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[ CAS No. 5900-59-4 ] {[proInfo.proName]}

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Chemical Structure| 5900-59-4
Chemical Structure| 5900-59-4
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Product Details of [ 5900-59-4 ]

CAS No. :5900-59-4 MDL No. :MFCD09042792
Formula : C7H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :QNEJYHVIYJFNHC-UHFFFAOYSA-N
M.W : 170.60 Pubchem ID :12374837
Synonyms :

Calculated chemistry of [ 5900-59-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.95
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) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.95
Log Po/w (XLOGP3) : 0.92
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 0.9
Consensus Log Po/w : 1.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.81
Solubility : 2.61 mg/ml ; 0.0153 mol/l
Class : Very soluble
Log S (Ali) : -1.96
Solubility : 1.88 mg/ml ; 0.011 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.24
Solubility : 0.984 mg/ml ; 0.00577 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.06

Safety of [ 5900-59-4 ]

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

Application In Synthesis of [ 5900-59-4 ]

* 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 [ 5900-59-4 ]
  • Downstream synthetic route of [ 5900-59-4 ]

[ 5900-59-4 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 5900-59-4 ]
  • [ 31374-18-2 ]
YieldReaction ConditionsOperation in experiment
77% With hydrogenchloride In water; trimethyl orthoformate Reference example 2: 7-chloro-4(3H)-quinazolone
2-Amino-4-chlorobenzamide (25.6 g, 0.150 mol) obtained in Reference example 1 was dissolved in trimethyl orthoformate (560 ml), and to this added was concentrated hydrochloric acid (15 ml), and the mixture was stirred at room temperature for 1 hour.
After completion of the reaction, the reaction solution was filtered, and the crude crystal filtered was suspended in water (250 ml) and neutralized with 3N NaOH aqueous solution.
The neutralized solution was filtered, the solid being washed with water on the funnel to give 20.9 g (yield 77percent) of the title compound as white crystal.
Reference: [1] Patent: EP1229025, 2002, A1,
  • 2
  • [ 67-56-1 ]
  • [ 5900-59-4 ]
  • [ 31374-18-2 ]
YieldReaction ConditionsOperation in experiment
70% at 130℃; for 2 h; Inert atmosphere; Microwave irradiation 2-Amino-4-chlorobenzamide (85 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO)(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.The tube was nitrogen protected and placed in a single mode pressure microwave synthesizer (Discover CEM, USA). After the reaction mixture was reacted at 130 ° C for 2 hours, it was cooled 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: 70percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0070; 0071; 0072; 0073
  • 3
  • [ 5900-59-4 ]
  • [ 144-62-7 ]
  • [ 31374-18-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1337 - 1342
  • 4
  • [ 5900-59-4 ]
  • [ 122-51-0 ]
  • [ 31374-18-2 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 184
  • 5
  • [ 123-91-1 ]
  • [ 5900-59-4 ]
  • [ 122-51-0 ]
  • [ 31374-18-2 ]
Reference: [1] Patent: US2003/64986, 2003, A1,
  • 6
  • [ 5900-59-4 ]
  • [ 149-73-5 ]
  • [ 31374-18-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
  • 7
  • [ 5900-59-4 ]
  • [ 2148-57-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
  • 8
  • [ 5900-59-4 ]
  • [ 89-77-0 ]
Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
  • 9
  • [ 5900-59-4 ]
  • [ 53449-14-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
  • 10
  • [ 5900-59-4 ]
  • [ 5900-58-3 ]
Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
  • 11
  • [ 89-77-0 ]
  • [ 5900-59-4 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2 h;
Stage #2: at 0 - 20℃; for 1 h;
To a solution of 2-amino-4-chlorobenzoic acid 11 (3.4 g,20 mmol) and HOBt (3.0 g, 22 mmol) in DMF (50 mL) was addedEDCI (4.6 g, 24 mmol). The mixture was stirred at rt for 2 h. Theresulting solution was cooled to 0 °C, then 25percent ammonia solution(20 mL) was added. The mixture was warmed to ambient temperatureand stirred for 1 h. The reaction mixture was poured intocrushed ice, filtered and washed with water to give 12 (3.0 g, 88percentyield) as gray solid. 1H NMR (400 MHz, DMSO‑d6) δ: 7.77 (s, 1H),7.54 (d, J = 8.5 Hz, 1H), 7.14 (s, 1H), 6.82 (s, 2H), 6.74 (d, J = 2.1 Hz,1H), 6.49 (dd, J = 8.5, 2.1 Hz, 1H). 13C NMR (101 MHz, DMSO‑d6) δ:170.90, 151.98, 136.78, 131.06, 115.55, 114.45, 112.86 ppm. MS(ESI APCI) m/z 171.0 [M+H]+.
87.6%
Stage #1: With benzotriazol-1-ol In N,N-dimethyl-formamide for 0.166667 h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2 h;
Stage #3: With ammonium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 2 h;
Method I: 2-Amino-4-chlorobenzamide (ii-b)
To a mixture of 2-amino-4-chlorobenzoic acid (3.42 g, 20 mmol) in DMF (45 mL) was added HOBt (2.70 g, 20 mmol).
After stirring for 10 min, EDC hydrogen chloride (3.82 g, 20 mmol) was added to the mixture.
The resulted mixture was stirred at room temperature for 2 h. NH4OH (28percent, 5 mL) was added at 0° C. with vigorous stirring.
After addition, the mixture was stirred at room temperature for another 2 h.
The reaction mixture was added to water (200 mL) dropwise with stirring, then a precipitate formed.
The precipitate was collected and dried in vacuo to give 2.98 g of ii-b as a grey solid (87.6percent yield). LCMS m/z=171.0 (M+1), 173.0 (M+3) (Method B) (retention time=1.39 min).
1H NMR (400 MHz, DMSO-d6): δ 7.27 (d, J=9.6 Hz, 1H), 6.68 (d, J=2.4 Hz, 1H), 6.60 (dd, J=8.4, 2.0 Hz, 1H), 5.50-5.82 (m, 4H).
87.6%
Stage #1: With benzotriazol-1-ol In N,N-dimethyl-formamide for 0.166667 h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2 h;
Stage #3: With ammonium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 2 h;
HOBt (2.70 g, 20 mmol) was added to a mixture of 2-amino-4-chlorobenzoic acid (3.42 g, 20 mmol) in DMF (45 mL).After stirring for 10 minutes, EDC hydrogen chloride (3.82 g, 20 mmol) was added to the mixture. The resulting mixture was stirred at room temperature for 2 hours.NH 4 OH (28percent, 5 mL) was added at 0 ° C. with vigorous stirring.After the addition, the mixture was stirred at room temperature for a further 2 hours.The reaction mixture was added dropwise to water (200 mL) with stirring, and a precipitate was formed. The precipitate was collected and dried in vacuo to give 2.98 g of ii-b as a gray solid (yield 87.6percent).
66% With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; N,N-dimethyl-formamide at 20℃; for 96 h; [00393] Step A: To solution of 2-amino-4-chlorobenzoic acid (4.4 g, 25.8 mmol) in degassed DMF (75 mL) were added successively HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.37 g, 28 mmol), and 2N NH3MeOH (18 mL, 36 mmol), and the solution was stirred at rt for 4 d. The mixture was concentrated under reduced pressure and the residue was partitioned between H2O (200 mL) and DCM (200 mL). The separated aqueous phase was extracted with DCM (2 X 200 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10-50percent EtOAc/hexanes to afford 2-amino-4-chlorobenzamide as a solid (2.91 g, 660Zo)-1H NMR (300 MHz, DMSO-J6) δ 6.50 (dd, J= 8.48, 2.26 Hz, 1 H), 6.75 (d, J = 2.26 Hz, 1 H), 6.84 (br s, 2 H), 7.18 (br s, 1 H), 7.48 - 7.63 (m, 1 H), 7.80 (br s, 1 H).

Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 1361 - 1375
[2] Patent: US2015/307477, 2015, A1, . Location in patent: Paragraph 1473
[3] Patent: JP6121658, 2017, B2, . Location in patent: Paragraph 1063; 1064; 1065
[4] Patent: WO2010/99379, 2010, A1, . Location in patent: Page/Page column 142
[5] Arkivoc, 2012, vol. 2012, # 8, p. 198 - 213
[6] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
[7] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
  • 12
  • [ 5900-58-3 ]
  • [ 5900-59-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 5, p. 754 - 765
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 25, p. 4053 - 4068
[3] Journal of the Chemical Society, 1948, p. 1713
  • 13
  • [ 89-77-0 ]
  • [ 5900-59-4 ]
YieldReaction ConditionsOperation in experiment
66% With DIEA; benzotriazol-1-ol In N,N-dimethyl-formamide Step A:
To solution of 2-amino-4-chlorobenzoic acid (4.4 g, 25.8 mmol) in degassed DMF (75 mL) were added successively HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.37 g, 28 mmol), and 2N NH3/MeOH (18 mL, 36 mmol), and the solution was stirred at room temperature for 4 days.
The mixture was concentrated under reduced pressure and the residue was partitioned between H2O (200 mL) and DCM (200 mL).
The separated aqueous phase was extracted with DCM (2*200 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure.
The residue was purified by silica gel chromatography eluting with 10-50percent EtOAc/hexanes to afford 2-amino-4-chlorobenzamide as a solid (2.91 g, 66percent).
1H NMR (300 MHz, DMSO-d6) 86.50 (dd, J=8.48, 2.26 Hz, 1H), 6.75 (d, J=2.26 Hz, 1H), 6.84 (br s, 2H), 7.18 (br s, 1 H), 7.48-7.63 (m, 1H), 7.80 (br s, 1H).
Reference: [1] Patent: US2012/53176, 2012, A1,
  • 14
  • [ 89-77-0 ]
  • [ 1499-21-4 ]
  • [ 5900-59-4 ]
YieldReaction ConditionsOperation in experiment
68% With ammonium hydroxide; triethylamine In dichloromethane Reference example 1: 2-amino-4-chlorobenzamide
4-Chloroanthranilic acid (75 g, 0.437 mol) was suspended in dichloromethane (1.09 1).
To this suspension, triethylamine (73 ml, 0.524 mol) and diphenylphosphoryl chloride (141 g, 0.524 mol) were added successively, and the mixture was stirred at room temperature for 1 hour.
Then, 28percent aqueous ammonia (44 ml) was added, and the mixture was further stirred at room temperature for 2 hours.
After completion of the reaction, the reaction solution was filtrated, the filtrated crude crystal was washed with methanol to give 51.0 g (yield 68percent) of the title compound as yellow crystal.
Reference: [1] Patent: EP1229025, 2002, A1,
  • 15
  • [ 40928-13-0 ]
  • [ 5900-59-4 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
[2] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
  • 16
  • [ 34662-32-3 ]
  • [ 5900-59-4 ]
  • [ 28144-70-9 ]
Reference: [1] Synlett, 2014, vol. 25, # 10, p. 1403 - 1408
  • 17
  • [ 7439-89-6 ]
  • [ 497-19-8 ]
  • [ 41994-91-6 ]
  • [ 5900-59-4 ]
Reference: [1] Patent: US5187168, 1993, A,
  • 18
  • [ 1397833-65-6 ]
  • [ 5900-59-4 ]
Reference: [1] Arkivoc, 2012, vol. 2012, # 8, p. 198 - 213
  • 19
  • [ 34662-32-3 ]
  • [ 5900-59-4 ]
Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
  • 20
  • [ 89-63-4 ]
  • [ 5900-59-4 ]
Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
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