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[ CAS No. 2199-58-8 ] {[proInfo.proName]}

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Chemical Structure| 2199-58-8
Chemical Structure| 2199-58-8
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Product Details of [ 2199-58-8 ]

CAS No. :2199-58-8 MDL No. :MFCD00111522
Formula : C7H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :RDFZYUOHJBXMJA-UHFFFAOYSA-N
M.W : 123.15 Pubchem ID :270465
Synonyms :

Calculated chemistry of [ 2199-58-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.29
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.11
TPSA : 32.86 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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 0.17
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 1.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.75
Solubility : 2.2 mg/ml ; 0.0178 mol/l
Class : Very soluble
Log S (Ali) : -1.56
Solubility : 3.4 mg/ml ; 0.0276 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.639 mg/ml ; 0.00519 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 2199-58-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2199-58-8 ]

* 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 [ 2199-58-8 ]
  • Downstream synthetic route of [ 2199-58-8 ]

[ 2199-58-8 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 625-82-1 ]
  • [ 2199-58-8 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: at 0℃; for 0.333333 h;
Stage #2: at 0℃; for 0.5 h; Heating / reflux
Stage #3: With sodium acetate In 1,2-dichloro-ethane for 0.333333 h; Heating / reflux
A.
2-formyl-3,5-dimethylpyrrole
To dimethylformamide (4.5 mL, 57.8 mmol) under argon at 0° C. was added phosphorus oxychloride (57.8 mmol) dropwise over 5 min.
The cooling bath was removed and after 15 min. 1,2-dichloroethane (15 mL) was added.
The reaction mixture was again cooled to 0° C. and a solution of 2,4-dimethylpyrrole (52.6 mmol) in 1,2-dichloroethane (15 mL) was added dropwise over 15 min.
The reaction was heated to reflux for 15 min, and then cooled to rt.
A solution of sodium acetate (24 g) in water (75 mL) was added slowly to the reaction mixture and the resulting mixture was again heated to reflux for 20 min.
After the reaction mixture was cooled to rt it was diluted with CH2Cl2, and the aqueous phase was washed with CH2Cl2 (2*50 mL).
The combined organic fractions were washed with saturated NaHCO3, dried (Na2SO4), and concentrated in vacuo.
The crude material was purified by chromatography on silica gel eluding with 10percent ethyl acetate in hexane to provide 5.2 g (80percent) of the desired compound 2-formyl-3,5-dimethylpyrrole. [M+H]+=124.1, [M-H]-=122.0
Reference: [1] Patent: US6982265, 2006, B1, . Location in patent: Page/Page column 28
[2] Gazzetta Chimica Italiana, 1934, vol. 64, p. 778,782
  • 2
  • [ 625-82-1 ]
  • [ 68-12-2 ]
  • [ 2199-58-8 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 0 - 20℃; Inert atmosphere
Stage #2: at 0 - 40℃; Inert atmosphere
POCl3 (1.00mL, 11 mmol) was added dropwise at 0°C to DMF (20mL) and the resulting mixture was stirred for 5min. The solution was then stirred at rt for 30min before being cooled back down to 0°C. The solution was then treated with 3,5-dimethyl-1H-pyrrole (1.0mL, 10mmol). The resulting mixture was allowed to warm up to rt, and then heated to 40°C until completion as indicated by TLC analysis (18h). The reaction was then cooled down to rt and diluted with EtOAc (30mL). The resulting solution was washed with H2O (8×50mL), brine (3×50mL), dried (Na2SO4) and concentrated in vacuo to afford the crude as a dark brown solid. Column chromatography (silica gel, 50percent Et2O/petroleum ether) afforded (1.1g, 82percent) of the desired pyrrole carbaldehyde 8 as an off white solid. 1H NMR (CDCl3, 400MHz) δ: 10.14 (1H, br s), 9.49 (1H, s), 5.89 (1H, s), 2.32 (3H, s), 2.30 (3H, s). 13C NMR (CDCl3, 100MHz) δ: 176.0, 138.5, 134.8, 128.8, 112.1, 13.2, 10.5.
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 21, p. 4829 - 4841
[2] Chemical Communications, 2008, # 40, p. 4933 - 4935
[3] Tetrahedron, 2013, vol. 69, # 39, p. 8527 - 8533
[4] Russian Journal of General Chemistry, 2010, vol. 80, # 11, p. 2374 - 2381
[5] Russian Journal of General Chemistry, 2013, vol. 83, # 8, p. 1571 - 1579[6] Zh. Obshch. Khim., 2013, vol. 83, # 8, p. 1342 - 1350,9
  • 3
  • [ 625-82-1 ]
  • [ 75-34-3 ]
  • [ 2199-58-8 ]
Reference: [1] Patent: US6147106, 2000, A,
  • 4
  • [ 625-82-1 ]
  • [ 127-09-3 ]
  • [ 2199-58-8 ]
Reference: [1] Dalton Transactions, 2012, vol. 41, # 34, p. 10199 - 10210
  • 5
  • [ 625-82-1 ]
  • [ 74-90-8 ]
  • [ 2199-58-8 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1949[2] Chemische Berichte, 1923, vol. 56, p. 520,523
[3] Chemische Berichte, 1922, vol. 55, p. 1949[4] Chemische Berichte, 1923, vol. 56, p. 520,523
[5] Journal of the American Chemical Society, 1941, vol. 63, p. 1829,1831
  • 6
  • [ 2436-79-5 ]
  • [ 2199-58-8 ]
Reference: [1] Journal of the American Chemical Society, 1941, vol. 63, p. 1829,1831
  • 7
  • [ 625-82-1 ]
  • [ 68-12-2 ]
  • [ 2199-58-8 ]
  • [ 2199-61-3 ]
Reference: [1] Rend.Accad.Bologna, 1956, vol. <11>3, p. 16,22
  • 8
  • [ 4513-93-3 ]
  • [ 149-73-5 ]
  • [ 2199-58-8 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 24, p. 4602 - 4609
  • 9
  • [ 2199-44-2 ]
  • [ 2199-58-8 ]
Reference: [1] Russian Journal of General Chemistry, 2010, vol. 80, # 11, p. 2374 - 2381
[2] Russian Journal of General Chemistry, 2013, vol. 83, # 8, p. 1571 - 1579[3] Zh. Obshch. Khim., 2013, vol. 83, # 8, p. 1342 - 1350,9
  • 10
  • [ 103096-16-8 ]
  • [ 2199-58-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1958, vol. 619, p. 80,90
  • 11
  • [ 856197-93-8 ]
  • [ 2199-58-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1958, vol. 619, p. 80,90
  • 12
  • [ 856100-23-7 ]
  • [ 2199-58-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1934, vol. 64, p. 778,782
  • 13
  • [ 625-82-1 ]
  • [ 77287-34-4 ]
  • [ 2199-58-8 ]
Reference: [1] Bulet.Soc.Chim.Romania, 1929, vol. 11, p. 135,138
  • 14
  • [ 625-82-1 ]
  • [ 149-73-5 ]
  • [ 2199-58-8 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 35, p. 11327 - 11334
  • 15
  • [ 21898-46-4 ]
  • [ 2199-58-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1934, vol. 64, p. 778,782
  • 16
  • [ 625-82-1 ]
  • [ 68-12-2 ]
  • [ 10025-87-3 ]
  • [ 2199-58-8 ]
  • [ 2199-61-3 ]
Reference: [1] Rend. Accad. Bologna, 1956, vol. <11> 3, p. 16,22
  • 17
  • [ 2199-58-8 ]
  • [ 89909-51-3 ]
YieldReaction ConditionsOperation in experiment
92% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethaneHeating / reflux General procedure 6: To a suspension or solution of the starting pyrrole (1 eq. ) in CC14 is added NBS (1.05 eq. ) followed by benzoyl-peroxide (0.025 eq. ) under argon. The mixture is then heated to reflux and the reaction is followed by LC/MS. The crude mixture is then allowed to come to room temperature and cooled in an ice bath. A precipitate forms which is filtered and purified by flash chromatography. If no precipitation occurs the solvent is removed under reduced pressure and the crude is purified by flash chromatography. Preparation 23: 4-Bromo-3, 5-dimethyl-lH-pyrrole-2-carbaldehyde The general procedure 6 was followed using 3, 5-dimethyl-lH-pyrrole-2-carbaldehyde (8 g, 65 mmoles), NBS (12.16 g, 68.3 mmoles) and benzoyl-peroxide (394 mg, 1.63 mmole) in CC14 (300 mL). After purification 11.9 g of 4-bromo-3, 5-dimethyl-lH-pyrrole-2-carbaldehyde were obtained as a dark solid (92percent yield). 1H NMR (DMSO-d6) 8 12.06 (br, lH), 9.50 (s, lH), 2.22 (s, 3H), 2.19 (s, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 17, p. 5412 - 5414
[2] Patent: WO2005/58309, 2005, A1, . Location in patent: Page/Page column 62
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7286 - 7309
  • 18
  • [ 2199-58-8 ]
  • [ 40236-20-2 ]
YieldReaction ConditionsOperation in experiment
98% at -8 - 20℃; for 0.666667 h; Starting material 2-formyl-3,5-dimethyl-1-hydropyrrole (5.0 g, 1.0e) was added in portions to concentrated sulfuric acid (60 ml), kept at a temperature of 0 to -5 °C. The mixture was a reddish brown clear liquid, to which was added potassium nitrate (4.35 g, 1.05 e) in portions, kept at a temperature of -8 to -2 °C. After the addition, the mixture was reacted at about -7 °C for 20 min, then was warmed to room temperature and reacted for 20 min. Once the reaction was completed as indicated by TLC, the reaction solution was added into 1500 ml of ice water, and an earthy yellow solid was precipitated. The precipitate was collected by filtration, washed with water to neutral, and dried to obtain a grey product, 6.7 g (yield 98percent).
98% at -8 - 20℃; for 0.666667 h; a.
Synthesis of 2-formyl-3,5-dimethyl-4-nitro-1-hydropyrrole
Starting material 2-formyl-3,5-dimethyl-1-hydropyrrole (5.0 g, 1.0e) was added in portions to concentrated sulfuric acid (60 ml), kept at a temperature of 0 to -5° C.
The mixture was a reddish brown clear liquid, to which was added potassium nitrate (4.35 g, 1.05 e) in portions, kept at a temperature of -8 to -2° C.
After the addition, the mixture was reacted at about -7° C. for 20 min, then was warmed to room temperature and reacted for 20 min.
Once the reaction was completed as indicated by TLC, the reaction solution was added into 1500 ml of ice water, and an earthy yellow solid was precipitated.
The precipitate was collected by filtration, washed with water to neutral, and dried to obtain a grey product, 6.7 g (yield 98percent).
98% at -7 - 20℃; for 0.666667 h; General procedure: 2-formyl-3,5-dimethyl-1-hydropyrrole (5.0 g, 40 mmol) wasadded in portions to 60 ml of concentrated sulfuric acid andstirred at 0C to generate a reddish brown clear liquid. Potassiumnitrate (4.35 g, 43 mmol) was added into the mixture in portionsat 7 C. After the addition, the mixture was stirred at 7 C for20 min, then was warmed to room temperature and reacted for20 min. Once the reaction was completed as indicated by TLC, thereaction solution was added into 1500 ml of ice water, and anearthy yellowsolid was precipitated. The precipitate was collectedby filtration, washed with water to neutral, and dried to give 2-formyl-3,5-dimethyl-4-nitro-1-hydropyrrole as a gray product(6.7 g, yield 98percent)
5 g at -10℃; for 4 h; 3,5-dimethyl-2-pyrrolealdehyde I as a raw material (5 g, 40 mmol) was dissolved in 60 mL concentrated sulfuric acid, then the temperature of the system was lowered to —10° C., at which temperature KNO3 (4.35 g, 42 mmol) was slowly added in batches over about 2 h, during which the temperature was maintained at —10° C., and the solution was further stirred for about 2 h at this temperature after the addition of KNO3 was completed. Upon completion of the reaction as indicated by TLC, the resultant solution was added to 1 pL ice water, and extracted twice with a total of 1 L ethyl acetate. The organic layer was washed with a saturated NaC1 solution, dried over anhydrous sodium sulfate, and filtered. Then the organic solvents were evaporated oil at reduced pressure to obtain 7 g crude product, which was added to 10-20 mL ethyl acetate, followed by vigorous stirring, to obtain 5 g pure product of the target compoundII.
6.7 g at -2 - 20℃; for 0.333333 h; The crude 2-aldehyde-3,5-dimethyl-1-hydrogenpyrrole (5.0 g, 1.0 ) was added portionwise to concentrated sulfuric acid (60 ml) at a temperature of 0 ° C to 5 ° C, , Potassium nitrate (4.358, 1.056) was added in portions and the temperature was maintained at -8 to 2 ° C, after the addition, -7 ° C reaction 20min, rose to room temperature reaction 20min, TLC detection reaction is completed, the reaction solution added to 1500ml ice water, the precipitate yellow solid, filtered, washed to neutral, dry gray product 6.7g (yield 98percent)

Reference: [1] Patent: EP2581371, 2013, A1, . Location in patent: Paragraph 0071; 0072
[2] Patent: US2013/158030, 2013, A1, . Location in patent: Paragraph 0113; 0114
[3] European Journal of Medicinal Chemistry, 2014, vol. 82, p. 139 - 151
[4] Synthetic Communications, 2008, vol. 38, # 17, p. 3017 - 3022
[5] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 72 - 86
[6] Patent: US2016/347740, 2016, A1, . Location in patent: Paragraph 0026; 0027
[7] Patent: CN103130774, 2016, B, . Location in patent: Paragraph 0063-0065
[8] Patent: CN108727341, 2018, A, . Location in patent: Paragraph 0088; 0090; 0091; 0092
  • 19
  • [ 2199-58-8 ]
  • [ 59-48-3 ]
  • [ 194413-58-6 ]
YieldReaction ConditionsOperation in experiment
86% With piperidine In methanolReflux General procedure: To a solution of indolin-2-one (compound 1) (200 mg, 1eq.) in MeOH (5 mL), piperidine (1.5 eq.), and correspondingaldehydes (2a–2k) (1.2 eq.) were added. Thereaction mixture was heated to reflux and stirred for 1–4 h,then cooled to room temperature. The mixture was filtered,and the filter cake was washed with MeOH three times, thenthe filter cake was collected and dried under vacuum toremove MeOH to give the desired compounds 3a–3k.
Reference: [1] Journal of Antibiotics, 2018, vol. 71, # 10, p. 887 - 897
[2] Tetrahedron, 2009, vol. 65, # 25, p. 4894 - 4903
[3] ChemMedChem, 2016, vol. 11, # 1, p. 72 - 80
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 14, p. 2588 - 2603
[5] Synthetic Communications, 2008, vol. 38, # 17, p. 3017 - 3022
  • 20
  • [ 2199-58-8 ]
  • [ 152302-94-8 ]
  • [ 194413-58-6 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 33, p. 6606 - 6612
  • 21
  • [ 110-89-4 ]
  • [ 2199-58-8 ]
  • [ 59-48-3 ]
  • [ 194413-58-6 ]
Reference: [1] Patent: US5834504, 1998, A,
[2] Patent: US5883116, 1999, A,
[3] Patent: US5883113, 1999, A,
[4] Patent: US6846839, 2005, B1,
  • 22
  • [ 2199-58-8 ]
  • [ 1243657-66-0 ]
  • [ 194413-58-6 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 33, p. 6606 - 6612
  • 23
  • [ 2199-58-8 ]
  • [ 59-48-3 ]
  • [ 204005-46-9 ]
YieldReaction ConditionsOperation in experiment
10.4 g With piperidine In methanol at 65℃; To a solution of 2-formyl-3,5-dimethylpyrrole (compound 27, 7.17 g) and indolin-2-one (5.0 g) in methanol (100 mL) was added piperidine (1.0 mL). The mixture was stirred at 65 °C overnight. After cooling down to room temperature, the resulting solid gave desired compound 29 (10.4 g) as a yellow solid.
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 10, p. 3086 - 3095
  • 24
  • [ 2199-58-8 ]
  • [ 17630-75-0 ]
  • [ 1055412-47-9 ]
YieldReaction ConditionsOperation in experiment
40% With piperidine In ethanol for 8 h; Heating / reflux A mixture of 5-chlorooxindole (6.98 g, 41.6 mmol), 3,5-dimethyl-1H-pyrrole-2-carboxaldehyde (5.12 g, 41.6 mmol) and piperidine (410 μL, 4.16 mmol) in 200 mL of EtOH was heated at reflux for 8 h. The reaction mixture was cooled to room temperature and filtered to give the title compound (4.50 g, 40percent) as a red/orange solid.
40% With piperidine In ethanol for 8 h; Heating / reflux A mixture of 5-chlorooxindole (6.98 g, 41.6 mmol), 3,5-dimethyl-1H-pyrrole-2-carboxaldehyde (5.12 g, 41.6 mmol) and piperidine (410 μL, 4.16 mmol) in 200 mL of EtOH was heated at reflux for 8 h.
The reaction mixture was cooled to room temperature and filtered to give the title compound (4.50 g, 40percent) as a red/orange solid.
Reference: [1] Patent: US2004/102509, 2004, A1, . Location in patent: Page 9
[2] Patent: US6699863, 2004, B1, . Location in patent: Page/Page column 16
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