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[ CAS No. 27006-76-4 ] {[proInfo.proName]}

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Chemical Structure| 27006-76-4
Chemical Structure| 27006-76-4
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Product Details of [ 27006-76-4 ]

CAS No. :27006-76-4 MDL No. :MFCD00052538
Formula : C6H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :SZRSMNYUEXXEBL-UHFFFAOYSA-N
M.W : 158.59 Pubchem ID :2777397
Synonyms :

Calculated chemistry of [ 27006-76-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.85
TPSA : 34.89 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) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 1.06
Log Po/w (WLOGP) : 1.19
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.12

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.8
Solubility : 2.54 mg/ml ; 0.016 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 6.55 mg/ml ; 0.0413 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.74
Solubility : 2.91 mg/ml ; 0.0184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 27006-76-4 ]

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 [ 27006-76-4 ]

* 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 [ 27006-76-4 ]
  • Downstream synthetic route of [ 27006-76-4 ]

[ 27006-76-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 68-11-1 ]
  • [ 27006-76-4 ]
  • [ 25252-46-4 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1969, vol. 5, p. 567[2] Khimiya Geterotsiklicheskikh Soedinenii, 1969, vol. 5, # 4, p. 760 - 761
  • 2
  • [ 68-12-2 ]
  • [ 2749-59-9 ]
  • [ 27006-76-4 ]
YieldReaction ConditionsOperation in experiment
81.5%
Stage #1: at 0 - 10℃; for 0.5 h;
Stage #2: at 80 - 90℃; for 4 h;
2,5-Dimethyl-2,4-dihydro-3H-pyrazol-3-one 4 was prepared byrefluxing ethyl acetoacetate and methylhydrazine in ethanol.5Intermediate pyrazole carbaldehyde 5was prepared according toreference30 and the method was improved. To a violently stirredcold solution of DMF (23 mL) was added dropwise phosphorusoxychloride (64 mL) at 0–10°C. The mixture was stirred at thistemperature for 30min then compound 4 (0.1 mol) was addedin portions. The mixture was heated to 80–90°C and stirred for4 h. After being cooled to room temperature, the mixture waspoured into ice water (350 mL) and stirred for 10 min, thenextracted with ethyl acetate (3 × 25 mL). The organic layer waswashed with saturated NaHCO3 solution (2×15 mL) and brine(15 mL) successively, and dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure, the residue wasrecrystallized from ethyl acetate/petroleum ether (60–90°C) togive pyrazole carbaldehyde 5 as light yellow crystals, mp 77–78°C, yield 81.5percent (Lit30 mp 78–79°C).
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 1, p. 34 - 41
[2] Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1309 - 1313
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 13, p. 3307 - 3312
[4] Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 10, p. 3636 - 3640
[5] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2010, vol. 75, # 5, p. 1501 - 1505
[6] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 2, p. 389 - 396
[7] Molecules, 2012, vol. 17, # 5, p. 5139 - 5150
[8] Organic Letters, 2015, vol. 17, # 4, p. 932 - 935
  • 3
  • [ 3201-29-4 ]
  • [ 68-12-2 ]
  • [ 27006-76-4 ]
YieldReaction ConditionsOperation in experiment
62% at 0 - 100℃; for 7 h; Step 2: Synthesis of 5-chloro-l,3-dimethyl-lH-pyrazole-4-carbaldehyde: [0713] To a mixture of 2,5-dimethyl-lH-pyrazol-3(2H)-one (32 g, 285.71 mmol) and POCl3 (128 mL) at 0 °C, DMF (26.35 mL, 342.85 mmol) was added slowly. The resulting reaction mixture was stirred at 100 °C for 7 h. The progress of the reaction was monitored by TLC. On completion, the reaction mixture was concentrated to dryness under reduced pressure. The residue obtained was basified with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were dried over anhydrous a2S04 and concentrated under reduced pressure to afford the crude material which then purified by column chromatography giving the title compound (28 g, 62.0percent).
45.7%
Stage #1: at 0℃; for 0.333333 h;
Stage #2: at 80 - 90℃; for 5 h;
0.35 mol of DMF was added to a 250 mL three-necked flask, and 0.83 mol of POCl3 was slowly added dropwise at 0 ° C,After stirring for 20 min, 0.10 mol 1,3-dimethyl-5-pyrazolone was slowly added and the temperature was raised to 80-90 ° C. Reaction 5H, after cooling slowly into the 200 mL of ice water, standing 2 h, suction filtration, washing, drying, in yellow solid; yield: 45.7percent.
Reference: [1] Patent: WO2015/10049, 2015, A1, . Location in patent: Paragraph 0712; 0713
[2] Patent: WO2015/200650, 2015, A1, . Location in patent: Paragraph 0519; 0522-0523
[3] Patent: CN103951663, 2016, B, . Location in patent: Paragraph 0221; 0224; 0225
  • 4
  • [ 5203-77-0 ]
  • [ 68-12-2 ]
  • [ 27006-76-4 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: at 20℃; for 0.333333 h;
Stage #2: at 80℃;
General procedure: Phosphorus oxychloride (0.07 mol) was added dropwise to ice cooled N,N-dimethylformamide (0.03 mol) and then stirred for 20 min at room temperature. Compound 2a or 2b (0.02 mol) was added to the mixture and reacted for 1-5 h at 80 °C. After cooling, poured the reaction mixture was poured into 50 ml ice/water mixture, ensuring the mixture temperature to be below 35 °C. Dichloromethane (30 mL x 3) was used to extract the aqueous layer. Then anhydrous MgSO4 was used to dry the combined layer of dichloromethane. A yellow solid 3a or 3b was obtained after the evaporation of the solvent under 35 °C. The compound 3a obtained gave the yield of 56 percent, and the melting point of 3a was determined as 76-77 °C (The melting point in the reference [18] was 78-79 °C). The compound 3b obtained gave the yield of 52percent, and the melting point of 3b was determined as 61-62 °C (63 °C was reported in the reference [18]).
Reference: [1] Letters in Drug Design and Discovery, 2016, vol. 13, # 8, p. 800 - 808
  • 5
  • [ 68-12-2 ]
  • [ 27006-76-4 ]
Reference: [1] Patent: WO2005/75433, 2005, A1, . Location in patent: Page/Page column 178-179
  • 6
  • [ 68-12-2 ]
  • [ 27006-76-4 ]
  • [ 25016-12-0 ]
  • [ 26990-64-7 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 9, p. 1541 - 1550
  • 7
  • [ 27006-76-4 ]
  • [ 78703-53-4 ]
Reference: [1] Australian Journal of Chemistry, 1983, vol. 36, # 1, p. 135 - 147
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