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Product Details of [ 162012-72-8 ]

CAS No. :162012-72-8 MDL No. :MFCD08458441
Formula : C9H8N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZHLRYPLSYOYNQM-UHFFFAOYSA-N
M.W : 192.17 Pubchem ID :135609952
Synonyms :

Calculated chemistry of [ 162012-72-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.88
TPSA : 75.21 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) : -7.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.14
Log Po/w (XLOGP3) : 0.32
Log Po/w (WLOGP) : 0.64
Log Po/w (MLOGP) : 0.3
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.7
Solubility : 3.87 mg/ml ; 0.0202 mol/l
Class : Very soluble
Log S (Ali) : -1.46
Solubility : 6.62 mg/ml ; 0.0345 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.79
Solubility : 0.311 mg/ml ; 0.00162 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 162012-72-8 ]

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 [ 162012-72-8 ]

* 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 [ 162012-72-8 ]
  • Downstream synthetic route of [ 162012-72-8 ]

[ 162012-72-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 179688-01-8 ]
  • [ 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
  • 2
  • [ 848092-84-2 ]
  • [ 77287-34-4 ]
  • [ 162012-72-8 ]
YieldReaction ConditionsOperation in experiment
85% at 140℃; for 4 h; A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol) was heated to 140C for 4 h. After cooling to r.t., water (75 mL) was added. Afterstirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one was filtered off, washed with waterand dried (grey solid, 5.86 g, 30.5 mmol, 85 percent). LC/ESI-MS: m/ z = 193 [M +H]+; m/ z = 191 [M-H]-; Rt = 1.53 min.
85% at 140℃; for 4 h; A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol) was heated to 140°C for 4 h. After cooling to r.t., water (75 mL) was added. After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one was filtered off, washed with water and dried (grey solid, 5.86 g, 30.5 mmol, 85 percent). LC/ESI-MS: m/z = 193 [M +H]+; m/z = 191 [M-H]-; Rt = 1.53 min.
85% at 140℃; for 4 h; Step 4. A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol) was heated to 140° C. for 4 h. After cooling to r.t., water (75 mL) was added. After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one was filtered off, washed with water and dried (grey solid, 5.86 g, 30.5 mmol, 85percent). LC/ESI-MS: m/z=193 [M+H]+; m/z=191 [M-H]-; Rt=1.53 min.
76% at 140℃; for 4 h; Step 4.
A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and crude material of step 3 (36.0 mmol) was heated to 140° C. for 4 h.
After cooling to r.t., water (75 mL) was added.
After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one or 6-hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one, respectively, was filtered off, washed with water and dried (76-85percent).

Reference: [1] Patent: EP1674467, 2006, A1, . Location in patent: Page/Page column 26
[2] Patent: EP1674466, 2006, A1, . Location in patent: Page/Page column 26
[3] Patent: US2006/142570, 2006, A1, . Location in patent: Page/Page column 17
[4] Patent: US2007/149523, 2007, A1, . Location in patent: Page/Page column 13
[5] Patent: US2006/135782, 2006, A1, . Location in patent: Page/Page column 23
[6] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 18, p. 6728 - 6737
  • 3
  • [ 916606-81-0 ]
  • [ 162012-72-8 ]
YieldReaction ConditionsOperation in experiment
96% With peracetic acid; sulfuric acid In ethanol at 60℃; for 12 h; General procedure: To a solution of 6,7-dimethoxyquinazoline 1a (200.0 mg, 1.05 mmol) in ethanol (20 mL) were added 40percent peracetic acid (1.0mL, 5.26 mmol) and 0.01 mL sulfuric acid (1.8 mmol). After the reaction was stirred at 60°C for 4–12 h (see Table 2) and then cooled to room temperature, excess sodium bisulfite (541.8 mg, 5.26 mmol) was added to get rid of the peroxide. The solid was filtered off after stirring for 20 min, and the filtrate was concentrated under reduced pressure to give the crude product, which was washed by ethanol and petroleum ether to give 2a as a light yellow solid (179.7 mg, 83percent), mp>300°C.
Reference: [1] Synthetic Communications, 2014, vol. 44, # 3, p. 346 - 351
  • 4
  • [ 848092-84-2 ]
  • [ 16712-16-6 ]
  • [ 162012-72-8 ]
YieldReaction ConditionsOperation in experiment
86% at 150℃; for 5 h; 4.1.6
7-Hydroxy-6-methoxyquinazolin-4(3H)-one (14)
A mixture of formamide (25 mL), ammonium formate (3.59 g, 57 mmol) and 13 (6.5 g, 33 mmol) was heated at 150 °C for 5 h.
The mixture was cooled to room temperature, and water (100 mL) was added in order to precipitate the quinazolinone 14.
After stirring for 1 h, the resulting precipitate was filtered off, washed with water and dried to obtain intermediate 14 as a white solid. Yield: 86percent, mp: >250 °C.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 24, p. 6796 - 6805
  • 5
  • [ 848092-84-2 ]
  • [ 16712-16-6 ]
  • [ 77287-34-4 ]
  • [ 162012-72-8 ]
YieldReaction ConditionsOperation in experiment
76% at 140℃; for 4 h; Step 4. A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and crude material of step 3 (36.0 mmol) was heated to 140° C. for 4 h. After cooling to r.t., water (75 mL) was added. After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one or 6-hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one, respectively, was filtered off, washed with water and dried (76-85percent).
76% at 140℃; for 4 h; Step 4.
A mixture of formamide (29 mL), ammonium formate (3.41 g, 54 mmol) and crude material of step 3 (36.0 mmol) was heated to 140°C for 4 h.
After cooling to r.t., water (75 mL) was added.
After stirring for 1 h, the precipitated 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one or 6-hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one, respectively, was filtered off, washed with water and dried (76-85percent).
Reference: [1] Patent: US2007/21446, 2007, A1, . Location in patent: Page/Page column 14
[2] Patent: EP1785420, 2007, A1, . Location in patent: Page/Page column 18
[3] Patent: EP1746096, 2007, A1, . Location in patent: Page/Page column 24
  • 6
  • [ 3943-74-6 ]
  • [ 162012-72-8 ]
Reference: [1] Patent: US2014/235634, 2014, A1,
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 24, p. 6796 - 6805
[3] Patent: US2007/149523, 2007, A1,
  • 7
  • [ 56441-97-5 ]
  • [ 162012-72-8 ]
Reference: [1] Patent: US2014/235634, 2014, A1,
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 24, p. 6796 - 6805
[3] Patent: US2007/149523, 2007, A1,
  • 8
  • [ 61032-41-5 ]
  • [ 162012-72-8 ]
Reference: [1] Patent: US2014/235634, 2014, A1,
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 24, p. 6796 - 6805
[3] Patent: US2007/149523, 2007, A1,
  • 9
  • [ 741276-49-3 ]
  • [ 162012-72-8 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 3, p. 346 - 351
  • 10
  • [ 61032-42-6 ]
  • [ 162012-72-8 ]
Reference: [1] Patent: US2014/235634, 2014, A1,
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