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[ CAS No. 85333-43-3 ] {[proInfo.proName]}

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Chemical Structure| 85333-43-3
Chemical Structure| 85333-43-3
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Product Details of [ 85333-43-3 ]

CAS No. :85333-43-3 MDL No. :MFCD09999202
Formula : C7H6ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZZPUXAQVYFAAMQ-UHFFFAOYSA-N
M.W : 167.60 Pubchem ID :13389082
Synonyms :

Calculated chemistry of [ 85333-43-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.96
TPSA : 30.19 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) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 2.05
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 0.44
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.281 mg/ml ; 0.00167 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 0.816 mg/ml ; 0.00487 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.328 mg/ml ; 0.00195 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 85333-43-3 ]

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 [ 85333-43-3 ]

* 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 [ 85333-43-3 ]
  • Downstream synthetic route of [ 85333-43-3 ]

[ 85333-43-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 6863-73-6 ]
  • [ 78-95-5 ]
  • [ 85333-43-3 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: at 90℃; for 16 h; sealed tube protected from light
Stage #2: With sodium carbonate In water
A mixture of 3-chloro-pyrazin-2-ylamine (48.7 g, 375.8 mmol) and chloroacetone (120 ml, 1504.5 mmol) was stirred at 90 °C for 16 h. in a sealed tube protected from light. After cooling to RT, Et20 was added and the solid formed was filtered off, washed with further Et20, suspended in a saturated solution of sodium carbonate and extracted with DCM. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was precipitated from Et20 to yieldintermediate 4 (43.2 g, 68percent) as a white solid which was used in the next step without further purification. m.p. 133.5-138.6 °C (WRS-2A).
68%
Stage #1: at 90℃; for 16 h; Sealed tube; Darkness
Stage #2: With sodium carbonate In water
Example A4
8-Chloro-2-methyl-imidazol[1,2-a]pyrazine
A mixture of 3-chloro-pyrazin-2-ylamine (48.7 g, 375.8 mmol) and chloroacetone (120 ml, 1504.5 mmol) was stirred at 90° C. for 16 h. in a sealed tube protected from light.
After cooling to RT, Et2O was added and the solid formed was filtered off, washed with further Et2O, suspended in a saturated solution of sodium carbonate and extracted with DCM.
The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo.
The crude product was precipitated from Et2O to yield intermediate 4 (43.2 g, 68percent) as a white solid which was used in the next step without further purification. m.p. 133.5-138.6° C. (WRS-2A).
68% at 90℃; for 16 h; Sealed tube; Darkness A mixture of 3-chloro-pyrazin-2-ylamine (48.7 g, 375 8 mmol) and chloroacetone (120 ml, 1504.5 mmol) was stirred at 90 ° C. for 16 h. in a sealed tube protected from light. After cooling to RT, Et2O was added and the solid formed was filtered off, washed with further Et2O, suspended in a saturated solution of sodium carbonate and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was precipitated from Et2O to yield intermediate 6 (43.2 g, 68percent) as a white solid which was used in the next step without further purification. m.p. 133.5-138.6° C. (WRS-2A).
53% at 90℃; for 16 h; Sealed tube A mixture of 3-chloropyrazin-2-amine (2 g, 15.4 mmol) and 1-chloropropan-2-one (4mL) was heated to 90 °C for 16 h in a sealed tube. The reaction mixture was then cooled to roomtemperature and the solid formed was filtered, washed with ether and dried to get the titled compound (1.4 g, 53percent). LC-MS: 168.3 [M+Hj.
7.7% at 88℃; Heating / reflux A solution of 2-amino-3-chloropyrazine (1Og, 77.5mmol), chloroacetone (3OmL, 387mmol) in MeOH (25ml_) is refluxed overnight at 88°C. It is then stirred for Ih at O0C and any solid that forms, is filtered off and washed twice with MeOH (5ml_). The mother liq. are evaporated, diluted with EtOAc, and washed with HCI 2N, water and brine. The water and HCI mother liq. are evaporated to give a yellow solid that is neutralized with a saturated solution of K2CO3 in water, extracted with DCM, dried with MgSO4 anh. filtered and concentrated. The crude material is purified by column chromatography using a gradient of (DCM/MeOH: 1/0 to 99/1) to give 8-Chloro-2-methyl-imidazo[l,2-a]pyrazine as an orange solid (1.02g, 7.7percent).

Reference: [1] Patent: WO2011/110545, 2011, A1, . Location in patent: Page/Page column 73-74
[2] Patent: US2012/329792, 2012, A1, . Location in patent: Page/Page column 33-34
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4196 - 4212
[4] Patent: US2015/203498, 2015, A1, . Location in patent: Paragraph 0167; 0168
[5] Patent: WO2016/185342, 2016, A1, . Location in patent: Page/Page column 39
[6] Journal of Medicinal Chemistry, 1987, vol. 30, # 11, p. 2031 - 2046
[7] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 7, p. 585 - 589
[8] Patent: WO2009/24585, 2009, A2, . Location in patent: Page/Page column 67
[9] Patent: WO2014/9305, 2014, A1, . Location in patent: Page/Page column 31
  • 2
  • [ 6863-73-6 ]
  • [ 126-38-5 ]
  • [ 85333-43-3 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: With hydrogenchloride In water at 90℃; for 0.25 h;
Stage #2: With sodium hydrogencarbonate In water at 20℃;
Stage #3: at 90℃; for 2.5 h;
A mixture of l-bromo-2, 2-dimethoxypropane (42.4 g, 231.5 mmol) and conc. HC1 (890 uL, 28.9 mmol) in water (6.25 mL) was heated to 90°C, for 15 min, cooled to r. t. and quenched with NaHC03. 2-Amino-3-chloropyrazine (Compound I in Scheme 1,0. 2 g, 1.54 mmol) was added and the resultant mixture was heated to 90°C for 2h 30 min. The cooled reaction mixture was partitioned between 2M NaHC03 aq (100 mL) and dichloromethane (100 mL). The aqueous layer was separated and extracted with dichloromethane (5 x 100 mL). The combined organic extracts were dried over anhydr. Na2S04 and concentrated in vacuo to yield the crude title compound. Purification by recrystallization from the minimum amount of hot dichloromethane provided 7.0 g (54 percent yield) of the pure title compound.'H NMR (CH30H-d4) 8 8. 38 (d, J 4. 5 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J4.5 Hz, 1H), 2.49 (s, 3H); MS (ESI) 167. 8 ([M+H] +, Cl35), 169.8 ([M+H] +, C137)
54%
Stage #1: With hydrogenchloride In water at 90℃; for 0.25 h;
Stage #2: With sodium hydrogencarbonate In water at 20℃;
Stage #3: at 90℃; for 2.5 h;
A mixture of l-bromo-2, 2-dimethoxypropane (42.4 g, 231.5 mmol) and conc. HC1 (890 uL, 28.9 mmol) in water (6.25 mL) was heated to 90°C, for 15 min, cooled to r. t. and quenched with NaHC03. 2-Amino-3-chloropyrazine (Compound I in Scheme 1,0. 2 g, 1.54 mmol) was added and the resultant mixture was heated to 90°C for 2h 30 min. The cooled reaction mixture was partitioned between 2M NaHC03 aq (100 mL) and dichloromethane (100 mL). The aqueous layer was separated and extracted with dichloromethane (5 x 100 mL). The combined organic extracts were dried over anhydr. Na2S04 and concentrated in vacuo to yield the crude title compound. Purification by recrystallization from the minimum amount of hot dichloromethane provided 7.0 g (54 percent yield) of the pure title compound.'H NMR (CH30H-d4) 8 8. 38 (d, J 4. 5 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J4.5 Hz, 1H), 2.49 (s, 3H); MS (ESI) 167. 8 ([M+H] +, Cl35), 169.8 ([M+H] +, C137)
Reference: [1] Patent: WO2005/34837, 2005, A2, . Location in patent: Page/Page column 41
[2] Patent: WO2005/34837, 2005, A2, . Location in patent: Page/Page column 41
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