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CAS No. : | 1370411-44-1 | MDL No. : | MFCD19707615 |
Formula : | C15H13Cl2N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XLMNHZAOTDBGMV-UHFFFAOYSA-N |
M.W : | 338.19 | Pubchem ID : | 56965748 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 87.26 |
TPSA : | 55.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.96 cm/s |
Log Po/w (iLOGP) : | 3.36 |
Log Po/w (XLOGP3) : | 3.39 |
Log Po/w (WLOGP) : | 2.79 |
Log Po/w (MLOGP) : | 2.29 |
Log Po/w (SILICOS-IT) : | 3.31 |
Consensus Log Po/w : | 3.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.21 |
Solubility : | 0.0208 mg/ml ; 0.0000614 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.23 |
Solubility : | 0.0199 mg/ml ; 0.0000588 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.63 |
Solubility : | 0.000793 mg/ml ; 0.00000234 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.77 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate / 1,4-dioxane / 110 - 120 °C | ||
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate / 1,4-dioxane / 110 - 120 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate / 1,4-dioxane / 110 - 120 °C 3: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 3 h | ||
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate / 1,4-dioxane / 110 - 120 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water; ethanol / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate / 1,4-dioxane / 110 - 120 °C 3: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 3 h 4: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 0.5 h / 100 °C | ||
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate / 1,4-dioxane / 110 - 120 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water; ethanol / 3 h 4: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 0.5 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate / 1,4-dioxane / 110 - 120 °C 3: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 3 h 4: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 0.5 h / 100 °C 5: dichloromethane / 1 h / 20 °C | ||
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate / 1,4-dioxane / 110 - 120 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water; ethanol / 3 h 4: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 0.5 h / 100 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 20 °C / Cooling with ice 2: caesium carbonate / 1,4-dioxane / 120 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 20 °C / Cooling with ice 2: caesium carbonate / 1,4-dioxane / 120 °C / Sealed tube 3: hydrogen; palladium 10% on activated carbon / methanol / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 20 °C / Cooling with ice 2: caesium carbonate / 1,4-dioxane / 120 °C / Sealed tube 3: hydrogen; palladium 10% on activated carbon / methanol / 1 h 4: caesium carbonate; methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 70 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 20 °C / Cooling with ice 2.1: caesium carbonate / 1,4-dioxane / 120 °C / Sealed tube 3.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h 4.1: caesium carbonate; methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 70 °C / Sealed tube 5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.2: 0.02 h / -30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With N-ethyl-N,N-diisopropylamine at 20℃; | 191.A Step A: Benzyl 4-((3S,5R)-4-(tert-butoxycarbonyl)-3,5-dimethylpiperazin-1-yl)-2-chloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate: A suspension of benzyl 2,4-dichloro- 5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate (500 mg, 1.48 mmol), tert-butyl cis-2,6- dimethylpiperazine-l-carboxylate (349 mg, 1.63 mmol) and DIEA (0.26 mL) π Ν,Ν- dimethylacetamide (1 mL) was stirred at r.t. overnight. The reaction mixture was divided between EtOAc (15 mL) and 1M NaHCCb (5 mL) and the layers separated. The organic layer was washed with 2M Na2CCb and brine (2 mL each), dried over Na2S04 and evaporated in vacuo. The residue was chromatographed on silica gel Redisep 24g column using 20 to 50% EtOAc in hexane as eluent to give a colorless solid (0.440 g, 58%). ES+APCI MS m/z 516.2 [M+H]+. |
58% | With N-ethyl-N,N-diisopropylamine at 20℃; | 191.A Example 191 1-((2S,6R)-4-(7-(3-hydroxynaphthalen-1-yl)-2-(3-morpholinopropoxy)-5,6,7,8- -tetrahydropyrido [3,4-d]pyrimidin-4-yl)-2,6-dimethylpiperazin-1-yl)prop-2-en-1-one Step A: Benzyl 4-((3S,5R)-4-(tert-butoxycarbonyl)-3,5-dimethylpiperazin-1-yl)-2-chloro-5- ,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate A suspension of benzyl 2,4-dichloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate (500 mg, 1.48 mmol), tert-butyl cis-2,6-dimethylpiperazine-1-carboxylate (349 mg, 1.63 mmol) and DIEA (0.26 mL) in N,N-dimethylacetamide (1 mL) was stirred at r.t. overnight. The reaction mixture was divided between EtOAc (15 mL) and 1M NaHCO 3 (5 mL) and the layers separated. The organic layer was washed with 2M Na 2CO 3 and brine (2 mL each), dried over Na 2SO 4 and evaporated in vacuo. The residue was chromatographed on silica gel Redisep 24 g column using 20 to 50% EtOAc in hexane as eluent to give a colorless solid (0.440 g, 58%). ES+APCI MS m/z 516.2 [M+H] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; for 1h; Cooling with ice; | 256.A Step A: benzyl 4-(4-(tert-butoxycarbonyl)-3-(methoxymethyl)piperazin-1-yl)-2-chloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate: A solution of tert-butyl 2- (methoxymethyl)piperazine-l-carboxylate (0.715 g, 3.10 mmol) in N,N-dimethylacetamide (3 ml) was cooled on an ice bath with stirring and solid benzyl 2,4-dichloro-5,8-dihydropyrido[3,4- d]pyrimidine-7(6H)-carboxylate (1.00 g, 2.96 mmol) was added in small portions, followed by DIPEA (0.57 mL, 3.25 mmol, 1.1 eq.). The resulting solution was allowed to warm up to r.t. over 1 hour, and then divided between water (15 mL) and MTBE (50 mL). The organic layer was washed with water (2 x 10 mL), brine (10 mL), dried over Na2S04 and evaporated in vacuo to give a yellow solid (1.54 g, 98%). ES+APCI MS m/z 532.3, [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide | 5.A Step A. benzyl 4-((1R,5S)-8-(tert-butoxycarbonyl)-3,8-diazabicyclo[3.2.1]octan- 3-yl)-2-chloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate A solution of benzyl 2,4- dichloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate (2.0 g, 5.9 mmol) in DMA (10 mL) was added to a solution of 8-Boc-3,8-diazabicyclo[3.2.1]octane (1.3 g, 5.9 mmol) and DIEA (3.1 mL, 17 mmol) in DMA (5 mL). The reaction was stirred at room temperature overnight before being diluted with water and extracted with EtOAc. The organic layer was dried with Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 0-50% EtOAc/hexanes) to yield benzyl 4-((1R,5S)-8-(tert-butoxycarbonyl)-3,8- diazabicyclo[3.2.1]octan-3-yl)-2-chloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate as a white solid (1.4 g, 46%). LCMS (MM-ES+APCI, Pos): m/z 514.3 (M+H). |
In N,N-dimethyl-formamide Cooling; | 2.A Step A. benzyl 4-((1R,5S)-8-(tert-butoxycarbonyl)-3,8-diazabicyclo[3.2.1]octan- 3-yl)-2-chloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate To a suspension of tert- butyl (1R,5S)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (1.3 g , 6.2 mmol) and N-ethyl-N- isopropylpropan-2-amine (1.2 mL, 7.1 mmol) in N,N-dimethylacetamide (5 mL) was added benzyl 2,4-dichloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (2.0 g, 5.9 mmol) and the suspension was stirred on a cold water bath. The reaction mixture was partitioned between 0.5M NaHCO3 (30 mL) and DCM (50 mL). The organic layer was dried over Na2CO3 and evaporated in vacuo. The residue was dissolved in MTBE (20 mL), filtered, and evaporated in vacuo. The material was used crude in the next reaction. LCMS (MM-ES+APCI, Pos): m/z 514.3 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 19 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 19 h / 100 °C / Inert atmosphere 5: Cs2CO3; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / tetrahydrofuran / 6 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 15 h / 100 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 4.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 19 h / 100 °C / Inert atmosphere 5: Cs2CO3; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / tetrahydrofuran; toluene / 17 h / 90 °C / Inert atmosphere 6: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 15 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 15 h / 100 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 4.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 15 h / 100 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 4.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 19 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 15 h / 100 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 4.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 19 h / 100 °C / Inert atmosphere 5: Cs2CO3; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / tetrahydrofuran; toluene / 17 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 23 h / 105 °C / Inert atmosphere 5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / dichloromethane / 15 h / 90 °C / Inert atmosphere 6: dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 23 h / 105 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 23 h / 105 °C / Inert atmosphere 5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / dichloromethane / 15 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere 5: dichloromethane / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2.1: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 4 h / 100 °C / Inert atmosphere 3.1: hydrogen; palladium hydroxide on carbon, 20% / methanol; water monomer / 4.5 h / 20 °C 4.1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere 6.1: triethylamine / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 6.2: 1 h / 20 °C / Inert atmosphere 7.1: dichloromethane / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2.1: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 4 h / 100 °C / Inert atmosphere 3.1: hydrogen; palladium hydroxide on carbon, 20% / methanol; water monomer / 4.5 h / 20 °C 4.1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere 6.1: triethylamine / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 6.2: 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); sodium tertiary butoxide / toluene / 2 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 6 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 7.5 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / 1,4-dioxane / 95 °C / Inert atmosphere; Sealed tube 3: hydrogen; palladium on activated charcoal / methanol / 1 h 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube 5: boron tribromide / dichloromethane / 1.75 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / 1,4-dioxane / 95 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / 1,4-dioxane / 95 °C / Inert atmosphere; Sealed tube 3: hydrogen; palladium on activated charcoal / methanol / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / 1,4-dioxane / 95 °C / Inert atmosphere; Sealed tube 3: hydrogen; palladium on activated charcoal / methanol / 1 h 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2.1: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 4 h / 100 °C / Inert atmosphere 3.1: hydrogen; palladium hydroxide on carbon, 20% / methanol; water monomer / 4.5 h / 20 °C 4.1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere 6.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.2: 1 h / 20 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 4 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 4 h / 100 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol; water monomer / 4.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 4 h / 100 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol; water monomer / 4.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 4 h / 100 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol; water monomer / 4.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2.1: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 4 h / 100 °C / Inert atmosphere 3.1: hydrogen; palladium hydroxide on carbon, 20% / methanol; water monomer / 4.5 h / 20 °C 4.1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere 6.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.2: 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide 2: Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 110 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon, 20% / methanol / 7.5 h / 20 °C 4: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 19 h / 100 °C / Inert atmosphere 5: Cs2CO3; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / tetrahydrofuran / 6 h / 90 °C / Inert atmosphere 6: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -20 - 20℃; for 24h; | |
63.6 % | With triethylamine In tetrahydrofuran at 25℃; | 1.1 Step 1: Benzyl 4-(8-tert-butoxycarbonyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-2-chloro-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-7-carboxylate To a solution of benzyl 2, 4-dich loro-6, 8-di hydro-5 H-pyrido[ 3, 4-dJpyri midinc-7-carboxylate (1 g, 2.96 mmol, 1 eq) and tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (564.95 mg, 2.66 mmol, 0.9 eq) in THF (10 mL) was added TEA (897.63 mg, 8.87 mmol, 1.23 mL, 3 eq). The mixture was stirred at 25 °C for 12 h. The reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (20 mL x 3). The combined organics were concentrated to yield the crude product which was purified by flash silica gel chromatography (from PE/EtOAc = 100/1 to 3/1, TLC: PE/EtOAc = 3/1, Rf = 0.42) to yeild benzyl 4-(8-tert-butoxycarbonyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-2-chloro-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-7-carboxylate (1 g, 1.88 mmol, 63.6% yield, 96.6% purity) as a gray solid.1H NMR (400 MHz, DMSO-d6) d ppm 7.41-7.32 (m, 5H), 5.13 (s, 2H), 4.44 (d, J = 19.6 Hz, 2H), 4.16 (s, 2H), 3.90 (d, J = 12.3 Hz, 2H), 3.53 (s, 2H), 3.11 (d, J= 12.4 Hz, 2H), 2.68 (s, 2H), 1.78 (d, J = 4.4 Hz, 2H), 1.69 (d, J = 8.0 Hz, 2H), 1.42 (s, 9H); ES-LCMS m/z 514.7, 516.7 [M+H]+. |
63.6 % | With triethylamine In tetrahydrofuran at 25℃; | 1.1 Step 1: Benzyl 4-(8-tert-butoxycarbonyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-2-chloro-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-7-carboxylate To a solution of benzyl 2, 4-dich loro-6, 8-di hydro-5 H-pyrido[ 3, 4-dJpyri midinc-7-carboxylate (1 g, 2.96 mmol, 1 eq) and tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (564.95 mg, 2.66 mmol, 0.9 eq) in THF (10 mL) was added TEA (897.63 mg, 8.87 mmol, 1.23 mL, 3 eq). The mixture was stirred at 25 °C for 12 h. The reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (20 mL x 3). The combined organics were concentrated to yield the crude product which was purified by flash silica gel chromatography (from PE/EtOAc = 100/1 to 3/1, TLC: PE/EtOAc = 3/1, Rf = 0.42) to yeild benzyl 4-(8-tert-butoxycarbonyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-2-chloro-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-7-carboxylate (1 g, 1.88 mmol, 63.6% yield, 96.6% purity) as a gray solid.1H NMR (400 MHz, DMSO-d6) d ppm 7.41-7.32 (m, 5H), 5.13 (s, 2H), 4.44 (d, J = 19.6 Hz, 2H), 4.16 (s, 2H), 3.90 (d, J = 12.3 Hz, 2H), 3.53 (s, 2H), 3.11 (d, J= 12.4 Hz, 2H), 2.68 (s, 2H), 1.78 (d, J = 4.4 Hz, 2H), 1.69 (d, J = 8.0 Hz, 2H), 1.42 (s, 9H); ES-LCMS m/z 514.7, 516.7 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / -20 - 20 °C 2: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / -20 - 20 °C 2: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C 3: palladium 10% on activated carbon / methanol / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / -20 - 20 °C 2: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C 3: palladium 10% on activated carbon / methanol / 15 h / 20 °C 4: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / -20 - 20 °C 2: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C 3: palladium 10% on activated carbon / methanol / 15 h / 20 °C 4: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C 5: trifluoroacetic acid / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / -20 - 20 °C 2: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C 3: palladium 10% on activated carbon / methanol / 15 h / 20 °C 4: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate / toluene / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / -20 - 20 °C 2: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C 3: palladium 10% on activated carbon / methanol / 15 h / 20 °C 4: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate / toluene / 100 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / -20 - 20 °C 2: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C 3: palladium 10% on activated carbon / methanol / 15 h / 20 °C 4: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 16 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / -20 - 20 °C 2: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine / toluene / 85 °C 3: palladium 10% on activated carbon / methanol / 15 h / 20 °C 4: tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 16 h / 100 °C 5: trifluoroacetic acid / dichloromethane / 16 h / 20 °C |
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