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[ CAS No. 1197956-03-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1197956-03-8
Chemical Structure| 1197956-03-8
Chemical Structure| 1197956-03-8
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Product Details of [ 1197956-03-8 ]

CAS No. :1197956-03-8 MDL No. :MFCD30303983
Formula : C9H14NO2P Boiling Point : -
Linear Structure Formula :- InChI Key :XSUFWLZYYKQQRC-UHFFFAOYSA-N
M.W : 199.19 Pubchem ID :67052699
Synonyms :

Calculated chemistry of [ 1197956-03-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.31
TPSA : 62.13 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) : -7.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 0.24
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 1.09
Consensus Log Po/w : 1.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.44
Solubility : 7.3 mg/ml ; 0.0367 mol/l
Class : Very soluble
Log S (Ali) : -1.1
Solubility : 15.6 mg/ml ; 0.0785 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.217 mg/ml ; 0.00109 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.07

Safety of [ 1197956-03-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1197956-03-8 ]

* 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 [ 1197956-03-8 ]

[ 1197956-03-8 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 1374641-74-3 ]
  • [ 1197956-03-8 ]
  • [ 1407520-09-5 ]
YieldReaction ConditionsOperation in experiment
58% With potassium phosphate;palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 120.0℃;Sealed tube; Step 1 : Synthesis of 21Compound 19 (1 54mg, 0.54mmol) and compound 20 (107mg, 0.54mmol) were dissolved in 4 mL anhydrous DMF in a sealed tube and was added Pd(OAc)2 ( 14mg, 0.062mmol), XantPhos (37mg, 0.064mmol), and 3P04 (150mg, 0.71 mmol). The content was heated at 120 C overnight. After cooling to the room temp, EtOAc was added and the mixture was filtered through celite, washed with more EtOAc. Combined filtrate was cone in vacuo, and the residue was purified by CombiFlash (MeOH/DCM). The product 21 (140 mg, yield 58%) was obtained as an orange solid.
  • 2
  • [ 76661-24-0 ]
  • [ 1197956-03-8 ]
  • [ 1407520-09-5 ]
YieldReaction ConditionsOperation in experiment
58% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 120.0℃;Sealed tube; Compound 19 (154mg, 0.54mmol) and compound 20 (107mg, 0.54mmol) were dissolved in 4 mL anhydrous DMF in a sealed tube and was added Pd(OAc)2 (14mg, 0.062mmol), XantPhos (37mg, 0.064mmol), and K3PO4 (150mg, 0.71 mmol). The content was heated at 120 C overnight. After cooling to the room temp, EtOAc was added and the mixture was filtered through celite, washed with more EtOAc. Combined filtrate was cone in vacuo, and the residue was purified by CombiFlash (MeOH/DCM). The product 21 (140 mg, yield 58%) was obtained as an orange solid.
  • 3
  • [ 700810-97-5 ]
  • [ 1197956-03-8 ]
  • N-[4-(dimethylphosphoryl)-2-methoxyphenyl]-2-methyl-N'-phenylpyrimidine-4,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; N,N-dimethyl-formamide; at 140.0℃;Sealed tube; N-[4-(dimethylphosphoryl)-2-methoxyphenyl]-2-methyl-N′-phenylpyrimidine-4,6-diamine (0609) To a solution of 6-chloro-2-methyl-N-phenylpyrimidin-4-amine (0.35 mmol) and 4-(dimethylphosphoryl)-2-methoxyaniline (60 mg, 0.30 mmol) in 1 mL of DMF, is added 0.36 mL of 2.5M HCl in Ethanol. The reaction mixture can be heated in a sealed tube at 140 degrees until formation of the desired compound. The reaction mixture is filtered through a syringe filter and can be purified by Prep-HPLC.
  • 4
  • [ 1197956-03-8 ]
  • 6-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyridazin-4-amine [ No CAS ]
  • N3-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N5-[2-(propan-2-ylsulfonyl)phenyl]pyridazine-3,5-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; 2-methoxy-ethanol; at 140.0℃;Sealed tube; N3-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N5-[2-(propan-2-ylsulfonyl)phenyl]pyridazine-3,5-diamine (0612) To a solution of 6-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyridazin-4-amine (0.02 mmol) and 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 72:15 mg, 0.7 mmol) in 1 mL of 2-Methoxy ethanol, is added 1 mL of 2.5M HCl in Ethanol. The reaction mixture is heated in a sealed tube at 140 degree until formation of the desired compound. The reaction mixture is filtered through a syringe filter and can be purified by Prep-HPLC.
  • 5
  • [ 1197956-03-8 ]
  • 3-chloro-5-[3-fluoro-5-(trifluoromethyl)phenoxy]pyridazine [ No CAS ]
  • N-[4-(dimethylphosphoryl)-2-methoxyphenyl]-5-[3-fluoro-5-(trifluoromethyl)phenoxy]pyridazin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; 2-methoxy-ethanol; at 140.0℃;Sealed tube; N-[4-(dimethylphosphoryl)-2-methoxyphenyl]-5-[3-fluoro-5-(trifluoromethyl) phenoxy]pyridazin-3-amine (0615) To a solution of 3-chloro-5-[3-fluoro-5-(trifluoromethyl)phenoxy]pyridazine (0.02 mmol) and 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 72:15 mg, 0.7 mmol) in 1 mL of 2-Methoxy ethanol, is added 1 mL of 2.5M HCl in Ethanol. The reaction mixture is heated in a sealed tube at 140 degree until formation of the desired compound. The reaction mixture is filtered through a syringe filter and can be purified by Prep-HPLC.
  • 6
  • [ 1197956-03-8 ]
  • 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyridin-4-amine [ No CAS ]
  • N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyridine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; 2-methoxy-ethanol; at 90.0℃;Sealed tube; N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl] pyridine-2,4-diamine (0632) To a solution of 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyridin-4-amine (0.12 mmol) in 1 mL of 2-methoxyethanol is added 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 72: 0.12 mmol) and 49 μL of 2.5 M HCl in ethanol. The mixture is heated in a sealed tube at 90 C. until formation of the desired compound. The mixture is then basified with 1N NaOH solution, and extracted with ethyl acetate. The organic layers can be combined, washed with saturated sodium chloride solution, dried with sodium sulfate, filtered and concentrated. The crude residue can be purified by prep-HPLC to afford the final compound.
  • 7
  • [ 1197956-03-8 ]
  • [ 83403-50-3 ]
  • 6-chloro-N3-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N5-phenyl-1,2,4-triazine-3,5-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With camphor-10-sulfonic acid; In dichloromethane; isopropyl alcohol; 6-chloro-N3-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N5-phenyl-1,2,4-triazine-3,5-diamine (0720) A mixture of 3,6-dichloro-N-phenyl-1,2,4-triazin-5-amine (1 mmol), 4-(dimethylphosphoryl)-2-methoxyaniline (1 mmol) and camphorsulfonic acid (0.7equiv.), is refluxed for 20-48 h in 2-propanol. The reaction mixture is allowed to cool to room temperature, dissolved in dichloromethane and washed with an aqueous solution of Na2CO3. The dichloromethane extract is dried over MgSO4 and evaporated. The crude product is purified by Prep-HPLC.
  • 8
  • [ 1197956-03-8 ]
  • 3,6-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazin-5-amine [ No CAS ]
  • 6-chloro-N3-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N5-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazine-3,5-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With camphor-10-sulfonic acid; In isopropyl alcohol;Reflux; 6-chloro-N3-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N5-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazine-3,5-diamine (0723) A mixture of 3,6-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazin-5-amine (1 mmol), 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 105: 1 mmol) and camphorsulfonic acid (0.7 equiv.), is refluxed for 20-48 hours in 2-propanol. The reaction mixture is allowed to cool to room temperature, dissolved in dichloromethane and washed with an aqueous solution of Na2CO3. The dichloromethane extract is dried over MgSO4 and evaporated. The crude product is purified by Prep-HPLC.
  • 9
  • [ 1197956-03-8 ]
  • 3,6-dichloro-5-[3-fluoro-5-(trifluoromethyl)phenyl]sulfanyl}-1,2,4-triazine [ No CAS ]
  • 6-chloro-N-[4-(dimethylphosphoryl)-2-methoxyphenyl]-5-[3-fluoro-5-(trifluoromethyl)phenyl]sulfanyl}-1,2,4-triazin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With camphor-10-sulfonic acid; In isopropyl alcohol;Reflux; 6-chloro-N-[4-(dimethylphosphoryl)-2-methoxyphenyl]-5-[3-fluoro-5-(trifluoromethyl)phenyl]sulfanyl}-1,2,4-triazin-3-amine (0726) A mixture of 3,6-dichloro-5-[3-fluoro-5-(trifluoromethyl)phenyl]sulfanyl}-1,2,4-triazine (0.7 mmol), 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 105: 15 mg, 0.7 mmol) and camphorsulfonic acid (0.7 equiv.), is refluxed for 20-48 hours in 2-propanol. The reaction mixture is allowed to cool to room temperature, dissolved in dichloromethane and washed with an aqueous solution of Na2CO3. The dichloromethane extract is dried over MgSO4 and evaporated. The crude product is purified by Prep-HPLC.
  • 10
  • [ 1197956-03-8 ]
  • [ 280581-45-5 ]
  • 5-chloro-N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-phenylpyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With hydrogenchloride; In ethanol; N,N-dimethyl-formamide; at 140.0℃;Sealed tube; 5-chloro-N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-phenylpyrimidine-2,4-diamine (0435) To a solution of 2,5-dichloro-N-phenylpyrimidin-4-amine (84 mg, 0.35 mmol) and 4-(dimethylphosphoryl)-2-methoxyaniline (60 mg, 0.30 mmol) in 1 mL of DMF, was added 0.36 mL of 2.5M HCl in Ethanol. The reaction mixture was heated in a sealed tube at 140 degrees over night. The reaction mixture was filtered through a syringe filter and purified by Prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases) to yield the desired product as a white solid. (23 mg, 16% yield). MS/ES+: m/z=403
  • 11
  • [ 6627-53-8 ]
  • [ 1197956-03-8 ]
  • 12
  • (3-methoxy-4-nitrophenyl)(dimethyl)phosphane oxide [ No CAS ]
  • [ 1197956-03-8 ]
YieldReaction ConditionsOperation in experiment
78% With acetic acid; zinc; In methanol; at 20.0℃; for 2.0h; A mixture of intermediate 220 (334.00 mg, 1.46 mmol), zinc (953.00 mg, 14.60 mmol)and AcOH (0.83 mL, 14.60 mmol) in MeOH (8 mL) was stirred at rt for 2 h. Themixture was filtered on a pad of celite then an extraction was performed with EtOAc and HC1 iN. The aqueous layer was basified with NaOH iN and extracted with EtOAc (10 times). The organic layers were washed with brine, dried with MgSO4 and evaporated to give 226 mg of intermediate 221 (78% yield, brown oil).
  • 13
  • [ 1197956-03-8 ]
  • 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]-5-(trifluoromethyl)pyrimidin-4-amine [ No CAS ]
  • N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-5-(trifluoromethyl)pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% With hydrogenchloride; In ethanol; 2-methoxy-ethanol; at 140.0℃;Sealed tube; N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-5-(trifluoromethyl)pyrimidine-2,4-diamine (0438) To a solution of 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]-5-(trifluoromethyl)pyrimidin-4-amine (7.5 mg, 0.02 mmol) and 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 15: 15 mg, 0.7 mmol) in 1 mL of 2-Methoxy ethanol, was added 1 mL of 2.5M HCl in Ethanol. The reaction mixture was heated in a sealed tube at 140 degree over night. The reaction mixture was filtered through a syringe filter and purified by Prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases) to yield the desired product as a white solid. (0.9 mg, 8% yield). MS/ES+: m/z=543
  • 14
  • [ 761440-16-8 ]
  • [ 1197956-03-8 ]
  • 5-chloro-N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With hydrogenchloride; In ethanol; 2-methoxy-ethanol; at 140.0℃; for 1.0h;Sealed tube; 5-chloro-N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine (0441) To a solution of 2,5-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyrimidin-4-amine (0.050 g, 0.14 mmol) in 1 mL of 2-methoxyethanol was added 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 15: 0.029 g, 0.14 mmol) and 0.12 ml of 2.5M HCl in EtOH. The mixture was heated in a sealed tube at 140 C. for 1 h. The mixture was basified with saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was purified by prep-HPLC to give the final product (20 mg, 24% yield). MS/ES+: m/z=508.
  • 15
  • [ 761440-16-8 ]
  • [ 1197956-03-8 ]
  • 5-chloro-N2-[4-(dimethylphosphoryl)phenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With hydrogenchloride; In ethanol; 2-methoxy-ethanol; at 140.0℃; for 1.0h;Sealed tube; Example 18 5-chloro-N2-[4-(dimethylphosphoryl)phenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine (0442) (0443) To a solution of 2,5-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyrimidin-4-amine (prepared as in Example 17: 50 mg, 0.14 mmol) in 1 mL of 2-methoxyethanol was added 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 15: 0.025 g, 0.14 mmol) and 0.12 ml of 2.5M HCl in EtOH. The mixture was heated in a sealed tube at 140 C. for 1 h. The mixture was basified with saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was purified by prep-HPLC to give the final product (0.100 g, 15% yield). MS/ES+: m/z=478.
  • 16
  • [ 1197956-03-8 ]
  • 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]-5-(trifluoromethyl)pyridin-4-amine [ No CAS ]
  • N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-5-(trifluoromethyl)pyridine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; 2-methoxy-ethanol; at 90.0℃;Sealed tube; To a solution of 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]-5-(trifluoromethyl)pyridin-4-amine (0.12 mmol) in 1 mL of 2-methoxyethanol is added 4-(dimethylphosphoryl)-2-methoxyaniline (prepared as in Example 72: 0.12 mmol) and 49 μL of 2.5 M HCl in ethanol. The mixture is heated in a sealed tube at 90 C. until formation of the desired compound. The mixture is then basified with 1N NaOH solution, and extracted with ethyl acetate. The organic layers can be combined, washed with saturated sodium chloride solution, dried with sodium sulfate, filtered and concentrated. The crude residue can be purified by prep-HPLC to afford the final compound.
  • 17
  • [ 1042434-76-3 ]
  • [ 1197956-03-8 ]
  • 2-((5-chloro-2-((4-(dimethylphosphoryl)-2-methoxyphenyl)amino)pyrimidin-4-yl)amino)benzamide [ No CAS ]
  • 18
  • [ 1197956-03-8 ]
  • C12H9Cl2N3O [ No CAS ]
  • 1-(2-((5-chloro-2-((4-(dimethylphosphoryl)-2-methoxyphenyl)amino)pyrimidin-4-yl)amino)phenyl)ethan-1-one [ No CAS ]
  • 19
  • [ 1197956-03-8 ]
  • C11H9Cl2N3O2S [ No CAS ]
  • (4-((5-chloro-4-((2-(methylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-3-methoxyphenyl)dimethylphosphine oxide [ No CAS ]
  • 20
  • [ 1022962-03-3 ]
  • [ 1197956-03-8 ]
  • (4-((5-chloro-4-((2-methoxyphenyl)amino)pyrimidin-2-yl)amino)-3-methoxyphenyl)dimethyl-phosphine oxide [ No CAS ]
  • 21
  • [ 1197956-03-8 ]
  • [ 1197953-49-3 ]
  • (2-((5-chloro-2-((4-(dimethylphosphoryl)-2-methoxyphenyl)amino)pyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide [ No CAS ]
  • 22
  • [ 59557-91-4 ]
  • [ 7211-39-4 ]
  • [ 1197956-03-8 ]
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