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CAS No. : | 337958-60-8 | MDL No. : | MFCD11518965 |
Formula : | C8H4Cl2N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HNRPBMNTCYRAJD-UHFFFAOYSA-N |
M.W : | 199.04 | Pubchem ID : | 12204233 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 49.56 |
TPSA : | 25.78 Ų |
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) : | -5.36 cm/s |
Log Po/w (iLOGP) : | 1.95 |
Log Po/w (XLOGP3) : | 3.04 |
Log Po/w (WLOGP) : | 2.94 |
Log Po/w (MLOGP) : | 2.03 |
Log Po/w (SILICOS-IT) : | 3.21 |
Consensus Log Po/w : | 2.63 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.0493 mg/ml ; 0.000248 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.25 |
Solubility : | 0.113 mg/ml ; 0.000566 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.57 |
Solubility : | 0.00542 mg/ml ; 0.0000272 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
0.42 g | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70 - -60℃; for 1.5 h; Inert atmosphere Stage #2: at -70 - 20℃; for 0.833333 h; Inert atmosphere |
Intermediate 7: 5,7-Dichloro-1,6-naphthyridine[0384]N-(2,6-Dichloro-4-pyridinyl)-2,2-dimethylpropanamide (1 g, 4.05 mmol) was taken up in THF (10 ml) under nitrogen and cooled to n-Butyl lithium (4.05 ml, 10.12 mmol, 2.5M solution in hexanes) was added over 30 min keeping the temperature below −60° C. and then stirred at below −70° C. for 1 h. (2E)-3-(dimethylamino)-2-propenal (0.607 ml, 6.07 mmol) in THF (2 ml) was added over 30 min keeping the temperature below −60° C. The reaction was stirred at below −70° C. for 20 min and then allowed to warm to room temperature. LCMS showed that no starting material remained so the reaction was quenched with 5M HCl (5 ml) and refluxed overnight. LCMS showed good conversion to product so the reaction was cooled to room temperature. The reaction mixture was basified with solid K2CO3 and extracted with EtOAc (4×25 ml). The combined organics were dried with Na2SO4, filtered and concentrated to yield a brown solid. The crude product was applied to a samplet and columned using a 40+M eluting with 12percent diethyl ether in cyclohexane for 2 CVs, then with 12percent-63percent diethyl ether in cyclohexane over 10 CVs then held at 63percent for SCVs. Appropriate fractions were combined and evaporated to give the title compound as a yellow solid (0.42 g).[0386]LCMS (Method B): Rt=0.89 min, MH+ 199/201 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
/V-(2,6-Dichloro-4-pyridinyl)-2,2-dimethylpropanamide (1 g, 4.05mmol) was taken up in THF (10ml) under nitrogen and cooled to <-70C. n-Butyl lithium (4.05ml, 10.12mmol, 2.5M solution in hexanes) was added over 30min keeping the temperature below -60C and then stirred at below -70C for 1 h. (2£)-3- (dimethylamino)-2-propenal (0.607ml, 6.07mmol) in THF (2ml) was added over 30min keeping the temperature below -60C. The reaction was stirred at below -70C for 20min and then allowed to warm to room temperature. LCMS showed that no starting material remained so the reaction was quenched with 5M HCI (5ml) and refluxed overnight. LCMS showed good conversion to product so the reaction was cooled to room temperature. The reaction mixture was basified with solid K2C03 and extracted with EtOAc (4x25ml). The combined organics were dried with Na2S04, filtered and concentrated to yield a brown solid. The crude product was applied to a samplet and columned using a 40+M eluting with 12% diethyl ether in cyclohexane for 2CVs, then with 12%-63% diethyl ether in cyclohexane over 10CVs then held at 63% for 5CVs. Appropriate fractions were combined and evaporated to give the title compound as a yellow solid (0.42g).LCMS (Method B): Rt = 0.89min, MH+ 199/201 | ||
0.42 g | Intermediate 7: 5,7-Dichloro-1,6-naphthyridine[0384]N-(2,6-Dichloro-4-pyridinyl)-2,2-dimethylpropanamide (1 g, 4.05 mmol) was taken up in THF (10 ml) under nitrogen and cooled to n-Butyl lithium (4.05 ml, 10.12 mmol, 2.5M solution in hexanes) was added over 30 min keeping the temperature below -60 C. and then stirred at below -70 C. for 1 h. (2E)-3-(dimethylamino)-2-propenal (0.607 ml, 6.07 mmol) in THF (2 ml) was added over 30 min keeping the temperature below -60 C. The reaction was stirred at below -70 C. for 20 min and then allowed to warm to room temperature. LCMS showed that no starting material remained so the reaction was quenched with 5M HCl (5 ml) and refluxed overnight. LCMS showed good conversion to product so the reaction was cooled to room temperature. The reaction mixture was basified with solid K2CO3 and extracted with EtOAc (4×25 ml). The combined organics were dried with Na2SO4, filtered and concentrated to yield a brown solid. The crude product was applied to a samplet and columned using a 40+M eluting with 12% diethyl ether in cyclohexane for 2 CVs, then with 12%-63% diethyl ether in cyclohexane over 10 CVs then held at 63% for SCVs. Appropriate fractions were combined and evaporated to give the title compound as a yellow solid (0.42 g).[0386]LCMS (Method B): Rt=0.89 min, MH+ 199/201 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 72h;Inert atmosphere;Product distribution / selectivity; | To 5,7-dichloro-1 ,6-naphthyridine (5.01 g, 25.2mmol) and 1 , 1 -dimethylethyl (3R)-3- (aminomethyl)-3-fluoro-1 -piperidinecarboxylate (5.32g, 22.90mmol) in NMP (20ml) was added DI PEA (8.00ml, 45.8mmol) and the mixture was stirred at 100C for 72h under nitrogen. The reaction was cooled and partitioned between ethyl acetate and water (200ml each). The aqueous was washed with ethyl acetate. The combined organics were washed with water and the solvent was removed. The residue was dissolved in DCM and loaded onto a 100g silica SNAP column and purified on the SP4 eluting with 0-50% ethyl acetate in cyclohexane over 17CVs. Appropriate fractions were combined and the solvent was removed to give the title compound as a pale orange solid which was dried under high vacuum for 2h (7.61 g).LCMS (Method B): Rt = 1 .12min, MH+ 395/397 | |
7.61 g | With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 72h;Inert atmosphere; | Intermediate 8: 1,1-Dimethylethyl (3R)-3-[(7-chloro-1,6-naphthyridin-5-yl)amino]methyl}-3-fluoro-1-piperidinecarboxylate[0387]<strong>[337958-60-8]5,7-dichloro-1,6-naphthyridine</strong> (5.01 g, 25.2 mmol) and 1,1-dimethylethyl (3R)-3-(aminomethyl)-3-fluoro-1-piperidinecarboxylate (5.32 g, 22.90 mmol) in NMP (20 ml) was added DIPEA (8.00 ml, 45.8 mmol) and the mixture was stirred at 100 C. for 72 h under nitrogen. The reaction was cooled and partitioned between ethyl acetate and water (200 ml each). The aqueous was washed with ethyl acetate. The combined organics were washed with water and the solvent was removed. The residue was dissolved in DCM and loaded onto a 100 g silica SNAP column and purified on the SP4 eluting with 0-50% ethyl acetate in cyclohexane over 17 CVs. Appropriate fractions were combined and the solvent was removed to give the title compound as a pale orange solid which was dried under high vacuum for 2 h (7.61 g).[0389]LCMS (Method B): Rt=1.12 min, MH+ 395/397 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To an ice cooled solution of 1 ,1-dimethylethyl (3S)-3-fluoro-3-(hydroxymethyl)-1 - piperidinecarboxylate (1.406g, 6.03mmol) in DMF (20ml) was added sodium hydride (0.313g, 7.84mmol) (60% dispersion in mineral oil). This was stirred for 15min before adding 5,7-dichloro-1 ,6-naphthyridine (1 .2g, 6.03mmol). This was warmed to room temp and stirred for 4h. The reaction had gone to completion and so was cautiously quenched with aqueous ammonium chloride before partitioning between aqueous ammonium chloride and ethyl acetate. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine and concentrated in vacuo to give the crude product. This was dissolved in DCM and purified through silica (50g), eluting with a gradient of 0-50% ethyl acetate in DCM. Appropriate fractions were concentrated in vacuo to yield the title compound as a cream foamy gum (1.91 g).LCMS: Rt = 1.18min, MH+ = 395.85 | ||
1.91 g | Intermediate 16: 1,1-Dimethylethyl (3S)-3-[(7-chloro-1,6-naphthyridin-5-yl)oxy]methyl}-3-fluoro-1-piperidinecarboxylate[0413]1,1-dimethylethyl (3S)-3-fluoro-3-(hydroxymethyl)-1-piperidinecarboxylate (1.406 g, 6.03 mmol) in DMF (20 ml) was added sodium hydride (0.313 g, 7.84 mmol) (60% dispersion in mineral oil). This was stirred for 15 min before adding <strong>[337958-60-8]5,7-dichloro-1,6-naphthyridine</strong> (1.2 g, 6.03 mmol). This was warmed to room temp and stirred for 4 h. The reaction had gone to completion and so was cautiously quenched with aqueous ammonium chloride before partitioning between aqueous ammonium chloride and ethyl acetate. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine and concentrated in vacuo to give the crude product. This was dissolved in DCM and purified through silica (50 g), eluting with a gradient of 0-50% ethyl acetate in DCM. Appropriate fractions were concentrated in vacuo to yield the title compound as a cream foamy gum (1.91 g).[0415]LCMS: Rt=1.18 min, MH+=395.85 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetramethlyammonium chloride; trichlorophosphate; at 30 - 103.5℃; for 36h; | Phosphorus oxychloride (3vol) is charged to the reactor at 30+/-5C followed by 1 ,6- naphthyridin-5,7(6H,8H)-dione (1 eq), tetramethylammonium chloride (1.05eq) and a rinse of phosphorus oxychloride (0.5vol). The mixture is heated to 103.5+/-3.5C and stirred for a minimum of 36h. The reaction is then cooled to 60+/-5C and sampled. On receipt of a successful sample, toluene (4vol) is added and the mixture concentrated to 2-3 volumes by distillation under vacuum (NLT 650 mm of Hg) and temperature <60C. Additional toluene (2vol) is added and again the mixture distilled under vacuum to 2-3 vols. This toluene addition/distillation cycle is repeated once more then the mixture is cooled to 47.5+/-2.5C and treated with tetrahydrofuran (8vol) and ethyl acetate (8vol). The mixture is cooled to 30+/-5 C and poured into 15% aq. sodium carbonate (15vol) which has been pre-cooled to 5.0+/-5.0C. Additional tetrahydrofuran (3vol) is added along with ethyl acetate (3vol) in order to rinse out the initial reaction vessel. Whilst still at 5+/-5C the mixture is slowly treated with further 15% aqueous sodium carbonate solution (5vol) and stirred for 15-30min. The temperature is increased to 22.5+/-2.5C and the pH adjusted to 7-8 by addition of either 15% aqueous sodium carbonate solution or dilute HCI. Ethyl acetate (5vol) is added followed by celite. The mixture is stirred then filtered. The celite bed is washed with ethyl acetate (2x2vol). The filtrate is distilled at <55C under vacuum (NLT 650 mm of Hg) down to 30+/-5 volumes. Water (2vol) is added and the distilled again down to ~30vols. This water addition/distillation cycle is repeated until the tetrahydrofuran, toluene and ethyl acetate content are each NMT 3.0% by GC (% w/w). At that point, water (10vol) is added and the mixture heated to 42.5+/-2.5C and stirred for 30- 60min. The product is isolated by filtration at 42.5+/-2.5C and washed with water (2x3vol). The cake is sucked dry then offloaded and charged to a separate reactor. Water (20vol) is added and the suspension heated to 42.5+/-2.5C and stirred for 30- 60min 42.5+/-2.5C. The product is filtered and washed with water (2x3vol), sucked dry then transferred to a vacuum oven and further dried at 52.5+/- 2.5C under vacuum (NLT 650 mm of Hg) for 8+/-2h. | |
With tetramethlyammonium chloride; trichlorophosphate; at 103.5℃; for 36h; | Phosphorus oxychloride (3 vol) is charged to the reactor at 30±5 C. followed by 1,6-naphthyridin-5,7(6H,8H)-dione (1 eq), tetramethylammonium chloride (1.05 eq) and a rinse of phosphorus oxychloride (0.5 vol). The mixture is heated to 103.5±3.5 C. and stirred for a minimum of 36 h. The reaction is then cooled to 60±5 C. and sampled. On receipt of a successful sample, toluene (4 vol) is added and the mixture concentrated to 2-3 volumes by distillation under vacuum (NLT 650 mm of Hg) and temperature<60 C. Additional toluene (2 vol) is added and again the mixture distilled under vacuum to 2-3 vols. This toluene addition/distillation cycle is repeated once more then the mixture is cooled to 47.5±2.5 C. and treated with tetrahydrofuran (8 vol) and ethyl acetate (8 vol). The mixture is cooled to 30±5 C. and poured into 15% aq. sodium carbonate (15 vol) which has been pre-cooled to 5.0±5.0 C. Additional tetrahydrofuran (3 vol) is added along with ethyl acetate (3 vol) in order to rinse out the initial reaction vessel. Whilst still at 5±5 C. the mixture is slowly treated with further 15% aqueous sodium carbonate solution (5 vol) and stirred for 15-30 min. The temperature is increased to 22.5±2.5 C. and the pH adjusted to 7-8 by addition of either 15% aqueous sodium carbonate solution or dilute HCl. Ethyl acetate (5 vol) is added followed by celite. The mixture is stirred then filtered. The celite bed is washed with ethyl acetate (2×2 vol). The filtrate is distilled at <55 C. under vacuum (NLT 650 mm of Hg) down to 30±5 volumes. Water (2 vol) is added and the distilled again down to ?30 vols. This water addition/distillation cycle is repeated until the tetrahydrofuran, toluene and ethyl acetate content are each NMT 3.0% by GC (% w/w). At that point, water (10 vol) is added and the mixture heated to 42.5±2.5 C. and stirred for 30-60 min. The product is isolated by filtration at 42.5±2.5 C. and washed with water (2×3 vol). The cake is sucked dry then offloaded and charged to a separate reactor. Water (20 vol) is added and the suspension heated to 42.5±2.5 C. and stirred for 30-60 min 42.5±2.5 C. The product is filtered and washed with water (2×3 vol), sucked dry then transferred to a vacuum oven and further dried at 52.5±2.5 C. under vacuum (NLT 650 mm of Hg) for 8±2 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 110℃; for 16h; | To a 40 mL vial was added <strong>[337958-60-8]5,7-dichloro-1,6-naphthyridine</strong>, (510 mg, 2.56 mmol), tert-butyl (1R,3s,5S)-3 -amino-9-azabicyclo [3.3.1 jnonane-9-carboxylate (677 mg, 2.82 mmol), DIPEA (1.34 mL, 7.69 mmol), and DMSO (8.54 mL). The vial was capped and the reaction mixture was heated to 110 C and stirred for 16 h. The reaction mixture was5 diluted with water and brine and extracted with EtOAc (4 x 30 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to afford the desired product as a brown solid which was dissolved in a minimal amount of DCM and adsorbed onto Celite, purified by column chromatography (40 g column; 0-100% EtOAc in hexanes) to afford the title product as a yellow solid (901.6 mg, 86 % yield; 9910 % purity). (m/z): [M+Hj calcd for C21H27C1N402 403.18, found 403.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With N-iodo-succinimide; acetic acid; for 12h;Reflux; | A mixture of <strong>[337958-60-8]5,7-dichloro-1,6-naphthyridine</strong> (4.0 g, 20 mmol) and Niodosuccinimide (9.0 g, 37 mmol) in acetic acid (100 mL) was heated at reflux for 12 h. The reaction mixture was concentrated under vacuum, and the residue was purified by column chromatography 20:1 petroleum ether:EtOAc to provide the title intermediate as ayellow solid (2.4 g, 37 % yield). |
Tags: 337958-60-8 synthesis path| 337958-60-8 SDS| 337958-60-8 COA| 337958-60-8 purity| 337958-60-8 application| 337958-60-8 NMR| 337958-60-8 COA| 337958-60-8 structure
[ 952138-13-5 ]
4,7-Dichloro-1,6-naphthyridine
Similarity: 0.78
[ 952138-13-5 ]
4,7-Dichloro-1,6-naphthyridine
Similarity: 0.78
[ 931100-02-6 ]
4,6,8-Trichloro-1,7-naphthyridine
Similarity: 0.74
[ 107484-69-5 ]
5-Chloro-8-iodo-1,6-naphthyridine
Similarity: 0.70
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H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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