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Product Details of [ 619-66-9 ]

CAS No. :619-66-9 MDL No. :MFCD00006951
Formula : C8H6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :GOUHYARYYWKXHS-UHFFFAOYSA-N
M.W : 150.13 Pubchem ID :12088
Synonyms :
Tetraphthalaldehydic acid

Calculated chemistry of [ 619-66-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.79
TPSA : 54.37 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) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.93
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 0.97
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 1.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.06 mg/ml ; 0.00706 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.454 mg/ml ; 0.00302 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.7
Solubility : 2.99 mg/ml ; 0.0199 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 619-66-9 ]

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 [ 619-66-9 ]

* 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 [ 619-66-9 ]
  • Downstream synthetic route of [ 619-66-9 ]

[ 619-66-9 ] Synthesis Path-Upstream   1~38

  • 1
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Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 100, p. 32 - 39
  • 2
  • [ 619-66-9 ]
  • [ 56-91-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6197 - 6208
  • 3
  • [ 99-94-5 ]
  • [ 6232-88-8 ]
  • [ 100-21-0 ]
  • [ 7697-26-9 ]
  • [ 619-66-9 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 4, p. 591 - 594[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 4, p. 681 - 685
  • 4
  • [ 99-94-5 ]
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  • [ 100-51-6 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 4, p. 583 - 591[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 4, p. 673 - 681
  • 5
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  • [ 100-21-0 ]
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  • [ 78504-88-8 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 4, p. 591 - 594[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 4, p. 681 - 685
  • 6
  • [ 619-66-9 ]
  • [ 1642-81-5 ]
Reference: [1] Organic Preparations and Procedures International, 2007, vol. 39, # 4, p. 412 - 415
[2] Chemistry - A European Journal, 2018, vol. 24, # 29, p. 7410 - 7416
  • 7
  • [ 99-94-5 ]
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  • [ 100-21-0 ]
  • [ 5162-82-3 ]
  • [ 3006-96-0 ]
  • [ 619-66-9 ]
  • [ 78504-88-8 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 4, p. 583 - 591[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 4, p. 673 - 681
  • 8
  • [ 99-94-5 ]
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  • [ 100-21-0 ]
  • [ 5162-82-3 ]
  • [ 3006-96-0 ]
  • [ 619-66-9 ]
  • [ 78504-88-8 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 4, p. 583 - 591[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 4, p. 673 - 681
  • 9
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  • [ 34040-64-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 12, p. 1964 - 1972
  • 10
  • [ 619-66-9 ]
  • [ 20576-82-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 10, p. 1491 - 1508
  • 11
  • [ 619-66-9 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
  • 12
  • [ 141-82-2 ]
  • [ 619-66-9 ]
  • [ 19675-63-9 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 28, p. 8673 - 8680
[2] Revue Roumaine de Chimie, 1999, vol. 44, # 3, p. 265 - 271
[3] Journal of the Chemical Society, 1928, p. 2576
[4] Journal of the Chemical Society, 1928, p. 2576
  • 13
  • [ 108-24-7 ]
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Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
  • 14
  • [ 619-66-9 ]
  • [ 19675-63-9 ]
Reference: [1] Chemische Berichte, 1912, vol. 45, p. 1586
[2] Justus Liebigs Annalen der Chemie, 1885, vol. 231, p. 363
  • 15
  • [ 619-66-9 ]
  • [ 38628-51-2 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 2576
[2] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 8, p. 846 - 852
  • 16
  • [ 18006-13-8 ]
  • [ 619-66-9 ]
  • [ 97364-15-3 ]
Reference: [1] Chemische Berichte, 1985, vol. 118, # 4, p. 1421 - 1440
  • 17
  • [ 619-66-9 ]
  • [ 124-40-3 ]
  • [ 58287-76-6 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With thionyl chloride In dichloromethane at 20℃; Inert atmosphere; Reflux
Stage #2: for 1.25 h; Cooling with ice-water
To a suspension of 4-formylbenzoic acid (4.00 g, 26.7 mmol) in dry DCM (8 mL) were added thionyl chloride (2.92 g, 40.0 mmol) and DMF (0.6 mL) dropwise at ambient temperature under nitrogen. The reaction mixture was refluxed for 2 h. After cooling, this mixture was added to 33percent dimethylamine in water (10.5 mL, 72 mmol) dropwise over 15 min in an ice-water bath, and the reaction mixture stirred for 1 h at the same temperature. The solvent was evaporated in vacuums. The residue was purified by chromatography on silica gel to give the title compound (2.5 g, yield 53percent) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.86 (s, 3H), 3.30 (s, 3H), 7.60 (d, J=7.6 Hz, 2H), 7.95 (d, J=7.6 Hz, 2H), 10.04 (s, 1H); LC-MS (ESI) m/z: 178 (M+1)+.
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 38, p. 12347 - 12351[2] Angew. Chem., 2018, vol. 130, # 38, p. 12527 - 12531,5
[3] Patent: US2010/35883, 2010, A1, . Location in patent: Page/Page column 80
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2334 - 2356
  • 18
  • [ 619-66-9 ]
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YieldReaction ConditionsOperation in experiment
53%
Stage #1: With thionyl chloride In dichloromethane for 2 h; Inert atmosphere; Reflux
Stage #2: With dimethyl amine In dichloromethane for 1.25 h; Cooling with ice
Example 101 A 4-Formyl-N,N-dimethylbenzamide[00685] To a suspension of 4-formylbenzoic acid (4.00 g, 26.7 mmol) in dry DCM (8 mL) were added thionyl chloride (2.92 g, 40.0 mmol) and DMF (0.6 mL) dropwise at ambient temperature under nitrogen. The reaction mixture was refluxed for 2 h. After cooling, this mixture was added to 33percent dimethylamine in water (10.5 mL, 72 mmol) dropwise over 15 min in an ice-water bath, and the reaction mixture stirred for 1 h at the same temperature. The solvent was evaporated in vacuums. The residue was purified by chromatography on silica gel to give the title compound (2.5 g, yield 53percent) as a yellow solid. ^-NMR (400 MHz, DMSO-i/6) 8(ppm): 2.86 (s, 3H), 3.30 (s, 3H), 7.60 (d, J= 7.6 Hz, 2H), 7.95 (d, J= 7.6 Hz, 2H), 10.04 (s, 1H); LC-MS (ESI) m/z: 178 (M+l)+.
Reference: [1] Patent: WO2011/130661, 2011, A1, . Location in patent: Page/Page column 153
  • 19
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Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 21, p. 4053 - 4061
[2] Patent: US4289769, 1981, A,
  • 20
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Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4344 - 4353
  • 21
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  • [ 36805-97-7 ]
  • [ 65874-27-3 ]
YieldReaction ConditionsOperation in experiment
81% for 1.5 h; Reflux To a solution of 4-formylbenzoic acid (1.0 g, 6.7 mmol) in refluxing benzene (12.6 mL, 0.50 M) was added 1,1-di-tert-butoxy-N,Ndimethylmethanamine (6.4 mL, 26.6 mmol, 4.0 equiv) over a period of 1 hr. The reaction was then allowed to continue refluxing for 30 mm before being cooled to rt and diluted with water. After washing with saturated sodium bicarbonate (2x), the combined organic layers were washed with brine,dried over MgSO4, filtered and concentrated in vacuo. The crude product was then purified using flash column chromatography on Si02 (Hexanes/EtOAc: 6/1) to yield a white solid (1.1 g, 81 percent).
57% at 20℃; Heating / reflux Step (2): synthesis of 4-formyl-benzoic acid tert-butyl ester:; 4-Formylbenzoic acid was suspended in 60 mL of benzene, and the mixture was placed under a nitrogen atmosphere. The mixture was brought to reflux and N,N -dimethylformamide di-tert-butylacetal was added dropwise via an addition funnel over 45 minutes. The yellowish suspension gradually turned golden yellow and became a homogeneous solution. The solution was refluxed an additional 60 minutes before stirring overnight at room temperature. The resulting orange solution was diluted to about 100 mL with ethyl acetate ("EtOAc"), and the resulting solution was washed sequentially with water, saturated sodium bicarbonate (2 x 100 mL), and brine (100 mL). The solvent was removed by rotary evaporation. The resulting amber oil was injected on to a BIOTAGE.(R). Flash 65i (350 g, silica gel) cartridge and purified with a 30-minute gradient of from 5percent to 25percent v/v EtOAc in heptane. Product fractions were pooled, and the solvent was rotary evaporated. The resulting golden oil was dried under house high vacuum overnight at room temperature to give 3.92 g (57percent yield) of 4- formyl-benzoic acid tert-butyl ester as a yellow solid; IH NMR (400 MHz, DMSO-D6) δ ppm 1.54 (s, 9 H) 8.00 (dm, /=8.30, Hz, 2 H) 8.07 (dm, /=8.30, 2 H) 10.08 (s, 1 H); Mass Spectrum MH" 206.
45% for 1.41667 h; Heating / reflux A solution of 4-carboxybenzaldehyde (15A) (0.35 g, 2.1 mmol) in toluene (9 mL) was heated to reflux and N,N-dimethylformamide di-tert-butyl-acetal (3.8 mL, 16.0 mmol) was added over 25 minutes. After the addition was complete, the reaction was stirred at reflux for an additional hour then cooled to room temperature. The reaction mixture was washed sequentially with water, 5percent aqueous NaHCO3, and brine. The organic phase was separated, <n="147"/>dried over MgSO4, filtered and concentrated in vacuo to provide compound 16A, which was used without further purification (0.37 g, 45percent).
35.4% for 3 h; Reflux Compound 2 was prepared according to a similar previously described protocol.
42
To the solution of 4-carboxybenzaldehyde (521 mg, 3.45 mmol) in benzene (6.5 mL) N,N-dimethylformamide di-tert-butyl acetal (2.5 eq, 1760 mg) was added dropwise over a period of 1 h and refluxed.
After 2 h the mixture was cooled down to room temperature and water was added (10 mL).
The organic layer was collected and concentrated in vacuum.
Product was purified chromatographically (silica gel, eluted with Hexane:EtOAc 6:1, v:v).
Compound 2 was obtained in 35.4percent yield.

Reference: [1] Patent: WO2014/25942, 2014, A1, . Location in patent: Page/Page column 29
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2334 - 2356
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 10, p. 1491 - 1508
[4] Patent: WO2006/61715, 2006, A2, . Location in patent: Page/Page column 37
[5] Patent: WO2008/130584, 2008, A1, . Location in patent: Page/Page column 145-146
[6] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 18, p. 5062 - 5068
[7] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 5818 - 5823
  • 22
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YieldReaction ConditionsOperation in experiment
34% With dmap In tetrahydrofuran EXAMPLE 32
Compound 32-A: 4-Formyl-benzoic acid tert-butyl ester
A suspension of 4-carboxybenzaldehyde (5.2 g, 34.6 mmol) in tetrahydrofuran (130 ml) was treated under argon with di-tert-butyl dicarbonate (15.3 g, 70.0 mmol) and 4-dimethylaminopyridine (1.28 g, 10.0 mmol) and the resulting mixture was stirred at 22° C. for 72 h.
After dilution with dichloromethane, the reaction mixture was washed successively with 5percent citric acid, saturated sodium bicarbonate and brine and dried over anhydrous magnesium sulphate.
Evaporation of the solvent under reduced pressure and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 95:5) yielded 2.43 g (34percent yield) of the title ester as a white solid. 1H-NMR 400 MHz (CDCl3) δ (ppm): 1.61 (9H, s, t-Bu), 7.92 (2H, d, J=8.3 Hz, aromatics), 8.13 (2H, d, J=8.3 Hz, aromatics), 10.09 (1H, s, CH).
28% With dmap In tetrahydrofuran at 20℃; for 16 h; Example 1tert-Butyl 4-formylbenzoateTo a 250-mL round-bottom flask was added 4-formylbenzoic acid (5.0 g, 33 mmol), di-tert-butyldicarbonate (14.54 g, 66.6 mmol), N,N-dimethylaminopyridine (0.814 g, 6.66 mmol), and THF (100 mL). The mixture was stirred at rt for 16 h. The solvent was then removed to give a solid. To the residue was added EtOAc (150 mL), sat. NaHCO3 solution (25 mL), and water (25 mL). After separation, the aqueous layer was extracted with EtOAc (2.x.100 mL). The combined organic phases were washed with brine (50 mL), dried (MgSO4), and concentrated. Purification via flash chromatography (hexanes to 10percent EtOAc-hexanes) afforded tert-butyl 4-formylbenzoate (1.90 g, 28percent) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 10.10 (s, 1H), 8.14 (d, J=8.3 Hz, 2H), 7.93 (d, J=8.5 Hz, 2H), 1.61 (s, 9H).
Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2009, vol. 131, p. 7488 - 7489
[3] Patent: US2003/176495, 2003, A1,
[4] Patent: US2011/212969, 2011, A1, . Location in patent: Page/Page column 109
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Reference: [1] Patent: WO2005/97760, 2005, A1, . Location in patent: Page/Page column 65; 17/24
  • 24
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Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1978 - 1982
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Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 21, p. 8357 - 8363
  • 26
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3435 - 3439
  • 27
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  • [ 619-66-9 ]
  • [ 108035-45-6 ]
YieldReaction ConditionsOperation in experiment
83% With hydrogenchloride In ammonium hydroxide; water Step 1:
4-(1H-Imidazol-2-yl)-benzoic Acid (248)
To a stirred solution of 4-formylbenzoic acid (2.00 g, 12.3 mmol) in ammonium hydroxide (9 ml) was added glyoxal (2.86 ml, 20.0 mmol).
The reaction mixture was stirred 16 h at room temperature. 1N HCl was added to the reaction mixture to acidify to pH 5.
The solvent was evaporated and the residue was triturated 30 min. in water (20 ml) and filtered to obtain the title compound 248 (2.08 g, 83percent) as a white solid. LRMS: 188.1 (Calc.); 189.1 (found).
83% With hydrogenchloride In ammonium hydroxide; water Step 1:
4-(1H-Imidazol-2-yl)-benzoic acid (248)
To a stirred solution of 4-formylbenzoic acid (2.00 g, 12.3 mmol) in ammonium hydroxide (9 ml) was added glyoxal (2.86 ml, 20.0 mmol).
The reaction mixture was stirred 16 h at room temperature. 1N HCl was added to the reaction mixture to acidify to pH 5.
The solvent was evaporated and the residue was triturated 30 min. in water (20 ml) and filtered to obtain the title compound 248 (2.08 g, 83percent) as a white solid. LRMS: 188.1 (Calc.); 189.1 (found).
83% With hydrogenchloride In ammonium hydroxide; water Step 1:
4-(1H-Imidazol-2-yl)-benzoic acid (248)
To a stirred solution of 4-formylbenzoic acid (2.00 g, 12.3 mmol) in ammonium hydroxide (9 ml) was added glyoxal (2.86 ml, 20.0 mmol).
The reaction mixture was stirred 16 h at room temperature. 1N HCl was added to the reaction mixture to acidify to pH 5.
The solvent was evaporated and the residue was triturated 30 min. in water (20 ml) and filtered to obtain the title compound 248 (2.08 g, 83percent) as a white solid. LRMS: 188.1 (Calc.).
189.1 (found).
Reference: [1] Patent: US2004/142953, 2004, A1,
[2] Patent: US2005/288282, 2005, A1,
[3] Patent: US6897220, 2005, B2,
[4] Journal of Medicinal Chemistry, 1987, vol. 30, # 8, p. 1342 - 1347
[5] Patent: US2003/119811, 2003, A1,
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Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1978 - 1982
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 10, p. 1491 - 1508
  • 29
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  • [ 73183-34-3 ]
  • [ 128376-64-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 51, p. 16721 - 16726[2] Angew. Chem., 2018, vol. 130, p. 16963 - 16968,6
  • 30
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  • [ 90035-34-0 ]
Reference: [1] Patent: EP1216225, 2005, B1, . Location in patent: Page/Page column 43
  • 31
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  • [ 106261-48-7 ]
YieldReaction ConditionsOperation in experiment
90% With sodium tetrahydroborate; acetic acid In chloroform at 0 - 20℃; for 13 h; General procedure: AcOH (100percent) (140 mL, 2.44 ml) was added over 1 h to a flask containing stirred NaBH4 (20.0 g, 0.53 ml) and CHCl3 (220 mL) at 0-5 °. The resulting mixture was stirred at 0-5 ° for 1.5 h and 1-methylpiperazine (1) (28.0 ml, 0.25 ml) and a solution of methyl 4-formylbenzoate (2a) (43.4 g, 0.26 ml) in CHCl3 (60 mL) were added. The resulting mixture was stirred at 0-5 ° for 1 h and then for 12 h at rt. the mixture was treated with H2O (150 mL) and Na2CO3 until pH 8.0-9.0. The aqueous phase was extracted with EtOAc (2 .x. 100 ml) then both organic layers were combined, washed with H2O (1 .x. 100 ml), and dried over anhydrous Na2SO4. Filtration and evaporation of the solvents gave methyl 4-[(4-methylpiperazin-1-yl)methyl]benzoate (4a): yellowish oil; yield: 61.6 g, 99percent.
70% With platinum on carbon; hydrogen In methanol at 80℃; for 20 h; A suspension of 4-formylbenzoic acid (10.0 g, 67 mmol) in methanol (100 ml) is treated sequentially with 1-methylpiperazine (7.3 g, 73 mmol) and platinum (5percent) on sulfided carbon (1 g). The resulting suspension is then heated at 80° C. and is subjected to a pressure of 5 bar of hydrogen for a period of 20 hrs until the hydrogen uptake is complete. The reaction mixture is cooled to room temperature and filtrated over a pad of Celite. Water (20 ml) is used to rinse the reactor and dissolve the fraction of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid that crystallizes on the walls during the cooling of the reaction mixture. The resulting aqueous solution is filtrated over the pad of Celite employed previously. The combined filtrates are concentrated in vacuo and crystallized in EtOH/H2O 9:1 v/v to give 10.9 g (70percent) of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid as colorless crystals.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5056 - 5058
[2] Russian Journal of Organic Chemistry, 2013, vol. 49, # 4, p. 563 - 567[3] Zh. Org. Khim., 2013, vol. 49, # 4, p. 580 - 584
[4] Patent: US9573928, 2017, B2, . Location in patent: Page/Page column 13-14
[5] Russian Journal of Organic Chemistry, 2011, vol. 47, # 10, p. 1556 - 1563
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  • [ 106261-48-7 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2007, vol. 43, # 12, p. 1540 - 1543
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  • [ 158014-74-5 ]
Reference: [1] Inorganic Chemistry, 2017, vol. 56, # 22, p. 13679 - 13696
[2] European Journal of Inorganic Chemistry, 2010, # 19, p. 3040 - 3050
[3] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19189 - 19198
[4] Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 340, p. 170 - 180
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YieldReaction ConditionsOperation in experiment
67% for 2 h; Reflux Example 2Compound 5: CFTRinh-172; Synthesis of CFTRinh-172 (4-[[4-Oxo-2-thioxo-3-[3-(trifluoromethyl)phenyl]-5-thiazolidinylidene]methyl]benzoic acid) was performed as described in Example 1. See Scheme 1.A mixture of 2-thioxo-3-(3-trifluoromethyl phenyl)-4-thiazolidinone (prepared as described above for intermediate 3) (55 mg, 0.2 mmol), 4-carboxybenzaldehyde (30 mg, 0.2 mmol), and a drop of piperidine in absolute ethanol (0.5 ml) was refluxed for 2 h. Solvent was evaporated, and the residue was crystallized from ethanol and further purified by normal phase flash chromatography to yield 54 mg yellow powder (yield 67percent); mp 180-182° C.; 1H NMR (DMSO-d6): δ 13.20 (bs, 1H, COOH, D2O exchange), 8.07 (d, 2H, carboxyphenyl, J=8.31 Hz), 7.80-8.00 (m, 5H, trifluoromethyl-phenyl and CH), 7.78 (d, 2H, carboxyphenyl, J=8.2 Hz); MS (ES-) (m/z): [M-1]- calculated for C18H9F3NO3S2, 408.40. found 408.23.
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 8187 - 8195
[2] Patent: US2011/105565, 2011, A1, . Location in patent: Page/Page column 28
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  • [ 619-66-9 ]
  • [ 86620-81-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3754 - 3760
  • 36
  • [ 619-66-9 ]
  • [ 1073612-91-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 8187 - 8195
  • 37
  • [ 619-66-9 ]
  • [ 1134776-39-8 ]
Reference: [1] Patent: US2011/212969, 2011, A1,
  • 38
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  • [ 895519-97-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3754 - 3760
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