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Chemical Structure| 179688-01-8
Chemical Structure| 179688-01-8
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Product Details of [ 179688-01-8 ]

CAS No. :179688-01-8 MDL No. :MFCD04115119
Formula : C16H14N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZCUFFSHMOAEEIL-UHFFFAOYSA-N
M.W : 282.29 Pubchem ID :135404718
Synonyms :

Calculated chemistry of [ 179688-01-8 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.12
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 79.03
TPSA : 64.47 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 2.77
Log Po/w (MLOGP) : 1.92
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.75
Solubility : 0.0496 mg/ml ; 0.000176 mol/l
Class : Soluble
Log S (Ali) : -3.98
Solubility : 0.0298 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.54
Solubility : 0.000814 mg/ml ; 0.00000288 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.14

Safety of [ 179688-01-8 ]

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 [ 179688-01-8 ]

* 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 [ 179688-01-8 ]
  • Downstream synthetic route of [ 179688-01-8 ]

[ 179688-01-8 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
93.9% With trichlorophosphate In 1,2-dichloro-ethane at 85℃; for 1 h; 2.1 g of compound IV, 9.1 g of phosphorus oxytrichloride and 60 ml of dichloroethane were mixed and refluxed at 85 ° C for one hour,The phosphorous oxychloride was spin-removed, ice-water was added, and the mixture was extracted with methylene chloride. The organic phase was washed with saturated sodium chloride solution,Dried with magnesium sulfate, dried by suction filtration, and subjected to column chromatography, followed by using hexane: ethyl acetate volume ratio = 5: 1,3: 1 and 1: 1 gradient elution, in n-hexane: ethyl acetate volume ratio = 1: 1 elution was in theTo 2.1 g of an off-white solid (Compound 5) in a yield of 93.9percent
88.6% With pyridine; thionyl chloride In N,N-dimethyl-formamide for 1 h; Reflux Compound 7 (860mg, 3.04mmol) was added to thionyl chloride (9.5mL) with magnetic stirring. DMF (0.2mL) and pyridine (0.23mL) were then added dropwise and the mixture was heated to reflux for 1h. Isolation was performed by the slow addition of the reaction medium over a mixture of ice and water with vigorous stirring. The resulting precipitate was filtered under a vacuum and dried to give 8 (810mg, 88.6percent) as yellow powder. Mp: 132–134°C; 1H NMR (DMSO-d6, 300MHz): δ (ppm) 3.99 (s, 3H), 5.36 (s, 2H), 7.37–7.56 (m, 7H), 8.87 (s, 1H).
88.6% With pyridine; thionyl chloride In N,N-dimethyl-formamide for 1 h; Reflux 9.5 ml of SOCl2(860 mg, 3.04 mmol) was added, and 0.2 ml of DMF was added dropwise with stirring. Pyridine (0.23 ml) was slowly added dropwise, followed by the addition of a solution of 4-hydroxy- And the mixture was heated under reflux for 1 hour.The reaction was complete, cooled to room temperature, slowly dropping into 50ml of ice water, stirring, precipitation of yellow solid, filtration, water washing filter cake, drying 810mg, 4-chloro-6-methoxy-7-benzyloxy quinazoline, yieldpercent 88.6,
Reference: [1] Patent: CN105541736, 2016, A, . Location in patent: Paragraph 0044; 0049
[2] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 245 - 254
[3] Patent: CN105884699, 2016, A, . Location in patent: Paragraph 0062; 0063
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5342 - 5346
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  • [ 162364-72-9 ]
YieldReaction ConditionsOperation in experiment
90% With thionyl chloride In N,N-dimethyl-formamide for 1 h; Heating / reflux b)
Dimethylformamide (0.2 ml) was added dropwise to a solution of 6-methoxy-7-benzyloxy-3,4-dihydroquinazolin-4-one (5.00 g, 17.9 mmol) in thionyl chloride (100ml) and the reaction was heated at reflux for 1 hour.
The reaction was cooled, excess thionyl chloride was removed in vacuo and the residue was azeotroped with toluene (3 x 50 ml) to remove the last of the thionyl chloride.
The residue was taken up in dichloromethane (550 ml), the solution was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and water (100 ml) and the organic phase was dried over magnesium sulphate.
Solvent evaporation in vacuo yielded 4-chloro-6-methoxy-7-benzyloxyquinazoline (4.80 g, 90 percent yield) as a pale brown solid:
1H-NMR (DMSO d6): 8.85 (s,1H), 7.58 (s, 1H), 7.50 (d, 2H), 7.40 (m, 4H), 5.35 (s, 2H), 4.00 (s, 3H):
MS (+ve ESI): 301 (M+H)+.
90% for 1 h; Heating / reflux b)
Dimethylformamide (0.2 ml) was added dropwise to a solution of 6-methoxy-7-benzyloxy-3,4-dihydroquinazolin-4-one (5.00 g, 17.9 mmol) in thionyl chloride (100 ml) and the reaction was heated at reflux for 1 hour.
The reaction was cooled, excess thionyl chloride was removed in vacuo and the residue was azeotroped with toluene (3*50 ml) to remove the last of the thionyl chloride.
The residue was taken up in dichloromethane (550 ml), the solution was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and water (100 ml) and the organic phase was dried over magnesium sulphate.
Solvent evaporation in vacuo yielded 4-chloro-6-methoxy-7-benzyloxyquinazoline (4.80 g, 90percent yield) as a pale brown solid:
1H-NMR (DMSO d6): 8.85 (s, 1H), 7.58 (s, 1H), 7.50 (d, 2H), 7.40 (m, 4H), 5.35 (s, 2H), 4.00 (s, 3H):
MS (+ve ESI): 301 (M+H)+.
86% for 16 h; Reflux 7-(Benzyloxy)-6-methoxyquinazolin-4(3H)-one (8 g, 24.1 mmol, 1.00 equiv) was dissolved in a solution of thionyl chloride (200 mL) and N,N-dimethylformamide (1 mL).
The solution was heated at reflux for about 16 hours and then concentrated in vacuo.
The resulting crude residue was then purified by silica gel column chromotagraphy (dichloromethane/ethyl acetate 2:1) to give the title product as a white solid (6.9 g, yield 86percent). LC-MS: m/z=301/303 (MH)+.
65% for 3 h; Heating / reflux Step 2e.
7-(Benzyloxy)-4-chloro-6-methoxyquinazoline (Compound 206)
A mixture of compound 205 (6.5 g, 8.5 mmol) and phosphoryl trichloride (40 mL) was stirred and heated to reflux for 3 hours.
When a clear solution was obtained, the excessive phosphoryl trichloride was removed under reduced pressure.
The residue was dissolved in dichloromethane (200 mL) and the organic layer was washed with aqueous NaHCO3 solution (100 mL*3) and brine (100 mL*1) and dried over MgSO4, filtered and evaporated to give the title compound 206 as a yellow solid (1.4 g, 65percent): LCMS: 301[M+1]+.
48% With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane; chloroform at 0℃; for 2 - 3 h; Heating / reflux Dry DMF (8. 0ml, 103mmol) was dissolved in dry CHC13 (40ml) and cooled in an ice bath. Oxalyl chloride (9. Oml, 105MMOL) in CH2C12 (10ML) was added dropwise with stirring at OC. When the bubbling had ceased, this solution was added slowly to an ice-cold solution of 7-benzyloxy-6- methoxy-3H-quinazolin-4-one (LO. OG, 35.4mmol) in dry CHC13 (60ml) and the mixture was then heated to reflux for 2-3hrs. After cooling to room temperature, H20 (100MI) was added and the phases were separated. The aqueous phase was further extracted with CHC13 (2x). The combined CHC13 extractions were washed with sat'd NaCl (LX), dried (NA2S04) and concentrated in vacuo. The resulting residue was purified by flash chromatography (1: 1 hexanes: EtOAc, followed by 100percent EtOAc) to give 7-benzyloxy-4- chloro-6-methoxy-quinoline (5. 1 LG, 48percent).
48% With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane; chloroform at 0℃; for 2 - 3 h; Heating / reflux Dry DMF (8. 0ml, 103mmol) was dissolved in dry CHC13 (40ml) and cooled in an ice bath. Oxalyl chloride (9. Oml, 105MMOL) in CH2C12 (10ML) was added dropwise with stirring at OC. When the bubbling had ceased, this solution was added slowly to an ice-cold solution of 7-benzyloxy-6- methoxy-3H-quinazolin-4-one (LO. OG, 35.4mmol) in dry CHC13 (60ml) and the mixture was then heated to reflux for 2-3hrs. After cooling to room temperature, H20 (100MI) was added and the phases were separated. The aqueous phase was further extracted with CHC13 (2x). The combined CHC13 extractions were washed with sat'd NaCl (LX), dried (NA2S04) and concentrated in vacuo. The resulting residue was purified by flash chromatography (1: 1 hexanes: EtOAc, followed by 100percent EtOAc) to give 7-benzyloxy-4- chloro-6-methoxy-quinoline (5. 1 LG, 48percent).

Reference: [1] Patent: EP1153920, 2001, A1,
[2] ChemMedChem, 2014, vol. 9, # 7, p. 1476 - 1487
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 23, p. 4910 - 4925
[4] Patent: EP1218357, 2005, B1, . Location in patent: Page/Page column 23
[5] Patent: US7081461, 2006, B1, . Location in patent: Page/Page column 40
[6] Patent: US2010/75916, 2010, A1, . Location in patent: Page/Page column 16
[7] Patent: US2009/76044, 2009, A1, . Location in patent: Page/Page column 27
[8] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3772 - 3793
[9] Patent: WO2005/30140, 2005, A2, . Location in patent: Page/Page column 196
[10] Patent: WO2005/30140, 2005, A2, . Location in patent: Page/Page column 196
[11] Patent: US6414148, 2002, B1,
[12] Patent: US6593333, 2003, B1,
[13] Patent: WO2007/36713, 2007, A2, . Location in patent: Page/Page column 49
[14] Patent: WO2007/36713, 2007, A2, . Location in patent: Page/Page column 53; 54; 55; 56
[15] Patent: WO2007/36713, 2007, A2, . Location in patent: Page/Page column 54; 55
[16] Patent: WO2007/36713, 2007, A2, . Location in patent: Page/Page column 52; 53; 55
[17] Patent: US2004/48881, 2004, A1,
[18] Patent: WO2008/53221, 2008, A2, . Location in patent: Page/Page column 45-46
[19] Patent: US2003/225111, 2003, A1, . Location in patent: Page 34
[20] Patent: US2003/225111, 2003, A1, . Location in patent: Page 43, 44
[21] Patent: WO2004/4732, 2004, A1, . Location in patent: Page/Page column 67; 73
[22] Patent: US6806274, 2004, B1, . Location in patent: Page column 73
[23] Patent: US6806274, 2004, B1, . Location in patent: Page/Page column 57
[24] Patent: WO2005/13998, 2005, A1, . Location in patent: Page/Page column 75
[25] Patent: WO2010/85747, 2010, A1, . Location in patent: Page/Page column 53
[26] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1053 - 1056
[27] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4080 - 4083
[28] Patent: WO2006/117552, 2006, A1, . Location in patent: Page/Page column 64; 66
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Reference: [1] Patent: US6265411, 2001, B1,
  • 4
  • [ 179688-01-8 ]
  • [ 196603-96-0 ]
Reference: [1] Patent: WO2012/30160, 2012, A2,
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4080 - 4083
  • 5
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  • [ 196603-96-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5369 - 5389
  • 6
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  • [ 768350-54-5 ]
Reference: [1] Patent: WO2012/30160, 2012, A2,
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4080 - 4083
  • 7
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  • [ 768350-54-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5369 - 5389
  • 8
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  • [ 162012-72-8 ]
YieldReaction ConditionsOperation in experiment
88% for 3 h; Reflux Compound 122 (247 g, 875.6 mmol) was dissolved in trifluoroacetic acid (800 mL), and CH3SO3H (127 mL) was added in one portion. The reaction was heated to reflux for 3 h, then cooled to room temperature and concentrated. Aqueous 2.5 N NaOH was added to adjust the pH of the solution to 7, which caused precipitation. The resultant solid was crushed, was stirred vigorously for 1 h, and was then filtered. The solid was collected and dried under high vacuum to afford 123 (148 g, yield=88percent) as brown solid.
64% With ammonium formate In DMF (N,N-dimethyl-formamide) for 1.75 h; a) Palladium on carbon (3.3g of a 10 percent mixture) was added to a solution of 7- (BENZYLOXY)-6-METHOXYQUINAZOLIN-4- (3H)-ONE (20 g, 71 mmol) (prepared according to J. Med. CHENU. 1999, 42, 5369-5389) was suspended in dimethylformamide (530 ml). Ammonium formate (45 g, 710 mmol) was then added portion wise over 1.25 hours. The reaction mixture was stirred for an additional 0.5 hours and the catalyst was removed by filtration. The solvent was removed IN VACUO to yield 7-HYDROXY-6-METHOXYQUINAZOLIN-4- (3H)-ONE (8. 65 g, 64 percent yield): 1H-NMR (DMSO D6) : 7.91 (s, 1H), 7.45 (s, 1H), 7.01 (s, 1H), 3.90 (s, 3H).
64% With ammonium formate In DMF (N,N-dimethyl-formamide) for 1.75 h; Palladium on carbon (3.3 g of a 10 percent mixture) was added to a solution of 7- (BENZYLOXY)-6-METHOXYQUINAZOLIN-4- (3H)-ONE (20 g, 71 mmol) (prepared according to J. Med. CHEZ. 1999,42, 5369-5389) suspended in dimethylformamide (530 ml). Ammonium formate (45 g, 710 mmol) was then added portion-wise over 1.25 hour. The reaction mixture was stirred for an additional 0.5 hour and the catalyst was removed by filtration. The solvent was removed IN VACUO to yield 7-HYDROXY-6-METHOXYQUINAZOLIN-4- (3H)-ONE (8.65 g, 64 percent yield): H-NMR (DMSO D6) : 7.91 (s, 1H), 7.45 (s, 1H), 7.01 (s, 1H), 3.90 (s, 3H).
60% With ammonium formate In DMF (N,N-dimethyl-formamide) at 20 - 80℃; for 2 h; 10percent Palladium on carbon (8.3g) was added to a suspension of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (50 g, 0.177 mol) in DIMETHYLFORMAMIDE (800 ml) under nitrogen. Ammonium formate (111.8 g, 1.77 mol) was then added in portions over 5 minutes. The reaction mixture was stirred for one hour at ambient temperature then heated to 80°C for a further hour. The reaction mixture was filtered hot through diatomaceous earth and the residues washed with DIMETHYLFORMAMIDE. The filtrate was then concentrated and the residue suspended in water. The pH was adjusted to 7.0 using 2M sodium hydroxide and the resulting mixture was stirred at ambient temperature for one hour. The solid was filtered, washed with water and dried over phosphorus pentoxide yielding 7-hydroxy-6-methoxy-3, 4-DIHYDROQUINAZOLIN-4-ONE as a white solid (20. 52 g, 60percent). 1H NMR Spectrum: (DMSOD6) 3.85 (s, 3H), 6.95 (s, 1H), 7.40 (s, 1H), 7.85 (s, 1H) MS-ESI: 193 [M+H] +
60% With ammonium formate In DMF (N,N-dimethyl-formamide) at 20 - 80℃; for 2.08333 h; Heating 10percent Palladium on carbon (8.3g) was added to a suspension of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (50 g, 0.177 mol) in DIMETHYLFORMAMIDE (800 ml) under nitrogen. Ammonium formate (111.8 g, 1.77 mol) was then added in portions over 5 minutes. The reaction mixture was stirred for one hour at ambient temperature then heated to 80°C for a further hour. The reaction mixture was filtered hot through diatomaceous earth and the residues washed with DIMETHYLFORMAMIDE. The filtrate was then concentrated and the residue suspended in water. The pH was adjusted to 7.0 using 2M sodium hydroxide and the resulting mixture was stirred at ambient temperature for one hour. The solid was filtered, washed with water and dried over phosphorus pentoxide yielding 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one as a white solid (20.52 g, 60percent). 1H NMR Spectrum : (DMSOd6) 3.85 (s, 3H), 6.95 (s, 1H), 7.40 (s, 1H), 7.85 (s, 1H) MS-ESI: 193 [M+H] +

Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 43, p. 7381 - 7384
[2] Patent: US2014/235634, 2014, A1, . Location in patent: Paragraph 0390; 0395
[3] Patent: WO2004/94410, 2004, A1, . Location in patent: Page 122
[4] Patent: WO2004/113324, 2004, A1, . Location in patent: Page 52
[5] Patent: WO2005/13998, 2005, A1, . Location in patent: Page/Page column 60
[6] Patent: WO2005/14582, 2005, A1, . Location in patent: Page/Page column 70
[7] Patent: WO2004/41829, 2004, A1, . Location in patent: Page 65
[8] Patent: WO2004/56812, 2004, A1, . Location in patent: Page 63
[9] Patent: WO2004/56801, 2004, A1, . Location in patent: Page 61
[10] Patent: WO2004/81000, 2004, A1, . Location in patent: Page 59
[11] Patent: WO2004/108711, 2004, A1, . Location in patent: Page 57
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