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Organic Building Blocks
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Aniline
5-Amino-2-methoxybenzoic acid
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fluorobenzene 4-methoxyphenyl benzoic acid benzoyl benzyl p-anisyl

[ CAS No. 3403-47-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 3403-47-2
Chemical Structure| 3403-47-2
Chemical Structure| 3403-47-2
Structure of 3403-47-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 3403-47-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3403-47-2 ]

SDS Specification
Alternatived Products of [ 3403-47-2 ]

Product Details of [ 3403-47-2 ]

CAS No. :3403-47-2 MDL No. :MFCD09260887
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :LWWPSEIFAKNPKQ-UHFFFAOYSA-N
M.W : 167.16 Pubchem ID :13549244
Synonyms :

Calculated chemistry of [ 3403-47-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.3
TPSA : 72.55 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) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.91
Log Po/w (XLOGP3) : 0.45
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : -0.37
Log Po/w (SILICOS-IT) : 0.5
Consensus Log Po/w : 0.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -1.4
Solubility : 6.69 mg/ml ; 0.04 mol/l
Class : Very soluble
Log S (Ali) : -1.54
Solubility : 4.8 mg/ml ; 0.0287 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.53
Solubility : 4.91 mg/ml ; 0.0294 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 3403-47-2 ]

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 [ 3403-47-2 ]

* 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.

  • Downstream synthetic route of [ 3403-47-2 ]

[ 3403-47-2 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 40751-89-1 ]
  • [ 3403-47-2 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; The product from the hydrolysis was dissolved 120 mL of MeOH-THF (5:1), and Pd-C (10% wt. 1.7 g 94.7 mmol) was introduced. The resulting mixture was charged hydrogen by a balloon, and stirred at room temperature overnight. The catalyst was filtered with celite and solvent was removed under reduced pressure. The product was dried under vacuum overnight. Yield: 8.3 g, 100%.
Reference： [1]Patent: US9155738,2015,B2 .Location in patent: Page/Page column 377
[2]European Journal of Organic Chemistry,2020
[3]Justus Liebigs Annalen der Chemie,1922,vol. 429,p. 164
[4]Journal of the Chemical Society,1917,vol. 111,p. 232
[5]Patent: DE71258,
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 3,p. 838
  • 2
  • [ 3403-47-2 ]
  • [ 190248-42-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-6-methoxy-benzoic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0℃; for 0.25h;
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 3
  • [ 3403-47-2 ]
  • [ 108-24-7 ]
  • [ 191605-08-0 ]
YieldReaction ConditionsOperation in experiment
80% With dmap In tetrahydrofuran at 20℃; for 1h;
Reference： [1]Zhu, Jiang; Lin, Jian-Bin; Xu, Yun-Xiang; Jiang, Xi-Kui; Li, Zhan-Ting [Tetrahedron, 2006, vol. 62, # 51, p. 11933 - 11941]
  • 4
  • [ 3403-47-2 ]
  • [ 111-36-4 ]
  • [ 917484-08-3 ]
YieldReaction ConditionsOperation in experiment
70% In tetrahydrofuran at 20℃; for 24h;
Reference： [1]Zhu, Jiang; Lin, Jian-Bin; Xu, Yun-Xiang; Jiang, Xi-Kui; Li, Zhan-Ting [Tetrahedron, 2006, vol. 62, # 51, p. 11933 - 11941]
  • 5
  • [ 3403-47-2 ]
  • 5-(3-butyl-ureido)-2-methoxy-benzoic acid pentafluorophenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 70 percent / tetrahydrofuran / 24 h / 20 °C 2: 4-(dimethylamino)pyridine; DCC / CHCl3 / 1 h / 20 °C
Reference： [1]Zhu, Jiang; Lin, Jian-Bin; Xu, Yun-Xiang; Jiang, Xi-Kui; Li, Zhan-Ting [Tetrahedron, 2006, vol. 62, # 51, p. 11933 - 11941]
  • 6
  • [ 3403-47-2 ]
  • 5-(3-Butyl-ureido)-N-[2,4-dimethoxy-5-(2-methoxy-benzoylamino)-phenyl]-2-methoxy-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 70 percent / tetrahydrofuran / 24 h / 20 °C 2: 4-(dimethylamino)pyridine; DCC / CHCl3 / 1 h / 20 °C 3: 70 percent / HOBt / CHCl3 / 24 h / Heating
Reference： [1]Zhu, Jiang; Lin, Jian-Bin; Xu, Yun-Xiang; Jiang, Xi-Kui; Li, Zhan-Ting [Tetrahedron, 2006, vol. 62, # 51, p. 11933 - 11941]
  • 7
  • [ 3403-47-2 ]
  • <i>N</i>,<i>N</i>'-bis-[5-(5-acetylamino-2-methoxy-benzoylamino)-2,4-dibutoxy-phenyl]-2-methoxy-isophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 1 h / 20 °C 2: 68 percent / HATU; DIEA / dimethylformamide / 12 h / 20 °C
Reference： [1]Zhu, Jiang; Lin, Jian-Bin; Xu, Yun-Xiang; Jiang, Xi-Kui; Li, Zhan-Ting [Tetrahedron, 2006, vol. 62, # 51, p. 11933 - 11941]
  • 8
  • [ 3403-47-2 ]
  • 2-(3-azidomethyl-4-methoxy-phenyl)-5-methyl-2<i>H</i>-pyrazole-3-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C 4.1: 0.9 g / NaBH4 / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 5.1: 0.72 g / Et3N / CHCl3 / 18 h / 0 - 20 °C 6.1: NaN3 / dimethylformamide / 6 h / 60 °C 7.1: 0.17 g / aq. NaOH / ethanol / 4 h / 45 °C 8.1: oxalyl chloride; DMF / CH2Cl2; CHCl3 / 3 h / 0 - 20 °C
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 9
  • [ 3403-47-2 ]
  • [ 637318-35-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C 4.1: 0.9 g / NaBH4 / tetrahydrofuran; H2O / 4 h / 0 - 20 °C
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 10
  • [ 3403-47-2 ]
  • [ 637318-33-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C 4.1: 0.9 g / NaBH4 / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 5.1: 0.72 g / Et3N / CHCl3 / 18 h / 0 - 20 °C 6.1: NaN3 / dimethylformamide / 6 h / 60 °C 7.1: 0.17 g / aq. NaOH / ethanol / 4 h / 45 °C
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 11
  • [ 3403-47-2 ]
  • [ 637318-31-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 12
  • [ 3403-47-2 ]
  • [ 637318-39-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C 4.1: 0.9 g / NaBH4 / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 5.1: 0.72 g / Et3N / CHCl3 / 18 h / 0 - 20 °C 6.1: NaN3 / dimethylformamide / 6 h / 60 °C
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 13
  • [ 3403-47-2 ]
  • [ 637318-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C 4.1: 0.9 g / NaBH4 / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 5.1: 0.72 g / Et3N / CHCl3 / 18 h / 0 - 20 °C
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 14
  • [ 3403-47-2 ]
  • 2-(3-isobutoxycarbonyloxycarbonyl-4-methoxy-phenyl)-5-methyl-2<i>H</i>-pyrazole-3-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 15
  • [ 3403-47-2 ]
  • [ 637318-41-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C 4.1: 0.9 g / NaBH4 / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 5.1: 0.72 g / Et3N / CHCl3 / 18 h / 0 - 20 °C 6.1: NaN3 / dimethylformamide / 6 h / 60 °C 7.1: 0.17 g / aq. NaOH / ethanol / 4 h / 45 °C 8.1: oxalyl chloride; DMF / CH2Cl2; CHCl3 / 3 h / 0 - 20 °C 9.1: 1.4 g / Et3N; DMAP / CHCl3 / 18 h / 0 - 20 °C
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 16
  • [ 3403-47-2 ]
  • [ 637318-46-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C 4.1: 0.9 g / NaBH4 / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 5.1: 0.72 g / Et3N / CHCl3 / 18 h / 0 - 20 °C 6.1: NaN3 / dimethylformamide / 6 h / 60 °C 7.1: 0.17 g / aq. NaOH / ethanol / 4 h / 45 °C 8.1: oxalyl chloride; DMF / CH2Cl2; CHCl3 / 3 h / 0 - 20 °C 9.1: 1.4 g / Et3N; DMAP / CHCl3 / 18 h / 0 - 20 °C 10.1: SnCl2*2H2O / methanol / 18 h / 20 °C
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 17
  • [ 3403-47-2 ]
  • 1-(3-aminomethyl-4-methoxyphenyl)-3-methyl-1H-pyrazole-5-(N-(2'-aminosulfonyl-[1,1']-biphen-4-yl))carboxamide, trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: SnCl2*2H2O; HCl / H2O / 0.25 h / 0 °C 2.1: acetonitrile; H2O / 3 h / Heating 3.1: N-methylmorpholine / tetrahydrofuran / 0.33 h / 0 °C 4.1: 0.9 g / NaBH4 / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 5.1: 0.72 g / Et3N / CHCl3 / 18 h / 0 - 20 °C 6.1: NaN3 / dimethylformamide / 6 h / 60 °C 7.1: 0.17 g / aq. NaOH / ethanol / 4 h / 45 °C 8.1: oxalyl chloride; DMF / CH2Cl2; CHCl3 / 3 h / 0 - 20 °C 9.1: 1.4 g / Et3N; DMAP / CHCl3 / 18 h / 0 - 20 °C 10.1: SnCl2*2H2O / methanol / 18 h / 20 °C 11.1: 73 mg / 1 h / Heating
Reference： [1]Pruitt, James R.; Pinto, Donald J. P.; Galemmo Jr., Robert A.; Alexander, Richard S.; Rossi, Karen A.; Wells, Brian L.; Drummond, Spencer; Bostrom, Lori L.; Burdick, Debra; Bruckner, Robert; Chen, Haiying; Smallwood, Angela; Wong, Pancras C.; Wright, Matthew R.; Bai, Steven; Luettgen, Joseph M.; Knabb, Robert M.; Lam, Patrick Y. S.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5298 - 5315]
  • 18
  • [ 34404-36-9 ]
  • [ 3403-47-2 ]
  • [ 1294448-58-0 ]
YieldReaction ConditionsOperation in experiment
65% In ethyl acetate; for 24h;Reflux; Step 1: Preparation of Compound 2-3A mixture of compound 2-1 (0.477 g, 1.00 mmol) and compound 2-2 (0.200 g, 1.20 mmol) in ethyl acetate (5.0 mL) was stirred vigorously while heating to a gentle reflux. The reaction mixture, initially a suspension, became a solution but over time some solid deposited on the reaction flask wall. After 24 hours the reaction was found to be complete by HPLC analysis. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and serially extracted with distilled water until the resultant aqueous wash had a neutral pH. The organic fraction was dried over Na2SO4, filtered, and concentrated to provide 0.552 g (greater than theoretical yield due to trapped solvent) of viscous orange syrup that MS/HPLC analysis showed to be 99% compound 2-3. This crude material was purified by crystallization from ethyl acetate to obtain a first crop of 0.345 g (65%) of compound 2-3 as a white powder that had a purity of >99% by MS/HPLC analysis.
Reference： [1]Patent: US2011/98498,2011,A1 .Location in patent: Page/Page column 34; 37
  • 19
  • [ 21160-83-8 ]
  • [ 3403-47-2 ]
  • [ 1294448-76-2 ]
YieldReaction ConditionsOperation in experiment
57% In ethyl acetate; for 67.0h;Reflux; Step 6: Preparation of Compound 2-10A mixture of compound 2-9 (0.064 g, 0.125 mmol) and 2-2 (0.025 g, 0.15 mmol) in ethyl acetate (5.0 mL) was stirred vigorously while heating to a gentle reflux. The reaction mixture was a suspension with very fine particles. The reaction progress was monitored by MS/HPLC and found to be complete after 67 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and serially extracted with distilled water until the resultant aqueous wash had a neutral pH. The organic fraction was dried over Na2SO4, filtered, and concentrated to obtain 0.065 g (92%) of beige waxy residue that MS/HPLC analysis showed to be 89% compound 2-10. This crude material was purified by crystallization from ethyl acetate. Obtained a first crop of 0.040 g (57%) of compound 2-10 as a white powder that had a purity of >99% by MS/HPLC analysis.
Reference： [1]Patent: US2011/98498,2011,A1 .Location in patent: Page/Page column 35; 38
  • 20
  • [ 3403-47-2 ]
  • [ 1294448-60-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethyl acetate / 24 h / Reflux 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / chloroform / 20 - 25 °C / Industry scale
Reference： [1]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US2011/98498, 2011, A1
  • 21
  • [ 3403-47-2 ]
  • [ 1294448-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ethyl acetate / 24 h / Reflux 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / chloroform / 20 - 25 °C / Industry scale 3.1: water; lithium hydroxide / tetrahydrofuran; methanol / 10 - 20 °C / Industry scale 3.2: Industry scale
Reference： [1]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US2011/98498, 2011, A1
  • 22
  • [ 3403-47-2 ]
  • [ 1294448-62-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ethyl acetate / 24 h / Reflux 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / chloroform / 20 - 25 °C / Industry scale 3.1: water; lithium hydroxide / tetrahydrofuran; methanol / 10 - 20 °C / Industry scale 3.2: Industry scale 4.1: chloroformic acid ethyl ester; N-ethyl-N,N-diisopropylamine / chloroform / 10 - 20 °C / Industry scale 4.2: 0 °C / Industry scale
Multi-step reaction with 2 steps 1: ethyl acetate / 24 h / Reflux 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 40 h / 20 °C
Reference： [1]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US2011/98498, 2011, A1
[2]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US2011/98498, 2011, A1
  • 23
  • [ 3403-47-2 ]
  • [ 1294448-63-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: ethyl acetate / 24 h / Reflux 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / chloroform / 20 - 25 °C / Industry scale 3.1: water; lithium hydroxide / tetrahydrofuran; methanol / 10 - 20 °C / Industry scale 3.2: Industry scale 4.1: chloroformic acid ethyl ester; N-ethyl-N,N-diisopropylamine / chloroform / 10 - 20 °C / Industry scale 4.2: 0 °C / Industry scale 5.1: trifluoroacetic acid / dichloromethane / 1.5 h / 0 - 20 °C
Multi-step reaction with 3 steps 1: ethyl acetate / 24 h / Reflux 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 40 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 1.5 h / 0 - 20 °C
Reference： [1]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US2011/98498, 2011, A1
[2]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US2011/98498, 2011, A1
  • 24
  • [ 6066-82-6 ]
  • [ 3403-47-2 ]
  • [ 407-25-0 ]
  • [ 1337538-61-0 ]
YieldReaction ConditionsOperation in experiment
73% With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
Reference： [1]Location in patent: experimental part Leonard, Nicholas M.; Brunckova, Jarmila [Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9169 - 9174]
  • 25
  • [ 3403-47-2 ]
  • C16H14N2O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.1: 2,4,6-trimethyl-pyridine / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere
Reference： [1]Leonard, Nicholas M.; Brunckova, Jarmila [Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9169 - 9174]
  • 26
  • [ 3403-47-2 ]
  • [ 75164-01-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.1: trifluoroacetic anhydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere 2.3: 0 - 20 °C / Inert atmosphere
Reference： [1]Leonard, Nicholas M.; Brunckova, Jarmila [Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9169 - 9174]
  • 27
  • [ 589-18-4 ]
  • [ 3403-47-2 ]
  • [ 1347032-84-1 ]
YieldReaction ConditionsOperation in experiment
68% With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; sealed tube;
Reference： [1]Hikawa, Hidemasa; Yokoyama, Yuusaku [Organic Letters, 2011, vol. 13, # 24, p. 6512 - 6515]
  • 28
  • [ 3403-47-2 ]
  • [ 100-51-6 ]
  • [ 1347032-81-8 ]
YieldReaction ConditionsOperation in experiment
58% With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; sealed tube;
Reference： [1]Hikawa, Hidemasa; Yokoyama, Yuusaku [Organic Letters, 2011, vol. 13, # 24, p. 6512 - 6515]
  • 29
  • [ 3403-47-2 ]
  • [ 62-53-3 ]
  • [ 1281707-33-2 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 3-amino-6-methoxy-benzoic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20℃; Stage #2: aniline In dichloromethane 4 3-Amino-5-methoxy-N-phenylbenzamide (5-M) 4.2.5.4 5-Amino-2-methoxy-N-phenylbenzamide (6-M) Compound 6-M was synthesised using a method similar to that of 1-M5 and was isolated as a white solid (yield: 61%). Mp: 201-202 °C. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.75 (1H, s, NH), 7.73 (2H, d, J = 6.4 Hz, PhH), 7.44 (1H, d, J = 6.8 Hz, PhH), 7.30 (3H, m, PhH), 7.02 (1H, m, PhH), 6.45 (1H, d, J = 6.8 Hz, PhH), 5.54 (2H, br s, NH2), 3.90 (3H, s, OCH3). ESI-MS (m/z): 243 (M + H)+.
Reference： [1]Hao, Lan-Hu; Li, Yan-Ping; He, Wei-Ying; Wang, Hui-Qiang; Shan, Guang-Zhi; Jiang, Jian-Dong; Li, Yu-Huan; Li, Zhuo-Rong [European Journal of Medicinal Chemistry, 2012, vol. 55, p. 117 - 124]
  • 30
  • [ 6066-82-6 ]
  • [ 3403-47-2 ]
  • [ 1584636-58-7 ]
YieldReaction ConditionsOperation in experiment
26% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h; Darkness;
Reference： [1]Domaille, Dylan W.; Cha, Jennifer N. [Chemical Communications, 2014, vol. 50, # 29, p. 3831 - 3833]
  • 31
  • [ 118-48-9 ]
  • [ 3403-47-2 ]
  • 5-(2-aminobenzamido)-2-methoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% In ethanol for 1h; Reflux;
Reference： [1]Merk, Daniel; Lamers, Christina; Ahmad, Khalil; Carrasco Gomez, Roberto; Schneider, Gisbert; Steinhilber, Dieter; Schubert-Zsilavecz, Manfred [Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8035 - 8055]
  • 32
  • [ 3403-47-2 ]
  • [ 610-14-0 ]
  • C15H12N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 20℃; 4.2.1.2 ortho-Nitrobenzoylation with benzoic acid derivatives (b) General procedure: ortho-Nitrobenzoic acid derivative (10, 1.0equiv) was dissolved in CH2Cl2 (abs, 5mL/mmol 10) and DMF (abs, 0.1mL/mmol 10). Thionyl chloride (1.3equiv) was added slowly at room temperature and the mixture was stirred 4h under reflux. Solvents were evaporated in vacuum and the crude product (11) was dried in ultra-vacuum. Without further purification the crude product (11) was used for reaction with aniline derivatives (8): for this purpose, the aniline derivative (8, 1.3equiv) was dissolved in CH2Cl2 (abs, 5mL/mmol 8) and pyridine (abs, 1mL/mmol 8) and the crude ortho-nitrobenzoyl chloride derivative (11) in CH2Cl2 (abs, 5mL/mmol 8) was added drop wise. The mixture was stirred at room temperature until TLC indicated consumption of starting material (4-12h). The reaction mixture was then poured into an equal volume 10% hydrochloric acid, phases were separated and the aqueous phase was extracted three times with ethyl acetate. Combined organic layers were dried over Na2SO4 and solvent was evaporated in vacuum. Further purification was performed by recrystallization or column chromatography on silica.
Reference： [1]Merk, Daniel; Lamers, Christina; Weber, Julia; Flesch, Daniel; Gabler, Matthias; Proschak, Ewgenij; Schubert-Zsilavecz, Manfred [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 3, p. 499 - 514]
  • 33
  • [ 96-97-9 ]
  • [ 3403-47-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 60 °C 2: lithium hydroxide; water / methanol; acetonitrile / 3 h / 20 °C 3: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
Reference： [1]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US9155738, 2015, B2
  • 34
  • [ 34841-11-7 ]
  • [ 3403-47-2 ]
Reference： [1]Patent: US9155738,2015,B2
  • 35
  • [ 3403-47-2 ]
  • C42H48N6O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium chloride / N,N-dimethyl-formamide / 6 h / 0 °C
Reference： [1]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US9155738, 2015, B2
  • 36
  • [ 3403-47-2 ]
  • C27H38N6O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium chloride / N,N-dimethyl-formamide / 6 h / 0 °C 3: diethylamine / tetrahydrofuran / 6 h / 0 °C
Reference： [1]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US9155738, 2015, B2
  • 37
  • Fmoc-D-Arg(Pbf)-OPf [ No CAS ]
  • [ 3403-47-2 ]
  • C42H47N5O9S [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; 1.12.4 Synthesis of compound 12 Fmoc-D-Arg(Pbf)-Opf (25 g, 30.68 mmol), compound 2 (5.64 g, 33.75 mmol) were dissolved in anhydrous DMF (85 mL). HOAT (30.78 mmol in 61.4 mL of DMF) and DIEA (6.41 ml, 36.82 mmol) were added to the solution at 0° C. under Ar. The solution was warmed up to room temperature and stirred overnight. The solvent was removed on a rotovap. The product was purified by flash column using DCM: MeOH (25:1 to 15:1). Purification was done on a C18 reverse phase flash column as well using AcCN:water. (0917) Yield: 15.4 g, 57%.
Reference： [1]Current Patent Assignee: INNOVATION PHARMACEUTICALS INC - US9155738, 2015, B2 Location in patent: Page/Page column 377
  • 38
  • [ 22065-57-2 ]
  • [ 3403-47-2 ]
  • 5-((2-ethoxy-2-oxo-1-phenylethyl)amino)-2-methoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With C43H37Br2CuN3P2(1+)*ClO4(1-) In methanol at 0 - 20℃; for 3h; Schlenk technique; Inert atmosphere; chemoselective reaction;
Reference： [1]Ramakrishna, Kankanala; Sivasankar, Chinnappan [Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6609 - 6616]
  • 39
  • [ 761450-22-0 ]
  • [ 3403-47-2 ]
  • 5-(3-(6-fluorobenzo[d]thiazol-2-yl)ureido)-2-methoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% In acetonitrile for 20h; Reflux; 1.4. Generalprocedure for the synthesis of 1-aryl-3-(6-(substituted)benzo[d]thiazol-2-yl)ureas (5-50) General procedure: The aromatic amine (1.1 mmol)was added to the suspension of N-(6-(substituted)benzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamide 2(1 mmol) in dry acetonitrile (15 mL) and the reaction was stirred for20 h at reflux conditions. The reaction was cooled to r.t., quenched with1 M HCl (30 mL) and the precipitate was collected by filtration anddried. The crude product was recrystallized from methanol:diethyl ether toyield corresponding 1-aryl-3-(6-(substituted)benzo[d]thiazol-2-yl)ureas (5-50).
Reference： [1]Hroch, Lukas; Benek, Ondrej; Guest, Patrick; Aitken, Laura; Soukup, Ondrej; Janockova, Jana; Musil, Karel; Dohnal, Vlastimil; Dolezal, Rafael; Kuca, Kamil; Smith, Terry K; Gunn-Moore, Frank; Musilek, Kamil [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3675 - 3678]
  • 40
  • [ 1353531-00-6 ]
  • [ 3403-47-2 ]
  • 5-(3-(6-Chlorobenzo[d]thiazol-2-yl)ureido)-2-methoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% In acetonitrile for 20h; Reflux; 1.4. Generalprocedure for the synthesis of 1-aryl-3-(6-(substituted)benzo[d]thiazol-2-yl)ureas (5-50) General procedure: The aromatic amine (1.1 mmol)was added to the suspension of N-(6-(substituted)benzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamide 2(1 mmol) in dry acetonitrile (15 mL) and the reaction was stirred for20 h at reflux conditions. The reaction was cooled to r.t., quenched with1 M HCl (30 mL) and the precipitate was collected by filtration anddried. The crude product was recrystallized from methanol:diethyl ether toyield corresponding 1-aryl-3-(6-(substituted)benzo[d]thiazol-2-yl)ureas (5-50).
Reference： [1]Hroch, Lukas; Benek, Ondrej; Guest, Patrick; Aitken, Laura; Soukup, Ondrej; Janockova, Jana; Musil, Karel; Dohnal, Vlastimil; Dolezal, Rafael; Kuca, Kamil; Smith, Terry K; Gunn-Moore, Frank; Musilek, Kamil [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3675 - 3678]
  • 41
  • C12H7F3N4O2S [ No CAS ]
  • [ 3403-47-2 ]
  • 2-methoxy-5-(3-(6-(trifluoromethoxy)benzo[d]thiazol-2-yl)ureido)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In acetonitrile for 20h; Reflux; 1.4. Generalprocedure for the synthesis of 1-aryl-3-(6-(substituted)benzo[d]thiazol-2-yl)ureas (5-50) General procedure: The aromatic amine (1.1 mmol)was added to the suspension of N-(6-(substituted)benzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamide 2(1 mmol) in dry acetonitrile (15 mL) and the reaction was stirred for20 h at reflux conditions. The reaction was cooled to r.t., quenched with1 M HCl (30 mL) and the precipitate was collected by filtration anddried. The crude product was recrystallized from methanol:diethyl ether toyield corresponding 1-aryl-3-(6-(substituted)benzo[d]thiazol-2-yl)ureas (5-50).
Reference： [1]Hroch, Lukas; Benek, Ondrej; Guest, Patrick; Aitken, Laura; Soukup, Ondrej; Janockova, Jana; Musil, Karel; Dohnal, Vlastimil; Dolezal, Rafael; Kuca, Kamil; Smith, Terry K; Gunn-Moore, Frank; Musilek, Kamil [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3675 - 3678]
  • 42
  • [ 67-56-1 ]
  • [ 3403-47-2 ]
  • [ 22802-67-1 ]
YieldReaction ConditionsOperation in experiment
88% With sulfuric acid;Reflux; 10.0 g (59.8 mmol, 1.0 equiv.) of 5-amino-2-methoxybenzoic acid were provided in 200 mL of methanol. 9.6 mL (179 mmol, 3.0 equiv.) of sulfuric acid were added dropwise and the reaction mixture was stirred at the reflux temperature over night. After cooling to room temperature and concentration, the remaining material was treated with ethyl acetate and neutralized by addition of a saturated, aqueous solution of sodium bicarbonate. The organic phase was separated, washed withwater, dried over sodium sulfate, filtered and concentrated. 9.54 g (88% of theory) of the title compound were obtained and used without further purification.‘H-NMR (400 MHz, DMSO-d6) 6 [ppm]: 3.309 (13.62), 3.740 (16.00), 4.856 (2.61), 6.715 (1.14), 6.722 (1.20), 6.737 (1.50), 6.744 (1.74), 6.839 (2.69), 6.861 (1.88), 6.885 (2.67), 6.892 (2.49).LC-MS (Method 1): R = 0.47 mm; MS (ESIpos): m/z = 182 [M+H]
Reference： [1]Patent: WO2016/131794,2016,A1 .Location in patent: Page/Page column 47
  • 43
  • [ 3403-47-2 ]
  • N-[4-methoxy-3-(pyridin-4-ylcarbamoyl)phenyl]biphenyl-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfuric acid / Reflux 2: potassium carbonate / acetonitrile / 0 - 20 °C 3: lithium hydroxide; water / 1,4-dioxane / 19 h / 20 °C 4: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 6 h / 20 - 55 °C 5: triethylamine / tetrahydrofuran / 20 °C
Reference： [1]Current Patent Assignee: BAYER AG - WO2016/131794, 2016, A1
  • 44
  • [ 3403-47-2 ]
  • N-{4-methoxy-3-[(3-methoxypropyl)carbamoyl]phenyl}biphenyl-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfuric acid / Reflux 2: potassium carbonate / acetonitrile / 0 - 20 °C 3: lithium hydroxide; water / 1,4-dioxane / 19 h / 20 °C 4: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 6 h / 20 - 55 °C 5: triethylamine / tetrahydrofuran / 20 °C
Reference： [1]Current Patent Assignee: BAYER AG - WO2016/131794, 2016, A1
  • 45
  • [ 3403-47-2 ]
  • methyl 5-[(biphenyl-4-ylcarbonyl)amino]-2-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: potassium carbonate / acetonitrile / 0 - 20 °C
Reference： [1]Current Patent Assignee: BAYER AG - WO2016/131794, 2016, A1
  • 46
  • [ 3403-47-2 ]
  • N-{4-methoxy-3-[(2-methylpyridin-4-yl)carbamoyl]phenyl}biphenyl-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfuric acid / Reflux 2: potassium carbonate / acetonitrile / 0 - 20 °C 3: lithium hydroxide; water / 1,4-dioxane / 19 h / 20 °C 4: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 6 h / 20 - 55 °C 5: triethylamine / tetrahydrofuran / 20 °C
Reference： [1]Current Patent Assignee: BAYER AG - WO2016/131794, 2016, A1
  • 47
  • [ 3403-47-2 ]
  • [ 123-30-8 ]
YieldReaction ConditionsOperation in experiment
79% With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N,N,N,-tetramethylethylenediamine; iron at 170℃; for 24h; Inert atmosphere; regioselective reaction; Phenol by O-Demethyl-Decarboxylation of 2-Methoxybenzoic Acid; Typical Procedure General procedure: Under a nitrogen atmosphere, a mixture of 2-methoxybenzoic acid (761 mg, 5 mmol), metallic iron powder (56 mg, 1 mmol, 0.2 equiv), TMEDA (696 mg, 6 mmol, 1.2 equiv), and DMPU (2.5 mL) was stirredat 170 °C for 24 h. The reaction mixture was cooled to r.t., diluted with 1 N aq HCl (30 mL), and filtered through Celite. The aqueous phase was then extracted with EtOAc (3 × 50 mL) and the combined organic phases were washed with brine (50 mL) and dried overMgSO4. EtOAc was removed in vacuo and the resulting crude material was purified by chromatography (silica gel, CH2Cl2/EtOAc/Et3N,20:1:1) to afford pure phenol as a white solid.
Reference： [1]Cahiez, Gérard; Moyeux, Alban; Zhou, Edouard; Poizat, Maël [Synthesis, 2018, vol. 50, # 10, p. 2119 - 2123]
  • 48
  • C15H11N3O7S3(2-)*2Na(1+) [ No CAS ]
  • [ 3403-47-2 ]
  • C23H17N5O10S3(2-)*2Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; sodium nitrite In water; N,N-dimethyl-formamide at -20 - 25℃; for 2h; 12.2 2. Synthesis of Formazan Compound 12 1.4 g of hydrazone compound 1 was added to a mixed solution of 10 mL of RO water and 5 mL of DMF, and thereby a hydrazone compound 1 solution was produced. 0.334 g of 5-amino-2-methoxybenzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to 1 mL of RO water and 5 mL of DMF to dissolve the compound. This solution was maintained at 0° C., and 400 μL of 9.6 N HCl was added thereto. Subsequently, a sodium nitrite solution (0.152 g dissolved in 1 mL; Wako Pure Chemical Industries, Ltd.) was further added thereto, and diazotization was performed. This diazotized solution was maintained at -20° C., and this solution was added to a hydrazone compound 1 solution. Subsequently, 600 μL of 10 N NaOH was added thereto, subsequently the mixture was stirred at room temperature for 2 hours, and thereby, a solution including formazan compound 12 (formazan compound 12 solution) was produced. The pH of the formazan compound 12 solution was adjusted to neutrality with 9.6 N HCl, the solvent was removed, and thereby formazan compound 12 was obtained.
Reference： [1]Current Patent Assignee: TERUMO CORPORATION - US2019/185465, 2019, A1 Location in patent: Paragraph 0200; 0201
  • 49
  • [ 3403-47-2 ]
  • [ 35265-86-2 ]
  • C15H14N4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In 1,4-dioxane; isopropyl alcohol at 160℃; for 1h; Microwave irradiation; General procedure D General procedure: To a microwave vial was added compound 26a-d (0.3 mmol), appropriate aminobenzoic acid (0.30 mmol), HCl 4M in dioxane (75 μL, 0.30 mmol), and anhydrous isopropanol (6.0 mL). The reaction mixture was heated with stirring in a microwave reactor at 160 °C for 1 hour. And then, the reaction mixture was cooled to room temperature. The precipitate obtained was filtered and washed twice with iPrOH 10 mL each. The residue was dried under high vacuum and used in the later reaction without additional processing. The crude compound (33 mg, 0.1 mmol) obtained previously and benzylamine (11 μL, 0.10 mmol), and anhydrous DMF (0.50 mL) was added to the microwave tube. To a solution was added DMAP (1.2 mg, 0.010 mmol) followed by EDC·HCl (58 mg, 0.30 mmol). The reaction mixture was stirred under N2 balloon at room temperature for 16 hours. And then, the reaction mixture was filtered using Celite. The crude mixture was evaporated and purified using MPLC to obtain 16-17, 19, 22-24.
Reference： [1]Choi, Changyu; Park, Jiwon; Jang, Soyeon; Kim, Jihyung; Lee, Sohee; Min, Kyung Hoon [Bulletin of the Korean Chemical Society, 2022, vol. 43, # 2, p. 232 - 235]
  • 50
  • [ 3403-47-2 ]
  • (2-fluoro-5-nitrophenyl)(phenyl)iodonium triflate [ No CAS ]
  • 5-((2-iodo-4-nitrophenyl)(phenyl)amino)-2-methoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With pyridine; magnesium(II) sulfate at 40℃; for 20h; 6.1 General Procedure (GP7) General procedure: Diaryliodonium salt 1 (1.0 equiv) and MgSO4 (3.0 equiv) were added to a flask followed by addition offreshly distilled pyridine (2.5 - 5 ml per mmol diaryliodonium salt). The flask was transferred to apreheated oil bath at 40 °C. While the resulting suspension was vigorously stirred, the recentlydistilled or sublimated aniline 4 (2.0 equiv) was added and the mixture was stirred for 20 hours.During this time the color changed from an initial deep red to dark orange. After the solvent wasremoved in vacuo (this step is not necessary on small scale), the residue was filtered through a plugof silica with P:Et2O as eluent until the orange (in some cases red) product 5 was collected in itsentirety.
Reference： [1]Bulfield, David; Kervefors, Gabriella; Linde, Erika; Olofsson, Berit; Purkait, Nibadita [Chem, 2022, vol. 8, # 3, p. 850 - 865]

Tags: 3403-47-2 synthesis path| 3403-47-2 SDS| 3403-47-2 COA| 3403-47-2 purity| 3403-47-2 application| 3403-47-2 NMR| 3403-47-2 COA| 3403-47-2 structure

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