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[ CAS No. 37619-24-2 ] {[proInfo.proName]}

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Chemical Structure| 37619-24-2
Chemical Structure| 37619-24-2
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Product Details of [ 37619-24-2 ]

CAS No. :37619-24-2 MDL No. :MFCD00052747
Formula : C7H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :APHVGKYWHWFAQV-UHFFFAOYSA-N
M.W : 139.15 Pubchem ID :142178
Synonyms :

Calculated chemistry of [ 37619-24-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.97
TPSA : 31.23 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) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 1.8
Log Po/w (WLOGP) : 0.81
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 0.63
Consensus Log Po/w : 1.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.07
Solubility : 1.17 mg/ml ; 0.00842 mol/l
Class : Soluble
Log S (Ali) : -2.07
Solubility : 1.17 mg/ml ; 0.00842 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.22
Solubility : 8.42 mg/ml ; 0.0605 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 37619-24-2 ]

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

Application In Synthesis of [ 37619-24-2 ]

* 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 [ 37619-24-2 ]
  • Downstream synthetic route of [ 37619-24-2 ]

[ 37619-24-2 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 37619-24-2 ]
  • [ 6973-60-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 11, p. 2422 - 2435
[2] Journal of Physical Chemistry A, 2002, vol. 106, # 44, p. 10613 - 10621
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 11, p. 3219 - 3223
  • 2
  • [ 1193-62-0 ]
  • [ 74-88-4 ]
  • [ 37619-24-2 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5 h;
Stage #2: at 20℃; for 17 h;
To a mixture of methyl- lH-pyrrole-2-carboxylate (10 g, 79.9 mmol) in anhydrous THF (200 mL) was added NaH (3.52 g, 60percent w.t., 87.9 mmol) at 0°C. The resulting mixture was stirred at 20°C for 30 min, then CH3I (13.62 g, 95.9 mmol) was added. The reaction mixture was stirred at 20°C for 17 hrs. The mixture was then poured into an aqueous solution of NH4CI (200 mL). The aqueous layer was extracted with EtOAc (200 mL x 2). The combined organic layers were washed with brine (150 mL), dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by chromatography (silica, EtOAc/PE = 1/20) to afford methyl 1 -methyl- lH-pyrrole-2- carboxylate (9.88 g, 71 mmol, 89 percent) as a yellow oil. MS (EI+, m/z): 140.1 [M+H]+.
Reference: [1] Organic Letters, 2015, vol. 17, # 11, p. 2652 - 2655
[2] Patent: WO2018/89493, 2018, A1, . Location in patent: Paragraph 00214
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 11, p. 3219 - 3223
  • 3
  • [ 6973-60-0 ]
  • [ 74-88-4 ]
  • [ 37619-24-2 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1989, vol. 78, # 11, p. 910 - 917
[2] Patent: US4256759, 1981, A,
[3] Patent: US4256759, 1981, A,
  • 4
  • [ 1193-62-0 ]
  • [ 616-38-6 ]
  • [ 37619-24-2 ]
Reference: [1] Organic Process Research and Development, 2009, vol. 13, # 6, p. 1199 - 1201
  • 5
  • [ 616-38-6 ]
  • [ 634-97-9 ]
  • [ 37619-24-2 ]
Reference: [1] Organic Process Research and Development, 2009, vol. 13, # 6, p. 1199 - 1201
  • 6
  • [ 106115-97-3 ]
  • [ 37619-24-2 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 55 - 60
  • 7
  • [ 190783-99-4 ]
  • [ 37619-24-2 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 55 - 60
[2] Chemische Berichte, 1987, vol. 120, p. 55 - 60
[3] Chemische Berichte, 1987, vol. 120, p. 55 - 60
[4] Chemische Berichte, 1987, vol. 120, p. 55 - 60
[5] Chemische Berichte, 1987, vol. 120, p. 55 - 60
[6] Chemische Berichte, 1987, vol. 120, p. 55 - 60
[7] Chemische Berichte, 1987, vol. 120, p. 55 - 60
[8] Chemische Berichte, 1987, vol. 120, p. 55 - 60
  • 8
  • [ 6973-60-0 ]
  • [ 7087-68-5 ]
  • [ 37619-24-2 ]
Reference: [1] Patent: US4675186, 1987, A,
  • 9
  • [ 67-56-1 ]
  • [ 6973-60-0 ]
  • [ 18107-18-1 ]
  • [ 37619-24-2 ]
Reference: [1] Patent: US2007/259924, 2007, A1, . Location in patent: Page/Page column 33
  • 10
  • [ 96-54-8 ]
  • [ 67-56-1 ]
  • [ 56-23-5 ]
  • [ 37619-24-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 2010, vol. 46, # 7, p. 1053 - 1059
  • 11
  • [ 1200-94-8 ]
  • [ 37619-24-2 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 55 - 60
[2] Chemische Berichte, 1987, vol. 120, p. 55 - 60
  • 12
  • [ 106115-97-3 ]
  • [ 37619-24-2 ]
  • [ 1198-07-8 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 55 - 60
  • 13
  • [ 13515-93-0 ]
  • [ 1611-78-5 ]
  • [ 37619-24-2 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 31, p. 4150 - 4152
  • 14
  • [ 186581-53-3 ]
  • [ 6973-60-0 ]
  • [ 37619-24-2 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 225,228
[2] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1475 - 1480
  • 15
  • [ 96-54-8 ]
  • [ 37619-24-2 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 225,228
  • 16
  • [ 1192-58-1 ]
  • [ 67-56-1 ]
  • [ 37619-24-2 ]
Reference: [1] Chemical Science, 2016, vol. 7, # 7, p. 4428 - 4434
  • 17
  • [ 1193-62-0 ]
  • [ 37619-24-2 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 4458,4462
  • 18
  • [ 634-97-9 ]
  • [ 37619-24-2 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 4458,4462
  • 19
  • [ 37619-24-2 ]
  • [ 77716-11-1 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1989, vol. 78, # 11, p. 910 - 917
  • 20
  • [ 37619-24-2 ]
  • [ 4885-02-3 ]
  • [ 67858-47-3 ]
YieldReaction ConditionsOperation in experiment
98% With aluminum (III) chloride In nitromethane; 1,2-dichloro-ethane at -25℃; for 0.5 h; To a mixture of methyl- 1 -methyl- lH-pyrrole-2-carboxylate (10 g, 71.86 mmol), AlCb (21.08 g, 158.1 mmol) in 1,2-dichloroethane (100 mL), and MeN02 (100 mL) was added a solution of dichloro(methoxy)methane (8.26 g, 71.86 mmol) at -25°C. The resulting mixture was stirred at -25°C for 0.5 hr. The mixture was then poured into ice (100 mL). The mixture was partitioned between CH2CI2 (100 mL) and H20 (100 mL). The layers were separated. The CH2CI2 layer was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by chromatography (silica, EtOAc/PE = 1/1) to afford methyl 4-formyl-l -methyl- lH-pyrrole-2- carboxylate (11.77 g, 70.42 mmol, 98percent) as a yellow solid. MS (EI+, m/z): 168.2 [M+H]+. MR (400 MHz, DMSO-^) δ 9.71 (s, 1H), 7.91 (d, J= 1.8 Hz, 1H), 7.22 (d, J= 1.8 Hz, 1H), 3.92 (s, 3H), 3.78 (s, 3H). NOESY confirmed this structure.
Reference: [1] Patent: WO2018/89493, 2018, A1, . Location in patent: Paragraph 00215
[2] Medicinal Chemistry Research, 1995, vol. 5, # 6, p. 426 - 430
  • 21
  • [ 37619-24-2 ]
  • [ 68-12-2 ]
  • [ 67858-47-3 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Inert atmosphere
Stage #2: at 20℃; for 16 h;
To a solution of methyl- 1 -methyl- lH-pyrrole-2-carboxylate (10.0 g, 71.86 mmol) in THF (200 mL) at -78°C was added n-BuLi (31.6 mL, 79.05 mmol) under nitrogen. The mixture was stirred at -78°C for 2 hrs. DMF (10.49 g, 143.72 mmol) was then added and the mixture was stirred for an additional 16 hrs while allowed to warm to rt. The mixture was then quenched with H20 (500 mL) and extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered, concentrated, and purified by chromatography (silica, EtOAc/PE = 1/8) to afford methyl 4-formyl- 1 -methyl- lH-pyrrole-2-carboxylate (6.37g, 38.09 mmol, 53percent) as an oil. ESI-MS (EI+, m/z): 168.3 [M+H]+.
Reference: [1] Patent: WO2018/89493, 2018, A1, . Location in patent: Paragraph 00399
  • 22
  • [ 37619-24-2 ]
  • [ 67858-47-3 ]
Reference: [1] Patent: US4380645, 1983, A,
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