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[ CAS No. 1234616-70-6 ] {[proInfo.proName]}

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Chemical Structure| 1234616-70-6
Chemical Structure| 1234616-70-6
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Product Details of [ 1234616-70-6 ]

CAS No. :1234616-70-6 MDL No. :MFCD17015892
Formula : C7H2BrCl2N3 Boiling Point : -
Linear Structure Formula :- InChI Key :VPAHKVLQMKEPQW-UHFFFAOYSA-N
M.W : 278.92 Pubchem ID :72207616
Synonyms :

Calculated chemistry of [ 1234616-70-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.05
TPSA : 38.67 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) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.23
Log Po/w (XLOGP3) : 3.42
Log Po/w (WLOGP) : 3.09
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 3.39
Consensus Log Po/w : 2.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.29
Solubility : 0.0142 mg/ml ; 0.0000509 mol/l
Class : Moderately soluble
Log S (Ali) : -3.91
Solubility : 0.0341 mg/ml ; 0.000122 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.04
Solubility : 0.00256 mg/ml ; 0.00000916 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.73

Safety of [ 1234616-70-6 ]

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

Application In Synthesis of [ 1234616-70-6 ]

* 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 [ 1234616-70-6 ]

[ 1234616-70-6 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 142168-97-6 ]
  • [ 1234616-70-6 ]
YieldReaction ConditionsOperation in experiment
80% With trichlorophosphate; In N,N-dimethyl-formamide; for 6.0h;Reflux; General procedure: 2,4,6-Trichloro-pyrido[2,3-d]pyrimidine (6) (C7H2Cl3N3): A mixture of 50 mL of POCl3, two drops of DMF, and 5 g of 6-chloro-1H-pyrido[2,3-d]pyrimidine-2,4-dione 4 were heated to reflux. After 6 h, the reaction was evaporated under reduced pressure; 400 mL of CH2Cl2 and 20 mL of water were added to the residue at C. The aqueous phase was extracted, the organic layers were combined and then dried over magnesium sulfate. After filtration the filtrate was evaporated under reduced pressure, and then washed with Et2O to obtain compound 6 as a yellow solid in 64% yield.
  • 2
  • methyl 5-bromo-2-(3-(2,2,2-trichloroacetyl)ureido)nicotinate [ No CAS ]
  • [ 1234616-70-6 ]
  • 3
  • [ 50735-34-7 ]
  • [ 1234616-70-6 ]
  • 4
  • [ 142168-97-6 ]
  • [ 1234616-70-6 ]
YieldReaction ConditionsOperation in experiment
64% With N,N-diethylaniline; trichlorophosphate; at 110.0℃; for 5.0h; Prepared from13 (1.02?g, 4.23?mmol) by general procedure C. Yellow solid (755.1?mg, 64%). 1H NMR (CDCl3) delta?=?8.75 (d, 1H, J?=?2.5?Hz), 9.30 (d, 1H, J?=?2.5?Hz). MS (ESI) 279.8 (M+H)+.
  • 5
  • [ 1234616-70-6 ]
  • tert-butyl ((1s,4s)-4-((6-bromo-2-(isopropylamino)pyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate [ No CAS ]
  • 6
  • [ 1234616-70-6 ]
  • tert-butyl ((1S,4s)-4-((6-bromo-2-(((R)-1-hydroxypropan-2-yl)amino)pyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate [ No CAS ]
  • 7
  • [ 1234616-70-6 ]
  • tert-butyl ((1s,4s)-4-((6-(3-fluorophenyl)-2-(isopropylamino)pyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate [ No CAS ]
  • 8
  • [ 1234616-70-6 ]
  • tert-butyl ((1S,4s)-4-((6-(3-fluorophenyl)-2-(((R)-1-hydroxypropan-2-yl)amino)pyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate [ No CAS ]
  • 9
  • [ 1234616-70-6 ]
  • N4-((1s,4s)-4-aminocyclohexyl)-6-(3-fluorophenyl)-N2-isopropylpyrido[2,3-d]pyrimidine-2,4-diamine [ No CAS ]
  • 10
  • [ 1234616-70-6 ]
  • (R)-2-((4-(((1s,4S)-4-aminocyclohexyl)amino)-6-(3-fluorophenyl)pyrido[2,3-d]pyrimidin-2-yl)amino)propan-1-ol [ No CAS ]
  • 11
  • [ 1234616-70-6 ]
  • 1-((1s,4S)-4-((6-(3-fluorophenyl)-2-(isopropylamino)pyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)-3-((R)-1-hydroxy-3-methylbutan-2-yl)urea [ No CAS ]
  • 12
  • [ 1234616-70-6 ]
  • 1-((1S,4S)-4-((6-(3-fluorophenyl)-2-(((R)-1-hydroxypropan-2-yl)amino)pyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)-3-((R)-1-hydroxy-3-methylbutan-2-yl)urea [ No CAS ]
  • 13
  • [ 247570-24-7 ]
  • [ 1234616-70-6 ]
  • tert-butyl ((1s,4s)-4-((6-bromo-2-chloropyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 3h; Prepared from 17 (155.7?mg, 0.558?mmol) and N-Boc-cis-1,4-cyclohexanediamine (144?mg, 0.670?mmol) by general procedure D. Slight yellow solid (275.0?mg, quant.). 1H NMR (CDCl3) delta?=?1.46 (s, 9H), 1.87 (m, 8H), 3.71 (m, 1H), 4.43 (m, 1H), 4.64 (br, 1H), 6.09 (br, 1H), 8.26 (d, 1H, J?=?2.4?Hz), 9.02 (d, 1H, J?=?2.4?Hz). MS (ESI) 456.0 (M+H)+.
  • 14
  • [ 1234616-70-6 ]
  • [ 5720-07-0 ]
  • C21H16ClN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110.0℃; for 3.0h; General procedure: To an argon degassed solution of 6-halogeno-2,4-dichloropyrido[2,3-d]pyrimidine 6 or 7 (0.5 mmol) in toluene (6mL) the desired (Het)aryl boronic acid was added then (1.5 equiv)potassium carbonate and (0.05 equiv) Pd(PPh3)4 were also added.The reaction was stirred at 110C for the desired time. After completion of the reaction, 10 mL of water was added, and then extracted with dichloromethane (3 10 mL), the organic layers were combined and dried using magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained material was purified on silica gel by column chromatography (CH2Cl2/PE: 90/10)to afford compounds 8-12. 2,4-Dichloro-6-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine (8) (C14H9Cl2N3O): Compound 8 was obtained from 2,4,6-trichloropyrido[2,3-d]pyrimidine 6 using 4-methoxyphenyl boronic acid (1.05 equiv), as a white solid in 83%yield.
  • 15
  • [ 1234616-70-6 ]
  • [ 5720-07-0 ]
  • C21H16ClN3O2 [ No CAS ]
  • C14H9BrClN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
36%; 7% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110.0℃; for 3.0h; General procedure: To an argon degassed solution of 6-halogeno-2,4-dichloropyrido[2,3-d]pyrimidine 6 or 7 (0.5 mmol) in toluene (6mL) the desired (Het)aryl boronic acid was added then (1.5 equiv)potassium carbonate and (0.05 equiv) Pd(PPh3)4 were also added.The reaction was stirred at 110C for the desired time. After completion of the reaction, 10 mL of water was added, and then extracted with dichloromethane (3 10 mL), the organic layers were combined and dried using magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained material was purified on silica gel by column chromatography (CH2Cl2/PE: 90/10)to afford compounds 8-12. 2,4-Dichloro-6-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine (8) (C14H9Cl2N3O): Compound 8 was obtained from 2,4,6-trichloropyrido[2,3-d]pyrimidine 6 using 4-methoxyphenyl boronic acid (1.05 equiv), as a white solid in 83%yield.
  • 16
  • [ 55552-70-0 ]
  • [ 1234616-70-6 ]
  • C15H8ClN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110.0℃; for 3.0h; General procedure: To an argon degassed solution of 6-halogeno-2,4-dichloropyrido[2,3-d]pyrimidine 6 or 7 (0.5 mmol) in toluene (6mL) the desired (Het)aryl boronic acid was added then (1.5 equiv)potassium carbonate and (0.05 equiv) Pd(PPh3)4 were also added.The reaction was stirred at 110C for the desired time. After completion of the reaction, 10 mL of water was added, and then extracted with dichloromethane (3 10 mL), the organic layers were combined and dried using magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained material was purified on silica gel by column chromatography (CH2Cl2/PE: 90/10)to afford compounds 8-12. 2,4-Dichloro-6-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine (8) (C14H9Cl2N3O): Compound 8 was obtained from 2,4,6-trichloropyrido[2,3-d]pyrimidine 6 using 4-methoxyphenyl boronic acid (1.05 equiv), as a white solid in 83%yield.
  • 17
  • [ 5345-47-1 ]
  • [ 1234616-70-6 ]
  • 18
  • [ 6165-69-1 ]
  • [ 1234616-70-6 ]
  • C15H8ClN3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110.0℃; for 3.0h; General procedure: To an argon degassed solution of 6-halogeno-2,4-dichloropyrido[2,3-d]pyrimidine 6 or 7 (0.5 mmol) in toluene (6mL) the desired (Het)aryl boronic acid was added then (1.5 equiv)potassium carbonate and (0.05 equiv) Pd(PPh3)4 were also added.The reaction was stirred at 110C for the desired time. After completion of the reaction, 10 mL of water was added, and then extracted with dichloromethane (3 10 mL), the organic layers were combined and dried using magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained material was purified on silica gel by column chromatography (CH2Cl2/PE: 90/10)to afford compounds 8-12. 2,4-Dichloro-6-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine (8) (C14H9Cl2N3O): Compound 8 was obtained from 2,4,6-trichloropyrido[2,3-d]pyrimidine 6 using 4-methoxyphenyl boronic acid (1.05 equiv), as a white solid in 83%yield.
  • 19
  • [ 52833-94-0 ]
  • [ 1234616-70-6 ]
  • 20
  • [ 1234616-70-6 ]
  • C25H19N3O2S [ No CAS ]
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