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[ CAS No. 6274-22-2 ] {[proInfo.proName]}

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Chemical Structure| 6274-22-2
Chemical Structure| 6274-22-2
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Product Details of [ 6274-22-2 ]

CAS No. :6274-22-2 MDL No. :MFCD00665792
Formula : C8H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :XAGFYNSCWICYPA-UHFFFAOYSA-N
M.W : 150.18 Pubchem ID :235516
Synonyms :

Calculated chemistry of [ 6274-22-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.84
TPSA : 55.12 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) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 0.44
Log Po/w (WLOGP) : 0.64
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 0.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.32
Solubility : 7.19 mg/ml ; 0.0479 mol/l
Class : Very soluble
Log S (Ali) : -1.17
Solubility : 10.3 mg/ml ; 0.0683 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.41
Solubility : 0.588 mg/ml ; 0.00392 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 6274-22-2 ]

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 [ 6274-22-2 ]

* 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 [ 6274-22-2 ]
  • Downstream synthetic route of [ 6274-22-2 ]

[ 6274-22-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 2585-23-1 ]
  • [ 6274-22-2 ]
YieldReaction ConditionsOperation in experiment
86% With water; ammonium chloride; zinc In tetrahydrofuran; methanol Synthesis of 4-Amino-N-methyl-benzamide
Ammonium chloride (29.6 g, 55.4 mmol) in water (200 mL) and methanol (200 mL) was added to a solution of N-methyl-4-nitro-benzamide (10 g, 55.4 mmol) in THF (160 mL).
Zinc powder (29 g, 44.4 mmol) was added portion wise and the mixture stirred for 15 minutes.
The reaction mixture was filtered over celite, the filtrate was then concentrated and extracted with ethyl acetate.
The organics were washed with brine solution, dried over Na2SO4 and concentrated to afford 7.2 g (86percent) of 4-amino-N-methyl-benzamide. 1H NMR: (DMSO-d6): δ 7.9 (s, 1H), 7.6 (d, 2H), 6.5 (d, 2H), 5.6 (s, 2H), 2.7 (s, 3H).
84% With hydrogen In ethanol at 20℃; for 12 h; (b) Preparation of intermediary compound 4-amino-iV-methylbenzamide:To a solution of 7V-methyl-4-nitrobenzamide (23.0 g, 127.8 mmol) in ethanol (460 rnL) was added palladium on carbon (Pd/C, 10percent, 50percent moistened, 15.0 g). The mixture was hydrogenated under 2.0 atmospheric pressure at room temperature for 12 hours. After completion of the reaction, the reaction mixture was filtered through Celite and thoroughly washed with ethanol. The filtrate was evaporated and the residue washed with diisopropyl ether to give 16.0 g (84 percent yield) of 4-amino-N-methylbenzamide as an off-white solid. 1H-NMR (300 MHz, DMSOd6) δ 7.94 (bs, IH), 7.54 (d, J= 8.7 Hz, 2H), 6.52 (d, J= 8.7 Hz, 2H), 5.57 (s, 2H), 2.72 (d, J= 4.5 Hz, 3H). LC-MS 172.5 (M+Na).
Reference: [1] Patent: US2009/239848, 2009, A1, . Location in patent: Page/Page column 24
[2] Patent: WO2010/133672, 2010, A1, . Location in patent: Page/Page column 30
[3] Journal of Chemical Research, 2006, # 4, p. 223 - 224
[4] Journal of Medicinal Chemistry, 1984, vol. 27, # 6, p. 779 - 782
[5] Journal of the American Chemical Society, 1938, vol. 60, p. 1081
  • 2
  • [ 1719-57-9 ]
  • [ 2835-68-9 ]
  • [ 6274-22-2 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 25, p. 4933 - 4936
  • 3
  • [ 122-04-3 ]
  • [ 6274-22-2 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 1081
  • 4
  • [ 96-31-1 ]
  • [ 150-13-0 ]
  • [ 6274-22-2 ]
Reference: [1] Synlett, 2011, # 11, p. 1597 - 1601
  • 5
  • [ 6274-22-2 ]
  • [ 214360-57-3 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 14 - 24
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