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[ CAS No. 66315-15-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 66315-15-9
Chemical Structure| 66315-15-9
Chemical Structure| 66315-15-9
Structure of 66315-15-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 66315-15-9 ]

CAS No. :66315-15-9 MDL No. :MFCD06208249
Formula : C8H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QZZIBMYRWBVKLM-UHFFFAOYSA-N
M.W :166.18 Pubchem ID :11521144
Synonyms :

Calculated chemistry of [ 66315-15-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 3.0
Molar Refractivity : 47.11
TPSA : 75.35 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) : -6.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.77
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : 0.83
Log Po/w (MLOGP) : -0.37
Log Po/w (SILICOS-IT) : 0.18
Consensus Log Po/w : 0.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.61
Solubility : 4.06 mg/ml ; 0.0244 mol/l
Class : Very soluble
Log S (Ali) : -1.96
Solubility : 1.81 mg/ml ; 0.0109 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.84
Solubility : 2.39 mg/ml ; 0.0144 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 66315-15-9 ]

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 [ 66315-15-9 ]

* 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 [ 66315-15-9 ]
  • Downstream synthetic route of [ 66315-15-9 ]

[ 66315-15-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 64-18-6 ]
  • [ 66315-15-9 ]
  • [ 53484-17-6 ]
YieldReaction ConditionsOperation in experiment
99% at 85℃; for 13 h; Step 3: 1-METHYL-LH-BENZO [d] imidazole-5-carboxylic acid (281) [0437] A solution of the di-amino compound 280 (678mg; 4. LMMOL) (or an o-aminophenol) in 50percent HC02H (or any other carboxylic acid or an ortho-ester) in water (or anhydrous solvent if an ortho- ester is used) was stirred at 85°C for 13h, concentrated, the residue was re-dissolved in water and LYOPHILLIZED to afford the title compound 281 (712mg, 99percent YIELD). 1H NMR: (400.2 MHz, DMSO) 6 (ppm): 12.9 (bs; 1H); 8.80 (s ; 1H) ; 8.26 (d, J= 1.6 Hz; 1H); 7.96 (dd, J= 1. 6,8. 6 Hz; 1H); 7.79 (d, J= 8. 6 Hz; 1H); 3.95 (s, 3H). MS: calc : 176.2 ; found: 177.1 (M+H).
84% at 85℃; To a stirred solution of 3-amino-4-(methylamino)benzoic acid (9 g, 1.0 eq) in 50 mL water, was added 50 mL formic acid and heated at 85 °C overnight. The mixture was cooled, concentrated in vacuo, and dissolved in water. Then 2N HC1 was added to adjust pH to 1~3. The suspension was filtered and washed with water to give the product (9.7 g, 84percent). :H NMR (400 MHz, DMSO- ) δ 9.48 (s, 1H), 8.37 (s, 1H), 8.12 (d, J= 8.8 Hz, 1H), 8.00 (d, J= 8.8 Hz, 1H), 4.06 (s, 3H).
Reference: [1] Patent: WO2005/30704, 2005, A1, . Location in patent: Page/Page column 244-245
[2] Patent: WO2013/97773, 2013, A1, . Location in patent: Paragraph 0293
[3] Patent: WO2004/26829, 2004, A2, . Location in patent: Page/Page column 77
  • 2
  • [ 41263-74-5 ]
  • [ 66315-15-9 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In methanol at 20℃; for 2 h; Step 2.
3-Amino-4-(methylamino)benzoic acid
A mixture of 4-(methylamino)-3-nitrobenzoic acid (9.8 g, 49.96 mmol) and palladium on carbon (1 g) in methanol (200 ml) under an atmosphere of H2(g) was stirred for 2 hours at room temperature and the solids were filtered out.
The filtrate was concentrated in vacuo to afford 3-amino-4-(methylamino)benzoic acid as a white solid (8.2 g, 99percent).
LC/MS (ES, m/z): [M+H]+. 167.1
1H-NMR (300 MHz, DMSO) δ 7.47-7.51 (m, 1H), 7.37 (d, J=2.1 Hz, 1H), 6.53 (d, J=8.4 Hz, 1H), 2.90 (s, 3H)
99% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; To a solution of 4-(methylamino)-3-nitrobenzoic acid (4.9 g, 25 mmol) in MeOH (250 ml) was added Pd/C (10 percent, 250 mg) and the resulting mixture was stirred at room temperature under H2 atmosphere. The catalyst was removed by filtration, and the solvent was evaporated in vacuo to give 3-amino-4-(methylamino)benzoic acid (5) (4.14 g, 99 percent) as a black solid. 1H NMR (DMSO-d6, 500 MHz) δ: 2.73 (3H, s), 6.34 (1H, d, J = 8.5 Hz), 7.11 (1H, d, J = 2.0 Hz), 7.19 (1H, dd, J = 8.5, 2.0 Hz).  
36.5% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 48 h; A mixture of 4-(methylamino)-3-nitrobenzoic acid (29 g, 1.0 eq) and Pd/C (5 g, 10percent) in 300 mL MeOH was stirred at rt under hydrogen for 48 h and filtered. The filtrate was concentrated in vacuo to give the product (9 g, 36.5percent). :H NMR (400 MHz, DMSO- ) δ 7.21 (dd, J= 8.4 Hz, 2.0 Hz, 1H), 7.14 (d, J= 2.0 Hz, 1H), 6.37 (d, J= 8.4 Hz, 1H), 5.28 (brs, 1H), 4.60 (brs, 2H), 2.76 (s, 3H).
Reference: [1] Patent: US2012/277224, 2012, A1, . Location in patent: Page/Page column 41
[2] Tetrahedron Letters, 2017, vol. 58, # 43, p. 4145 - 4148
[3] Patent: WO2013/97773, 2013, A1, . Location in patent: Paragraph 0292
[4] Chem.Abstr., 1978, vol. 89, # 61044,
[5] Patent: WO2004/26829, 2004, A2, . Location in patent: Page/Page column 77
[6] Organic Letters, 2008, vol. 10, # 6, p. 1183 - 1186
[7] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 193 - 204
[8] Journal of the American Chemical Society, 2015, vol. 137, # 22, p. 7197 - 7209
[9] Organic Letters, 2017, vol. 19, # 19, p. 5276 - 5279
[10] Organic Letters, 2018, vol. 20, # 14, p. 4306 - 4309
[11] Chem.Abstr., 1979, vol. 90, # 7597,
[12] Chem.Abstr., vol. 89, # 61044,
  • 3
  • [ 64-17-5 ]
  • [ 41263-74-5 ]
  • [ 66315-15-9 ]
Reference: [1] Patent: US2001/53779, 2001, A1,
  • 4
  • [ 453-71-4 ]
  • [ 66315-15-9 ]
Reference: [1] Patent: US2012/277224, 2012, A1,
[2] Journal of the American Chemical Society, 2015, vol. 137, # 22, p. 7197 - 7209
[3] Tetrahedron Letters, 2017, vol. 58, # 43, p. 4145 - 4148
[4] Organic Letters, 2017, vol. 19, # 19, p. 5276 - 5279
[5] Organic Letters, 2018, vol. 20, # 14, p. 4306 - 4309
  • 5
  • [ 96-99-1 ]
  • [ 66315-15-9 ]
Reference: [1] Patent: WO2013/97773, 2013, A1,
  • 6
  • [ 456-22-4 ]
  • [ 66315-15-9 ]
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 43, p. 4145 - 4148
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