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[ CAS No. 40611-79-8 ] {[proInfo.proName]}

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Chemical Structure| 40611-79-8
Chemical Structure| 40611-79-8
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Product Details of [ 40611-79-8 ]

CAS No. :40611-79-8 MDL No. :MFCD02179575
Formula : C7H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MIBDQVZPRVDXQP-UHFFFAOYSA-N
M.W : 153.14 Pubchem ID :640310
Synonyms :

Calculated chemistry of [ 40611-79-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.14
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.46
TPSA : 59.16 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 0.36
Log Po/w (WLOGP) : 0.61
Log Po/w (MLOGP) : -0.57
Log Po/w (SILICOS-IT) : 1.39
Consensus Log Po/w : 0.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.15
Solubility : 10.7 mg/ml ; 0.07 mol/l
Class : Very soluble
Log S (Ali) : -1.17
Solubility : 10.4 mg/ml ; 0.0681 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.62
Solubility : 3.71 mg/ml ; 0.0242 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 40611-79-8 ]

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

Application In Synthesis of [ 40611-79-8 ]

* 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 [ 40611-79-8 ]
  • Downstream synthetic route of [ 40611-79-8 ]

[ 40611-79-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 40611-79-8 ]
  • [ 2818-07-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 657 - 661
  • 2
  • [ 1193-62-0 ]
  • [ 68-12-2 ]
  • [ 40611-79-8 ]
  • [ 1197-13-3 ]
YieldReaction ConditionsOperation in experiment
48.18% at 0 - 20℃; To the stirred solution of methyl 1H-pyrrole-2-carboxylate (0.9 g, 7.19 mmol) in DMF (4.2 g, 57.52 mmol) at 0 00, POOl3 (5.5 g, 35.96 mmol) was added. The reaction mixture was stirred at 10 00 for 30 mm at room temperature over night. The reaction mixture was quenched with sodium hydroxide solution and extracted using ethyl acetate dried over anhydrous Na2SO4. The crude mixture of products was purified by column chromatography to yield the title compound polar spot (0.53 g, 48.18percent) as a pale yellow solid. LCMS: (M-H) = 152.1; 1H NMR: (DMSO-d6, 300MHz) 6 12.73 (5, 1H), 7.76 (5, 1H), 7.82-7.83 (d, 1H), 7.14 (5, 2H), 3.81 (5, 3H). Intermediate 12a: Methyl 5-formyl-1H-pyrrole-2-carboxylate was formed along with11 a. Upon separation of 11 a and 1 2a, intermediate 1 2a obtained (0.5 g, 45.45percent) asa pale yellow solid. LOMS: (M-H) = 152.1
Reference: [1] Tetrahedron, 1992, vol. 48, # 8, p. 1457 - 1464
[2] Tetrahedron, 2001, vol. 57, # 15, p. 3063 - 3067
[3] European Journal of Organic Chemistry, 2008, # 2, p. 324 - 329
[4] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 84; 85
[5] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4631 - 4634
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 2935 - 2937
[7] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5763 - 5773
  • 3
  • [ 1193-62-0 ]
  • [ 40611-79-8 ]
  • [ 1197-13-3 ]
Reference: [1] Patent: EP1568698, 2005, A1, . Location in patent: Page/Page column 45-46
[2] Patent: WO2008/89453, 2008, A2, . Location in patent: Page/Page column 94-95
  • 4
  • [ 40611-79-8 ]
  • [ 74-88-4 ]
  • [ 67858-47-3 ]
YieldReaction ConditionsOperation in experiment
95.72%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25 h;
Stage #2: at 20℃; for 0.5 h;
To a solution of methyl 4-formyl-1H-pyrrole-2-carboxylate (0.15 g, 098 mmol) in DMF(4 mL) at 0 00 NaH (0.047 g (95percent), 1.96 mmol) was added and stirred at 0 00 for 15mm. Then methyl iodide (0.208 g, 1 .47 mmol) was added to it and stirred at roomtemperature for 30 mm. The reaction mixture was quenched with water and extractedusing ethyl acetate dried over anhydrous Na2SO4 and concentrated to yield the title compound (0.16 g, 95.72percent) as a pale brown solid. LCMS: (M+H) = 168.1; 1H NMR:(DMSO-d6, 300MHz) 69.71(s, 1H), 7.91(s, 2H), 7.22-7.23 (d, 2H), 3.92 (5, 3H), 3.78 (5, 3H).
95.72%
Stage #1: With sodium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.25 h;
Stage #2: at 20℃; for 0.5 h;
To a solution of methyl 4-formyl-1H-pyrrole-2-carboxylate (0.15 g, 098 mmol) in DMF(4 mL) at 0 00 NaOH (0.047 g (95percent), 1 .96 mmol) was added and stirred at 0 00 for15 mm. Then methyl iodide (0.208 g, 1 .47 mmol) was added and stirred at roomtemperature for 30 mm. The reaction mixture was quenched with water and extractedusing ethyl acetate dried over anhydrous Na2SO4 and concentrated to yield the titlecompound (0.16 g, 95.72percent) as a pale brown solid. LOMS: (M+H) = 168.1; 1H NMR:(DMSO-d6, 300MHz) 6 9.71 (5, 1 H), 7.91 (5, 2H), 7.22-7.23 (d, 2H), 3.92 (5, 3H), 3.78 (5, 3H).
Reference: [1] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 85
[2] Patent: WO2014/202528, 2014, A1, . Location in patent: Page/Page column 73
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