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[ CAS No. 53600-33-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 53600-33-2
Chemical Structure| 53600-33-2
Chemical Structure| 53600-33-2
Structure of 53600-33-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 53600-33-2 ]

CAS No. :53600-33-2 MDL No. :MFCD01941328
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DYZDIWNRWSNVPT-UHFFFAOYSA-N
M.W : 167.16 Pubchem ID :2735357
Synonyms :

Calculated chemistry of [ 53600-33-2 ]      Expand+

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) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.0
Log Po/w (XLOGP3) : 0.56
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : -0.37
Log Po/w (SILICOS-IT) : 0.5
Consensus Log Po/w : 0.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.47
Solubility : 5.7 mg/ml ; 0.0341 mol/l
Class : Very soluble
Log S (Ali) : -1.66
Solubility : 3.69 mg/ml ; 0.0221 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 : 1.26

Safety of [ 53600-33-2 ]

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 [ 53600-33-2 ]

* 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 [ 53600-33-2 ]
  • Downstream synthetic route of [ 53600-33-2 ]

[ 53600-33-2 ] Synthesis Path-Upstream   1~33

  • 1
  • [ 53600-33-2 ]
  • [ 917-61-3 ]
  • [ 61948-59-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3018 - 3022
  • 2
  • [ 53600-33-2 ]
  • [ 61948-59-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
  • 3
  • [ 53600-33-2 ]
  • [ 61948-86-5 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With sodium isocyanate; acetic acid In water at 35℃; for 0.5 h;
Stage #2: With sodium hydroxide In water
Stage #3: With hydrogenchloride In water
To a suspension of 2-amino-6-methoxybenzoic acid (1.25 g, 7.5 mmol) in a mixture OfH2O (45 mL) and acetic acid ( 0.75 mL) at 35 0C was added a solution of sodium cyanate (1.2 g, 18 mmol) in H2O (5 mL). The reaction mixture was stirred for 0.5 h and then NaOH (13 g, 330 mmol) was added in small portions to provide a precipitate. After cooling to room temperature, the pH of the reaction mixture was adjusted to 7 with concentrated HCl. The resulting precipitate was filtered, washed thoroughly with water and dried in an oven to provide Intermediate 28 as a white solid (1.0 g, 69percent) 1H NMR (400 MHz, (CD3)2SO) 6 ppm 3.80 (s, 3 H), 6.68 - 6.71 (m, 2 H), 7.49 (t, J=8.35 Hz, 1 H), 10.88 (s, 1 H), 10.98 (s, 1 H). EPO <DP n="93"/>
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 48, p. 17605 - 17614
[2] Patent: WO2007/30582, 2007, A2, . Location in patent: Page/Page column 91
[3] Patent: US5688803, 1997, A,
  • 4
  • [ 53600-33-2 ]
  • [ 57-13-6 ]
  • [ 61948-86-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
  • 5
  • [ 32315-10-9 ]
  • [ 53600-33-2 ]
  • [ 37795-77-0 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 11, p. 914 - 919
  • 6
  • [ 53600-33-2 ]
  • [ 29866-54-4 ]
Reference: [1] Patent: WO2009/62289, 2009, A1,
  • 7
  • [ 53600-33-2 ]
  • [ 18362-30-6 ]
Reference: [1] Patent: WO2009/62289, 2009, A1,
  • 8
  • [ 53600-33-2 ]
  • [ 567-62-4 ]
YieldReaction ConditionsOperation in experiment
75% With boron tribromide In dichloromethane at -78 - 20℃; for 18 h; Inert atmosphere To a solution of 2-amino-6-methoxybenzoic acid (1 equiv) in anhydrous CH2Cl2 at -78 °C (dry ice/acetone bath), boron tribromide (1 M in CH2Cl2, 3 equiv) was added dropwise.
The reaction mixture was stirred for 18 h at room temperature under a nitrogen atmosphere.
After addition of EtOH and MeOH the solvents were evaporated to provide a brown solid which was used for the next reaction step without further purification; brown solid, yield: 75percent.
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 76, p. 343 - 351
[2] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6666 - 6671
  • 9
  • [ 53600-33-2 ]
  • [ 31786-45-5 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 13, p. 4445 - 4452
[2] Synthesis, 1994, # 1, p. 73 - 76
  • 10
  • [ 53967-73-0 ]
  • [ 53600-33-2 ]
Reference: [1] Patent: US5599814, 1997, A,
[2] Journal of the Chemical Society, 1932, p. 1792,1795
[3] Journal of Organic Chemistry, 1941, vol. 6, p. 216,218
  • 11
  • [ 1591-37-3 ]
  • [ 53600-33-2 ]
Reference: [1] Chemische Berichte, 1961, vol. 94, p. 2295 - 2305
[2] Journal of the American Chemical Society, 1977, vol. 99, p. 3734 - 3744
  • 12
  • [ 606-20-2 ]
  • [ 53600-33-2 ]
Reference: [1] Australian Journal of Chemistry, 1980, vol. 33, # 12, p. 2777 - 2779
  • 13
  • [ 603-12-3 ]
  • [ 53600-33-2 ]
Reference: [1] Australian Journal of Chemistry, 1980, vol. 33, # 12, p. 2777 - 2779
  • 14
  • [ 42087-82-1 ]
  • [ 53600-33-2 ]
Reference: [1] Australian Journal of Chemistry, 1980, vol. 33, # 12, p. 2777 - 2779
  • 15
  • [ 77901-52-1 ]
  • [ 53600-33-2 ]
Reference: [1] Australian Journal of Chemistry, 1980, vol. 33, # 12, p. 2777 - 2779
  • 16
  • [ 38469-85-1 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of the American Chemical Society, 1977, vol. 99, p. 3734 - 3744
  • 17
  • [ 136247-94-4 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6666 - 6671
  • 18
  • [ 60144-52-7 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6666 - 6671
  • 19
  • [ 536-90-3 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6666 - 6671
  • 20
  • [ 146463-87-8 ]
  • [ 53600-33-2 ]
Reference: [1] Synthesis, 1994, # 1, p. 73 - 76
  • 21
  • [ 554-84-7 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of Organic Chemistry, 1941, vol. 6, p. 216,218
  • 22
  • [ 855157-00-5 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of Organic Chemistry, 1941, vol. 6, p. 216,218
  • 23
  • [ 64208-72-6 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of Organic Chemistry, 1941, vol. 6, p. 216,218
  • 24
  • [ 154351-20-9 ]
  • [ 53600-33-2 ]
Reference: [1] Synthesis, 1994, # 1, p. 73 - 76
  • 25
  • [ 50868-77-4 ]
  • [ 53600-33-2 ]
Reference: [1] Chemicke Listy, 1954, vol. 48, p. 427,430,431[2] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 966,967,968[3] Chem.Abstr., 1955, p. 3880
[4] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 966,972[5] Chem.Abstr., 1955, p. 3880
  • 26
  • [ 54166-96-0 ]
  • [ 53600-33-2 ]
Reference: [1] Australian Journal of Chemistry, 1980, vol. 33, # 12, p. 2777 - 2779
  • 27
  • [ 340774-74-5 ]
  • [ 53600-33-2 ]
Reference: [1] Chemicke Listy, 1954, vol. 48, p. 427,430,431[2] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 966,967,968[3] Chem.Abstr., 1955, p. 3880
[4] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 966,972[5] Chem.Abstr., 1955, p. 3880
  • 28
  • [ 37439-79-5 ]
  • [ 53600-33-2 ]
Reference: [1] Chemicke Listy, 1954, vol. 48, p. 427,430,431[2] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 966,967,968[3] Chem.Abstr., 1955, p. 3880
  • 29
  • [ 37439-78-4 ]
  • [ 53600-33-2 ]
Reference: [1] Chemicke Listy, 1954, vol. 48, p. 427,430,431[2] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 966,967,968[3] Chem.Abstr., 1955, p. 3880
  • 30
  • [ 5460-31-1 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of the Chemical Society, 1932, p. 1792,1795
  • 31
  • [ 4837-88-1 ]
  • [ 53600-33-2 ]
Reference: [1] Journal of the Chemical Society, 1932, p. 1792,1795
  • 32
  • [ 53600-33-2 ]
  • [ 219773-96-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 22, p. 4077 - 4080
  • 33
  • [ 53600-33-2 ]
  • [ 254964-60-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088
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