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[ CAS No. 41110-29-6 ] {[proInfo.proName]}

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Product Details of [ 41110-29-6 ]

CAS No. :41110-29-6 MDL No. :MFCD08705766
Formula : C7H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :AUDOINDPGADJPY-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :13153469
Synonyms :

Calculated chemistry of [ 41110-29-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.28
TPSA : 52.08 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 0.37
Log Po/w (WLOGP) : 0.57
Log Po/w (MLOGP) : -0.52
Log Po/w (SILICOS-IT) : 1.15
Consensus Log Po/w : 0.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.29
Solubility : 7.84 mg/ml ; 0.0515 mol/l
Class : Very soluble
Log S (Ali) : -1.03
Solubility : 14.2 mg/ml ; 0.0936 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.1
Solubility : 1.21 mg/ml ; 0.00796 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 41110-29-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 41110-29-6 ]

* 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.

  • Upstream synthesis route of [ 41110-29-6 ]
  • Downstream synthetic route of [ 41110-29-6 ]

[ 41110-29-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 41110-28-5 ]
  • [ 41110-29-6 ]
YieldReaction ConditionsOperation in experiment
73% at 80℃; for 5 h; In a 2-E flask, 3-methylpyrazine-2-carboxylic acid (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mE). The suspension was cooled in an ice-water bath, and concentrated sulfuric acid (Fluka, 27.3 mE, 506 mmol) was added over a time period of 5 mm. The reaction mixture was heated to 80° C. for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mE). The excess acid was neutralized careffilly with aqueous NaOH (SM, 200 mE). The aqueous layer was separated and extracted with DCM (250 mE). The combined organic layers were combined, dried over Mg504 and concentrated to afford the title compound (16.15 g, 106 mmol, 73percent). MS mlz=153 (M+H).
73% With sulfuric acid In methanol at 80℃; for 5 h; In a 2-L flask, 3-methylpyrazine-2-carboxylic acid (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mL). The suspension was cooled in an ice-water bath, and A-1813-WO-PCT - 148 - concentrated sulfuric acid (Fluka, 27.3 mL, 506 mmol) was added over a time period of 5 min. The reaction mixture was heated to 80 °C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mL). The excess acid was neutralized carefully with of aqueous NaOH (5N or 5M, 200 mL). The aqueous layer was separated and extracted with DCM (250 mL). The combined organic layers were combined, dried over MgS04 and concentrated to afford 16.15 g of the title compound (106 mmol, 73percent). MS m/z=153 [M+H]+. Calculated for C7H8N202: 152
73% at 80℃; for 5 h; Cooling with ice In a 2-L flask, 3-methylpyrazine-2-carboxylic acid (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mL). The suspension was cooled in an ice-water bath, and concentrated sulfuric acid (Fluka, 27.3 mL, 506 mmol) was added over a time period of 5 min. The reaction mixture was heated to 80 °C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mL). The excess acid was neutralized carefully with of aqueous NaOH (5 M, 200 mL). The aqueous layer was separated and extracted with DCM (250 mL). The combined organic layers were combined, dried over MgSO4 and concentrated to afford 16.15 g of methyl 3-methylpyrazine-2-carboxylate (265A, 106 mmol, 73percent). MS m/z=153 [M+H]+.
67% for 5 h; Reflux To a cooled suspension of 3-methylpyrazine-2-carboxylic acid (5.00 g, 36.2 mmol) in methanol (127 mL) was slowly added concentrated sulfuric acid (13.5 g, 7.34 mL, 127 mmol). The reaction mixture was heated to reflux for 5 h. After this time, LCMS analysis showed only a single peak, with a mass corresponding to the desired product. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in dichloromethane and washedwith excess aqueous 2N NaOH. The organic layer was kept and the aqueous re-extracted with a further 2 portions of dichloromethane. The combined organics were dried over MgSO4, filtered, and concentrated in vacuo to provide the desired ester (3.7 g, 67 percent) as a yellow solid. The product was used without further purification in subsequent reactions.1H-NMR (400 MHz, CDCI3): ö = 8.63 (d, J=2.3 Hz, 1H), 8.53 (d, J=2.0 Hz, 1H), 4.02 (s, 3H), 2.87 (s, 3H).

Reference: [1] Patent: US2014/213581, 2014, A1, . Location in patent: Paragraph 0773; 0793
[2] Patent: WO2014/138484, 2014, A1, . Location in patent: Page/Page column 147; 148
[3] Patent: WO2016/22724, 2016, A1, . Location in patent: Page/Page column 292; 293
[4] Patent: WO2016/174073, 2016, A1, . Location in patent: Page/Page column 44
[5] Patent: WO2010/130970, 2010, A1, . Location in patent: Page/Page column 39-40
[6] Patent: US2015/38497, 2015, A1, . Location in patent: Paragraph 0981; 0982
  • 2
  • [ 41110-28-5 ]
  • [ 41110-29-6 ]
Reference: [1] Patent: US2014/249104, 2014, A1, . Location in patent: Page/Page column
  • 3
  • [ 41110-29-6 ]
  • [ 1166831-45-3 ]
  • [ 1262860-62-7 ]
YieldReaction ConditionsOperation in experiment
1.5 g
Stage #1: With urea hydrogen peroxide adduct; trifluoroacetic anhydride In dichloromethane at 0 - 20℃; for 19 h;
Stage #2: With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide; toluene at 0 - 65℃; for 22 h; Inert atmosphere
A solution of mixture of 2-(methoxycarbonyl)-3-methylpyrazine 1-oxide compound with 3-(methoxycarbonyl)-2-methylpyrazine 1-oxide (1:1) (5.1 g, 15.17 mmol) in toluene (50 mL) was cooled to 0° C. To the mixture was added phosphorus oxychloride (2.78 ml, 30.3 mmol) under nitrogen followed by n,n′-dimethylformamide (0.117 ml, 1.517 mmol). The reaction mixture was stirred at room temperature for 4 h and then was heated to 65° C. for 18 h. The mixture was cooled to room temperature, diluted with EtOAc and washed with saturated NaHCO3 solution. The aqueous layer was back-extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The mixture was purified with ISCO (0percent to 50percent EtOAc/Hexanes) to afford both isomers: methyl 5-chloro-3-methylpyrazine-2-carboxylate (0.68 g, 48.1percent yield) and methyl 6-chloro-3-methylpyrazine-2-carboxylate (1.5 g, 106percent yield).
0.68 g
Stage #1: With urea hydrogen peroxide adduct; trifluoroacetic anhydride In dichloromethane at 0 - 20℃; for 19 h;
Stage #2: With trichlorophosphate In N,N-dimethyl-formamide; toluene at 0 - 65℃; for 22 h; Inert atmosphere
A solution of methyl 3-methylpyrazine-2-carboxylate (9.1 g, 59.8 mmol) in DCM (100 mL) was cooled to 0° C. was added urea hydrogen peroxide adduct (7.8 g, 83.0 mmol), followed by dropwise addition of trifluoroacetic acid anhydride (10.8 mL, 78.0 mmol). The resulting mixture was stirred at 0° C. for 1 h, and at RT for 18 h, during which LCMS indicated a mixture of two peaks corresponding to MS m/z=169.0 [M+H]+. The reaction was diluted with DCM and quenched with saturated Na2SO3 solution; the aqueous layer was back-extracted with DCM (2×). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. ISCO purification (20-80percent EtOAc/hexanes) afforded a mixture of two regioisomers, containing 3-(methoxycarbonyl)-2-methylpyrazine 1-oxide and 2-(methoxycarbonyl)-3-methylpyrazine 1-oxide (5.2 g, 30.9 mmol, 51.7percent yield). The mixture of regioisomers was taken to next step without further purification. MS m/z=169.0 [M+H]+. A solution of the mixture of 3-(methoxycarbonyl)-2-methylpyrazine 1-oxide and 2-(methoxycarbonyl)-3-methylpyrazine 1-oxide (5.1 g, 15.2 mmol) in toluene (50 mL) was cooled to 0° C. and phosphorus oxychloride (2.8 mL, 30.3 mmol) was added under nitrogen followed by DMF (0.12 mL, 1.52 mmol). The reaction mixture was stirred at RT for 4 h, and heated to 65° C. for 18 h, cooled to RT, diluted with EtOAc and washed with saturated NaHCO3 solution. The aqueous layer was back-extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. ISCO purification (0-50percent EtOAc/hexanes) with care afforded both isomers: methyl 5-chloro-3-methylpyrazine-2-carboxylate (0.68 g) (minor product) denoted by peak 1 and methyl 6-chloro-3-methylpyrazine-2-carboxylate (1.50 g) (major product) denoted by peak 2. MS m/z=187.0 [M+H]+. Peak 1: 1H NMR (300 MHz, DMSO-d6) δ 8.73 (s, 1H), 3.91 (s, 3H), 2.71 (s, 3H). Peak 2: 1H NMR (300 MHz, DMSO-d6) δ 8.89 (s, 1H), 3.91 (s, 3H), 2.71 (s, 3H).
0.68 g
Stage #1: With dihydrogen peroxide; trifluoroacetic anhydride In dichloromethane at 0 - 20℃; for 19 h;
Stage #2: With N,N-dimethyl-formamide; trichlorophosphate In toluene at 0 - 65℃; for 22 h;
A solution of methyl 3-methylpyrazine-2- carboxylate (265A, 9.1 g, 59.8 mmol) in DCM (100 mL) was cooled to 0 °C was added urea hydrogen peroxide adduct (7.8 g, 83.0 mmol), followed by dropwise addition of trifluoroacetic acid anhydride (10.8 mL, 78.0 mmol). The resulting mixture was stirred at 0 °C for 1 h, and at RT for 18 h, during which LCMS indicated a mixture of two peaks corresponding to MS m/z = 169.0 [M+H]+. The reaction was diluted with DCM and quenched with saturated Na2SO3 solution; the aqueous layer was back-extracted with DCM (2 x). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. ISCO purification (20-80percent EtOAc/hexanes) afforded a mixture of two regioisomers, containing 3-(methoxycarbonyl)-2-methylpyrazine 1 -oxide and 2- (methoxycarbonyl)-3-methylpyrazine 1 -oxide (5.2 g, 30.9 mmol, 51.7percent yield). The mixture of regioisomers was taken to next step without further purification. MS m/z = 169.0 [M+H]+. A solution of the mixture of 3-(methoxycarbonyl)-2-methylpyrazine 1 - oxide and 2-(methoxycarbonyl)-3-methylpyrazine 1 -oxide (5.1 g, 15.2 mmol) in toluene (50 mL) was cooled to 0 °C and phosphorus oxychloride (2.8 mL, 30.3 mmol) was added under nitrogen followed by DMF (0.12 mL, 1.52 mmol). The reaction mixture was stirred at RT for 4 h, and heated to 65 °C for 18 h, cooled to RT, diluted with EtOAc and washed with saturated NaHCO3 solution. The aqueous layer was back-extracted with EtOAc (2 x). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. ISCO purification (0-50percent EtOAc/hexanes) with care afforded both isomers: methyl 5-chloro-3-methylpyrazine-2-carboxylate (265B, 0.68 g) (minor product) denoted by peak 1 and methyl 6-chloro-3-methylpyrazine-2-carboxylate (265B1, 1.50 g) (major product) denoted by peak 2. MS m/z = 187.0 [M+H]+. Peak 1 : 1H NMR (300 MHz, DMSO-d6) δ 8.73 (s, 1 H), 3.91 (s, 3H), 2.71 (s, 3H). Peak 2: 1H NMR (300 MHz, DMSO-d6) δ 8.89 (s, 1 H), 3.91 (s, 3H), 2.71 (s, 3H).
Reference: [1] Patent: US2014/213581, 2014, A1, . Location in patent: Paragraph 0775
[2] Patent: US2015/38497, 2015, A1, . Location in patent: Paragraph 0978
[3] Patent: WO2016/22724, 2016, A1, . Location in patent: Page/Page column 300; 301
  • 4
  • [ 41110-29-6 ]
  • [ 1166831-45-3 ]
Reference: [1] Patent: US2012/172359, 2012, A1,
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