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[ CAS No. 25808-30-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 25808-30-4
Chemical Structure| 25808-30-4
Structure of 25808-30-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 25808-30-4 ]

CAS No. :25808-30-4 MDL No. :MFCD00012587
Formula : C3H7ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :DFKBQHBEROHUNF-UHFFFAOYSA-N
M.W : 106.55 Pubchem ID :117641
Synonyms :

Calculated chemistry of [ 25808-30-4 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 26.05
TPSA : 35.82 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) : -6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.38
Log Po/w (WLOGP) : 0.53
Log Po/w (MLOGP) : -0.33
Log Po/w (SILICOS-IT) : -0.42
Consensus Log Po/w : 0.03

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.67
Solubility : 22.6 mg/ml ; 0.212 mol/l
Class : Very soluble
Log S (Ali) : -0.7
Solubility : 21.4 mg/ml ; 0.201 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.67
Solubility : 23.0 mg/ml ; 0.216 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 25808-30-4 ]

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

Application In Synthesis of [ 25808-30-4 ]

* 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 [ 25808-30-4 ]
  • Downstream synthetic route of [ 25808-30-4 ]

[ 25808-30-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 24424-99-5 ]
  • [ 25808-30-4 ]
  • [ 121492-06-6 ]
Reference: [1] Patent: US6369034, 2002, B1,
  • 2
  • [ 79-37-8 ]
  • [ 25808-30-4 ]
  • [ 87486-33-7 ]
YieldReaction ConditionsOperation in experiment
70% at 90℃; bl . l) Compound (2) To a solution of cyano-N-methylmethanaminium chloride (6.4 g, 39.9 mmol) in chlorobenzene (50 ml) was added dropwise oxalyl chloride (12 ml, 137 mmol) at r. t., then the resulting solution was heated slowly to 90 °C and stirred overnight. The solvent was removed, the residue was purified by column chromatography on silica gel (PE:EA=10: 1) to give the title compound as yellow oil (5 g, 70percent yield). LC-MS (ESI+): m/e 178 (M+H)+, Rt: 1.54 min.
60% at 80℃; for 8 h; d) 3,5-Dichloro-1-methyl-1H-pyrazin-2-one (4c)[0245][0246]3.29 g (30.8 mmoles) of methylamino-acetonitrile hydrochloride is placed in the presence of 19.6 g (154 mmoles) of oxalyl chloride in 30 ml of 1,2-dichlorobenzene. The mixture is heated for 8 hours at 80° C. After concentrating the reaction medium to dryness, the residue obtained is purified by flash chromatography (Petroleum ether-CH2Cl2 gradient 100-0 to 0-100). 3.35 g of intermediate 4c is obtained in beige powder form (yield: 60percent).[0247]TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH: 90-10, Rf=0.79.
Reference: [1] Patent: WO2014/140184, 2014, A1, . Location in patent: Page/Page column 75
[2] Patent: US2013/40928, 2013, A1, . Location in patent: Paragraph 0245; 0246; 0247
[3] Journal of Heterocyclic Chemistry, 1983, vol. 20, # 4, p. 919 - 923
[4] Patent: US2010/298334, 2010, A1, . Location in patent: Page/Page column 56
  • 3
  • [ 15219-34-8 ]
  • [ 25808-30-4 ]
  • [ 87486-34-8 ]
YieldReaction ConditionsOperation in experiment
92% at 0 - 55℃; for 16 h; To a suspension of methylamino acetonitrile hydrochloride (20 g, 142.0 mmol) in DCM (1300 ml), was added oxalyl bromide (54 ml, 188.67 mmol) followed by slow addition of DMF (1.5 ml) at 0°C. The reaction mixture was stirred at 55°C for 16 h. DCM was concentrated under reduced pressure, the residue obtained was purified by column chromatography by eluting with 2percent MeOH/CH2Cl2 to afford the desired compound as a pale yellow solid (34 g, 92 percent); *H NMR (400MHz, DMSO-dg) δ 8.1 (s, 1H), 3.4 (s, 3H). LC-MS: 268.9 (M+l)+.
92% at 0 - 55℃; for 16 h; To a suspension of methylamino acetonitrile hydrochloride (20 g, 142.0 mmol) in DCM (1300 mL), was added oxalyl bromide (54 mL, 188.67 mmol) followed by slow addition of DMF (1.5 mL) at 0°C. The reaction mixture was stirred at 55°C for 16 h. DCM was concentrated underreduced pressure, the residue obtained was purified by colunm chromatography by eluting with2percent MeOH/CH2C12 to afford the desired compound as a pale yellow solid (34 g, 92percent); 1H NMR(400 MHz, DMSO-d6) ö 8.1 (s, 1H), 3.4 (s, 3H). LC-MS: 268.9 (M+1).
Reference: [1] Patent: WO2014/108820, 2014, A1, . Location in patent: Page/Page column 27
[2] Patent: WO2014/125410, 2014, A1, . Location in patent: Page/Page column 23; 24
  • 4
  • [ 15219-34-8 ]
  • [ 25808-30-4 ]
  • [ 68-12-2 ]
  • [ 87486-34-8 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: for 18 h; Reflux
Stage #2: for 18 h; Reflux
A 5-L three-neck RBF equipped with a mechanical stirrer, thermoregulator, reflux condenser andnitrogen inlet was charged with compound 5(181.0 g, 1.66 mol) and anhydrous DCM (1.5 L). Oxalyl bromide (367 g, 1.70 mol) wasadded and the stirring suspension was heated to reflux for 18 h (Caution: poisonous gas evolution). The reaction mixture was then cooled to 0 °C in an ice/water bath before anhydrous DMF (186 g, 2.55 mol) was slowly added (Caution: reaction was exothermic andfoaming with poisonous gas evolution). Dueto the exothermic nature of the reaction, mixture temperature rose to 12°C. Additional oxalyl bromide (550 g,2.55 mol) was added portion-wise (Caution: reaction was exothermic withpoisonous gas evolution). The mixturetemperature rose further to 16 °C. Afterthe addition, the reaction mixture was stirred in a cooling bath for 20 min andat 25 °C for 30 min and was heated to reflux for 18 h. Upon cooling to 25 °C, the reaction mixturewas poured into a 2.5 gal. carboy containing saturated aqueous sodiumbicarbonate (2 L) (Caution:foaming). Sodium bicarbonate (~405 g)was added portion-wise to adjust thepH to 8 (Caution: foaming). After separation, the aqueous layer wasextracted with DCM (3 × 1 L). Thecombined organic layers were dried over sodium sulfate, filtered andconcentrated under vacuum. The resultingresidue suspended in DCM (approximately 250 mL) was purified on a silica gelplug (glass frit, 6” diameter, 2.5” height of silica) and eluted with methylenechloride (approximately 5 L total). After evaporation, the desired product VI (317.2 g, 71percent) was obtained as a light reddish-brown solid (mp: 94–95 C);
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 6, p. 1333 - 1337
  • 5
  • [ 24424-99-5 ]
  • [ 25808-30-4 ]
  • [ 180976-09-4 ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine In dichloromethane at 20℃; for 168 h; To a suspension of methylaminoacetonitrile hydrochloride (11.45 g, 107.4 mmol) in DCM (100 ml_) was added triethylamine (31.5 mL, 226 mmol), followed by di-tert-butyl dicarbonate (22.3 g, 102.2 mmol) and the reaction mixture was stirred at room temperature over the weekend. The reaction mixture was filtered, concentrated in vacuo and purified over silica using a gradient of 10-20percent ethyl acetate/cyclohexane. The pure fractions were combined and concentrated to afford the title compound (11.94 g, 69percent) as a colourless liquid. LC-MS (Method 5): 2.82 min, [M+H]+ 171.1.
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 16, p. 3070 - 3088
[2] Patent: WO2008/23157, 2008, A1, . Location in patent: Page/Page column 115
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