtrate was concentrated to a minimal stirrable volume and chased 3x with dioxane (700 mL each chase). The solution was concentrated to a minimal stirrable volume following the last chase and then redissolved in 1,4-dioxane (730 mL). To this slurry was charged 6-chloro-N- methylpyrimidin-4-amine (129g, 899 mmol, 1 equiv). The resulting mixture was heated to 80 C and stirred at this temperature for 60 h, during which time a substantial amount of precipitate formed. The mixture was cooled to 20-22 C and filtered. The solid cake was washed with dioxane (2 x 90 mL) and dried under vacuum at room temperature with a nitrogen sweep to afford the title compound (191g, 54% yield) as a solid.
With triethylamine; In 1,4-dioxane; at 130℃; for 2h; In a 500 mL single-necked flask, 1,4-dioxane (200 mL) was added, followed by <strong>[872509-56-3]2,6-dichloro-3,5-dimethoxyaniline</strong> (11 g), triphosgene (8.86 g) and Triethylamine (4.02 g) was reacted at 130 C for 2 h. TLC showed the reaction was completed, and the solvent was evaporated to give a crude material
In 1,4-dioxane; at 110℃; for 2h; Compound 1l (221 mg, 1.0 mmol) and triphosgene (298 mg, 1.0 mmol) were added to 10 mL of anhydrous 1,4-dioxane at room temperature with stirring. The reaction mixture was heated to 110C. for two hours. After the reaction was completed, it was cooled to room temperature and concentrated under reduced pressure to give compound 1m (230 mg, crude) as a pale yellow solid. The crude product was used in the next reaction without further purification.

  • 6
  • [ 872511-32-5 ]
  • [ 941294-43-5 ]
  • 1-(6-chloropyrimidin-4-yl)-1-cyclopropyl-3-(2,6-dichloro-3,5-dimethoxyphenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.6% Stage #1: 6-chloro-N-cyclopropylpyrimidin-4-amine With sodium hydride In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: 2,4-dichloro-3-isocyanato-1,5-methoxy-4-methylbenzene 1.5 1-(6-chloropyrimidin-4-yl)-1-cyclopropyl-3-(2,6-dichloro-3,5-dimethoxyphenyl)urea Cyclopropylpyrimidin-4-amine 1h (800 mg, 4.72 mmol) was dissolved in 15 mL N, N- dimethylformamide and 60% sodium hydride (377.3 mg, 9.43 mmol) was dissolved in 5 mL N , N-dimethylformamide, and the mixture was stirred for 30 minutes in an ice bath.Chloro-3-isocyanato-1,5-methoxy-4-methylbenzene 1i (2.00 g, 8.17 mmol) was dissolved in 10 mL of N, N-dimethylformamide dropwise into the reaction solution, The reaction was carried out for 0.5 hour at room temperature.The reaction was quenched by the addition of 40 mL of saturated ammonium chloride solution, and then 50 mL of ethyl acetate and 50 mL of water were added. The layers were separated and the aqueous phase was extracted with ethyl acetate (20 mL x 3). The organic phases were combined and concentrated under reduced pressure to afford crude 1 (6-chloropyrimidin-4-yl) -1-cyclopropyl-3- (2,6-dichloro-3,5-dimethoxyphenyl) urea 1j (1.45 g, white solid) Yield: 73.6%
  • 7
  • [ 872511-32-5 ]
  • [ 776-53-4 ]
  • C15H12Cl2N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.77 g At 0 C., sodium hydride (0.23 g) was added portionwise to a solution of compound 134 (0.94 g) in DMF (20 mL) and stirred for 10 minutes, then compound 135 (0.81 g) was added, and then raised to room temperature and stirred for 6 hours, The mixture was poured into water, extracted with ethyl acetate, the extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was separated by silica gel column chromatography (DCM / MeOH = 100/5) to obtain compound 136 (0.77g ).
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