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[ CAS No. 18595-13-6 ] {[proInfo.proName]}

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Chemical Structure| 18595-13-6
Chemical Structure| 18595-13-6
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Product Details of [ 18595-13-6 ]

CAS No. :18595-13-6 MDL No. :MFCD11505989
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HCLLOQLXKCCWLJ-UHFFFAOYSA-N
M.W : 165.19 Pubchem ID :583916
Synonyms :

Calculated chemistry of [ 18595-13-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.09
TPSA : 52.32 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 2.01
Log Po/w (WLOGP) : 1.37
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 1.44
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.707 mg/ml ; 0.00428 mol/l
Class : Soluble
Log S (Ali) : -2.74
Solubility : 0.304 mg/ml ; 0.00184 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.531 mg/ml ; 0.00321 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 18595-13-6 ]

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 [ 18595-13-6 ]

* 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 [ 18595-13-6 ]
  • Downstream synthetic route of [ 18595-13-6 ]

[ 18595-13-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 18595-13-6 ]
  • [ 87-59-2 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 13, p. 2094 - 2108
  • 2
  • [ 18595-13-6 ]
  • [ 99548-56-8 ]
Reference: [1] Chemical Communications, 2005, # 44, p. 5583 - 5585
[2] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5956 - 5968
  • 3
  • [ 61940-22-5 ]
  • [ 18595-13-6 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen In methanol; water at 0 - 25℃; for 1.5 h; A mixture of methyl 2-methyl-6-nitrobenzoate (3.80g, 19.5 mmol) and 10percent palladium-carbon (containing 50percent water) (1.03g) was stirred under a hydrogen atmosphere in methanol (20mL) at 20-25°C for 1.5 hours.
After filtering off palladium-carbon, the solvent was distilled off under reduced pressure to give methyl 2-amino-6-methylbenzoate (3.13g, 97percent).
1H-NMR (CDCl3) δ:2.43(3H,s), 3.88(3H,s), 2.37(3H,s), 6.52(1H,s), 6.54(1H,s), 7.08(1H,t,J=7.9Hz)
Reference: [1] Chemical Communications, 2005, # 44, p. 5583 - 5585
[2] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5956 - 5968
[3] Patent: EP1844768, 2007, A1, . Location in patent: Page/Page column 27
[4] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
[5] Patent: US2002/19414, 2002, A1,
[6] Journal of the American Chemical Society, 2014, vol. 136, # 10, p. 3744 - 3747
  • 4
  • [ 4389-50-8 ]
  • [ 18107-18-1 ]
  • [ 18595-13-6 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 1.5 h; Example 130 Synthesis of (+/-)-Isopropyl 5- [acetyl- (3, 5-bistrifluoromethylbenzyl) amino] -6-methyl- tetrahydrobenzo [b] azepine-1-carboxylate Step 1. Preparation of 2-Amino-6-methyl-benzoic acid methyl ester. Dissolve 2-Amino-6-methyl-benzoic acid (3.00 g, 19.8 mmol) in ethylacetate (100 mL) and ethanol (100 mL) and add (trimethylsilyl) diazomethane (19.8 mL, 39.7 mmol, 2M in hexane) at room temperature and stir the solution for 1 h 30 min. Remove the solvent under reduced pressure to afford the title compound (3.30 g, quantitative). lH NMR (CDC13, 300 MHz) S 2.43 (s, 3H), 3.89 (s, 3H), 5.11 (brs, 2H), 6.52 (m, 2H), 7.08 (t, J = 7.7 Hz, 1H). MS (ES+): 166 (M+H).
16.5 g at 20℃; for 4 h; 2.0 M diethyl ether solution of trimethylsilyldiazomethane was added under ice cooling to a mixture of 15.1 g of 2-amino-6-methylbenzoic acid, 150 mL of ethyl acetate, 150 mL of ethanol. After the mixture was stirred at ambient temperature for 4 hr, the reaction mixture was concentrated under reduced pressure to obtain 16.5 g of methyl 2-amino-6-methyl benzoate. Methyl 2-amino-6-methylbenzoate 1H-NMR (CDCl3) δ: 6.94 (1H, t, J = 8.0 Hz), 6.40-6.38 (2H, m), 4.96 (2H, s), 3.75 (3H, s), 2.29 (3H, s).
Reference: [1] Patent: WO2005/37796, 2005, A1, . Location in patent: Page/Page column 122
[2] Patent: WO2013/162072, 2013, A1, . Location in patent: Page/Page column 547
[3] Patent: EP2927218, 2015, A1, . Location in patent: Paragraph 0811
[4] Patent: EP2940012, 2015, A1, . Location in patent: Paragraph 0785
  • 5
  • [ 4389-50-8 ]
  • [ 67-68-5 ]
  • [ 74-88-4 ]
  • [ 18595-13-6 ]
Reference: [1] Patent: US5236917, 1993, A,
[2] Patent: US5296496, 1994, A,
[3] Patent: US5187173, 1993, A,
[4] Patent: US5512589, 1996, A,
[5] Patent: US5128339, 1992, A,
[6] Patent: US5385923, 1995, A,
  • 6
  • [ 13506-76-8 ]
  • [ 18595-13-6 ]
Reference: [1] Chemical Communications, 2005, # 44, p. 5583 - 5585
[2] Journal of the American Chemical Society, 2014, vol. 136, # 10, p. 3744 - 3747
  • 7
  • [ 476170-47-5 ]
  • [ 18595-13-6 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 13, p. 2094 - 2108
  • 8
  • [ 20877-81-0 ]
  • [ 124-41-4 ]
  • [ 18595-13-6 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 2, p. 563 - 578
  • 9
  • [ 80-11-5 ]
  • [ 4389-50-8 ]
  • [ 18595-13-6 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 1, p. 161 - 173
  • 10
  • [ 186581-53-3 ]
  • [ 4389-50-8 ]
  • [ 18595-13-6 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3386 - 3396
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