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[ CAS No. 63069-49-8 ] {[proInfo.proName]}

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Chemical Structure| 63069-49-8
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Product Details of [ 63069-49-8 ]

CAS No. :63069-49-8 MDL No. :MFCD03428522
Formula : C7H7FN2O Boiling Point : -
Linear Structure Formula :- InChI Key :RHJMYIPLYKQZJM-UHFFFAOYSA-N
M.W : 154.14 Pubchem ID :10241003
Synonyms :

Calculated chemistry of [ 63069-49-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.9
TPSA : 69.11 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) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.05
Log Po/w (XLOGP3) : 0.39
Log Po/w (WLOGP) : 0.93
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 0.68
Consensus Log Po/w : 0.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.38
Solubility : 6.44 mg/ml ; 0.0418 mol/l
Class : Very soluble
Log S (Ali) : -1.41
Solubility : 6.04 mg/ml ; 0.0392 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.89
Solubility : 1.98 mg/ml ; 0.0128 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 63069-49-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 63069-49-8 ]

* 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 [ 63069-49-8 ]
  • Downstream synthetic route of [ 63069-49-8 ]

[ 63069-49-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 67-56-1 ]
  • [ 63069-49-8 ]
  • [ 16499-56-2 ]
YieldReaction ConditionsOperation in experiment
77% at 130℃; for 2 h; Inert atmosphere; Microwave irradiation 2-Amino-5-fluorobenzamide (77 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO) (H2O)](5.4 mg, 0.005 mmol, 1 molpercent),Cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.) And methanol (0.5 ml) were sequentially added to a dried 5 mL microwave reaction tube. Nitrogen gas in the microwave tube was placed in a single-mode pressure microwave synthesizer (Discover CEM,USA). After the reaction mixture was reacted at 130 ° C for 2 hours,Cool to room temperature. Rotary evaporation to remove the solvent,Pure target compound was then obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 77percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0055; 0056; 0057; 0058
  • 2
  • [ 63069-49-8 ]
  • [ 149-73-5 ]
  • [ 16499-56-2 ]
YieldReaction ConditionsOperation in experiment
70% at 170℃; for 2 h; Autoclave This compound was previously reported [25] but we used another method for preparation of thiscompound to improve the yield. In a 10 mL volume stainless steel pressure-resistant vessel were placed(1.54 g, 0.01 mol) of 2-amino-5-fluorobenzamide 2, (1.06 g, 0.01 mol) of trimethoxymethane, and 5 mLof DMF. The reaction was heated at 170°C for 2 h. After the reaction was completed the product wascooled, collected, and crystallized from ethyl alcohol. Yield 70percent; mp: 252–254°C; 1H-NMR (DMSO-d6,300 MHz) δ: 7.67 (d, 1H, J = 8.6 Hz, ArH), 7.85 (d, 1H, J = 9.7 Hz, ArH), 8.12 (s, 1H, ArH), 8.73 (dd, 1H,J = 8.4 Hz and 4.8 Hz, ArH), 11.83(s, 1H, NH), C8H5FN2O (164.04): MS (ESI) m/z 165.04 [M + 1].
Reference: [1] Molecules, 2017, vol. 22, # 2,
  • 3
  • [ 63069-49-8 ]
  • [ 16499-61-9 ]
Reference: [1] Molecules, 2017, vol. 22, # 2,
  • 4
  • [ 446-08-2 ]
  • [ 63069-49-8 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With phosgene In tetrahydrofuran; toluene at 20℃; for 18 h;
Stage #2: With ammonia In tetrahydrofuran; water; toluene at 0 - 20℃; for 1 h;
Intermediate 32; 2-Amino-5-fluorobenzamide A round-bottomed flask was charged with 5-fluororanthranilic acid (3 g, 19.34 mmol) in tetrahydrofuran (64.5 mL) and a 20percent solution of phosgene (11.2 mL, 21.3 mmol) in toluene was added dropwise at room temperature. The mixture was stirred for 18 hr at room temperature, then cooled to 0° C., at which time concentrated ammonium hydroxide (27.9 mL, 193 mmol) was added cautiously. The mixture was then allowed to warm to room temperature and then stirred for 1 hr. The organic phase was diluted with EtOAc, washed with aqueous dipotassium hydrogen phosphate and brine, then dried over sodium sulfate and concentrated to give a white solid (2.46 g, 82percent yield). MS: M(C7H7FN2O)=154.14, (M+H-NH3)-=138.
75%
Stage #1: With thionyl chloride In benzene for 4 h; Reflux
Stage #2: With ammonia In benzene at 20℃;
A suspension of 2-amino-5-fluorobenzoic acid (1) (1.0 g, 6.3 mmol) in benzene (30 mL) underreflux was mixed with thionyl chloride (1.5 g, 12.6 mmol). The resulting mixture was stirred underreflux for 4 h, and then evaporated. The residue was dissolved in 200 mL of benzene and treated with anhydrous ammonia gas at room temperature. After removing the solvent, compound 2 wascrystalized from ethanol and obtained as brown powder [25]. Yield 75percent; m.p.: 144–146°C; 1H-NMR(DMSO-d6, 300 MHz) δ: 5.72(s, 2H, NH2,), 6.54(s, CONH2, 2H) 7.63 (d, 1H, J = 8.6 Hz, Ar-H),7.92 (d, 1H, J = 7.4 Hz, Ar-H), 8.14 (s, 1H, Ar-H). C7H7FN2O (154.05): MS (ESI) m/z 155.05 [M + 1].
67% With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 6 h; To a stirred solution of 2-amino-5-fluoro-benzoic acid (15 g, 96.69 mmol) in THF (300 mL),EDC.HCl (27.70 g, 145.03 mmol), HOBt·NH3 (21.75 g, 145.03 mmol) and DIPEA (51.0 mL,290.07 mmol) were added at RT and stirred for 6 h (TLC indicated complete consumption ofstarting material). The reaction mixture was concentrated under reduced pressure to give thecrude residue which was diluted with water (150 mL) and extracted with EtOAc (3 x 150mL). The combined organic extracts were washed with water (2 x 100 mL), brine (1 x 100mL), dried over Na2S04, and concentrated under reduced pressure to give the crude residue.The crude material was purified by column chromatography (100-200 silica gel, 300 g, 40percentEtOAc-Hexane) to provide 2-amino-5-fluoro-benzamide (10.0 g, 67percent) as a pale yellow solid.LCMS: mlz: 155.38 [M+Ht.
Reference: [1] Patent: US2008/182852, 2008, A1, . Location in patent: Page/Page column 28
[2] Molecules, 2017, vol. 22, # 2,
[3] Patent: WO2018/125961, 2018, A1, . Location in patent: Page/Page column 77
[4] Journal of Medicinal Chemistry, 2000, vol. 43, # 23, p. 4479 - 4487
[5] Patent: US6479499, 2002, B1,
  • 5
  • [ 77206-97-4 ]
  • [ 63069-49-8 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In ethanol for 5 h; To a dry flask purged with N2 was added 10percent Pd/C (483 mg) followed by 5-fluoro-2- nitrobenzamide (Example 14, 4.83 g, 26.2 mmol) as a solution in ethanol (130 mL). The mixture was stirred under an H2 atmosphere for 5 h. The mixture was filtered through a pad of Celite and the solvent was evaporated under reduced pressure to afford 4.03 g (99percent) of the desired product. 1H NMR (300 MHz, DMSO-c/6) δ 7.75 (br s, 1 H), 7.45-7.29 (m, 1 H), 7.18 (br s, 1 H), 7.10-6.93 (m, 1 H), 6.74-6.58 (m,i H), 6.43 (br s, 2H); ES-MS m/z 155.0 [M+Hf, LCMS RT (min) 0.27
82% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2 h; Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of 5-fluoro-2-nitrobenzamide (17.5 g, 95.04 mmol, 1.00 equiv) and palladium carbon (10percent) (1.75 g, 0.10 equiv) in methanol (150 mL). To the above H2 (enough) was introduced. The resulting solution was stirred for 2 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 12.0 g (82percent) of 2- amino-5-fluorobenzamide as a white solid. MS (ESI) m/z 155 ([M + H]+)
0.8 g With palladium 10% on activated carbon; hydrogen In methanol General procedure: (a) Thionyl chloride (1.5 g, 12.6 mmol) was added dropwise to a suspension of a 5-substituted-2-nitrobenzoic acid (1a: 1.1 g, 6.3 mmol; 1b: 1.2 g, 6.3 mmol) in dichloroethane (30 mL) under reflux. The resulting mixture was stirred under reflux for 4 h and dried under vacuum. (b) The residue was dissolved in 200 mL of dichloroethane and treated with anhydrous ammonia gas at room temperature. (c) After removing solvent, the intermediate 5-substituted-2-nitrobenzamide (2a,b) was dissolved in MeOH and hydrogenated over 10percent Pd/C for 1-2 h. The catalyst was removed by filtration, and the solution was dried under vacuum to afford the 5-substituted-2-aminobenzamides as pale yellow powders (3a: 0.7 g, 85percent; 3b: 0.8 g, 85percent).
Reference: [1] Patent: WO2006/34491, 2006, A2, . Location in patent: Page/Page column 43
[2] Patent: WO2014/143960, 2014, A1, . Location in patent: Page/Page column 40
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2709 - 2721
  • 6
  • [ 61272-77-3 ]
  • [ 63069-49-8 ]
YieldReaction ConditionsOperation in experiment
79% With water; potassium carbonate In water at 150℃; for 0.5 h; Microwave irradiation General procedure: Adapted from a literature procedure,1 the appropriate organonitrile (1.0 eq.) and K2CO3(0.2eq.)wereaddedtoamicrowavetubewithastir-barwithdeionizedwater(8.5mLpermmolsubstrate).Afterirradiationundermicrowaveat150°Cfor30minutes,thereactionmixturewascooled,extractedwithEtOAc(320mL),thecombinedphasesdriedoverMgSO4andexcesssolventremovedinvacuo.TheresiduewaspurifiedbyFCC,ifrequired,togivethetitlecompound.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 1, p. 135 - 144
  • 7
  • [ 443-69-6 ]
  • [ 63069-49-8 ]
Reference: [1] Patent: WO2006/28904, 2006, A1, . Location in patent: Page/Page column 113-114
[2] Patent: US2008/167305, 2008, A1, . Location in patent: Page/Page column 40
  • 8
  • [ 319-24-4 ]
  • [ 63069-49-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 235 - 252
  • 9
  • [ 320-98-9 ]
  • [ 63069-49-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2709 - 2721
[2] Patent: WO2014/143960, 2014, A1,
  • 10
  • [ 394-02-5 ]
  • [ 63069-49-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2709 - 2721
[2] Patent: WO2014/143960, 2014, A1,
  • 11
  • [ 63069-49-8 ]
  • [ 1262888-28-7 ]
Reference: [1] Molecules, 2017, vol. 22, # 2,
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