[ CAS No. 42465-54-3 ] {[proInfo.proName]}

Name: 42465-54-3|1-(2-Amino-3-methoxyphenyl)ethanone|95%
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Quality Control of [ 42465-54-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 42465-54-3 ]

Product Details of [ 42465-54-3 ]

CAS No. :	42465-54-3	MDL No. :	MFCD11113373
Formula :	C₉H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RHVYWYRETWKHDC-UHFFFAOYSA-N
M.W :	165.19	Pubchem ID :	13691141
Synonyms :

Calculated chemistry of [ 42465-54-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.53
TPSA :	52.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.52
Log Po/w (XLOGP3) :	1.45
Log Po/w (WLOGP) :	1.49
Log Po/w (MLOGP) :	0.83
Log Po/w (SILICOS-IT) :	1.44
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.02
Solubility :	1.59 mg/ml ; 0.00965 mol/l
Class :	Soluble
Log S (Ali) :	-2.15
Solubility :	1.16 mg/ml ; 0.00701 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.49
Solubility :	0.531 mg/ml ; 0.00321 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.3

Safety of [ 42465-54-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 42465-54-3 ]

* 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 [ 42465-54-3 ]
Downstream synthetic route of [ 42465-54-3 ]

[ 42465-54-3 ] Synthesis Path-Upstream 1~7

1
[ 33852-43-6 ]
[ 42465-54-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron; acetic acid In ethanol at 0℃; for 3 h;	Example 35Preparation of 2-chloro-8-methoxy-4-methylquinazolhie The subject compound was prepared according to the general Scheme below:Step 1. Preparation of 3-methoxy-2-aminobenzaldehydeTo a 1 :1 mixture of ethanol and acetic acid was added 3-methoxy-2-nitrobenzaldehyde (leq) and Fe dust (3eq)was added in portions. The reduction was complete in 3h. The reaction mixture was filtered and then concentrated and partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate and dried and concentrated to give 2- amino-3-methoxybenzaldehyde in 85 percent yield. ES/MS m/z 151(MH⁺).

Reference： [1] Patent: WO2007/117607, 2007, A2, . Location in patent: Page/Page column 348
[2] Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6873 - 6877
[3] Patent: US4620000, 1986, A,
[4] Patent: US4666499, 1987, A,
[5] Patent: US2011/144115, 2011, A1, . Location in patent: Page/Page column 7
[6] Patent: US2012/129864, 2012, A1, . Location in patent: Page/Page column 8
[7] Patent: WO2013/50527, 2013, A1, . Location in patent: Page/Page column 47; 48

2
[ 4502-10-7 ]
[ 74-88-4 ]
[ 42465-54-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1 h;	a) 1-(2-Amino-3-methoxy-phenyl)-ethanone Under an atmosphere of nitrogen, methyl iodide (1.35 g, 10 mmol) and postassium carbonate (4.39 g, 320 mmol) were added to a solution of 2'-amino-3'-hydroxyacetophenone (960 mg, 6 mmol, TCI Europe) in DMF (6 ml). The reaction mixture was stirred for 1 h at r.t., during which time the color of the mixture changed from light brown to dark green. The mixture was then worked up by extraction with H₂O/ethyl acetate, drying of the organic phase (Na₂SO₄), and evaporation of solvent. The title compound (960 mg, 92percent) was isolated from the residue by column chromatography (silica gel, heptan/ethyl acetate=100/0-70/30). ¹H NMR (d⁶-DMSO):δ 2.50 (6H, s), 6.54 (1H, dd), 6.90 (2H, bs), 6.99 (1H, d), 7.36 (1H, d).

Reference： [1] Patent: US2006/293350, 2006, A1, . Location in patent: Page/Page column 6

3
[ 586-37-8 ]
[ 42465-54-3 ]

Reference： [1] Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6873 - 6877

4
[ 15865-57-3 ]
[ 42465-54-3 ]

Reference： [1] Patent: US2011/144115, 2011, A1,
[2] Patent: US2012/129864, 2012, A1,
[3] Patent: WO2013/50527, 2013, A1,

5
[ 4920-80-3 ]
[ 42465-54-3 ]

Reference： [1] Patent: US2011/144115, 2011, A1,
[2] Patent: US2012/129864, 2012, A1,
[3] Patent: WO2013/50527, 2013, A1,

6
[ 941-55-9 ]
[ 586-37-8 ]
[ 42465-54-3 ]
[ 23042-77-5 ]

Reference： [1] Chemical Communications, 2013, vol. 49, # 45, p. 5225 - 5227

7
[ 75-16-1 ]
[ 148932-68-7 ]
[ 42465-54-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 256 - 261

[ 42465-54-3 ] Synthesis Path-Downstream 1~88

1
[ 917-64-6 ]
[ 42465-54-3 ]
[ 873995-53-0 ]

Reference： [1]Journal of the Chemical Society,1952,p. 3009,3014

2
[ 42465-54-3 ]
phenylmagnesium bromide [ No CAS ]
[ 859033-51-5 ]

Reference： [1]Journal of the Chemical Society,1952,p. 3009,3014

3
[ 42465-54-3 ]
[ 135187-61-0 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1097,1098

4
[ 42465-54-3 ]
[ 4938-06-1 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1097,1098

5
[ 42465-54-3 ]
[ 189252-16-2 ]

Reference： [1]Journal of the Chemical Society,1952,p. 3009,3014
[2]Journal of Organic Chemistry,2016,vol. 81,p. 4645 - 4653

6
[ 42465-54-3 ]
[ 99184-73-3 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1097,1098

7
[ 42465-54-3 ]
[ 108-24-7 ]
[ 875258-00-7 ]

Reference： [1]Journal of the Chemical Society,1954,p. 4034

8
[ 42465-54-3 ]
[ 98-88-4 ]
[ 411209-87-5 ]

Reference： [1]Journal of the Chemical Society,1945,p. 646,655

9
[ 42465-54-3 ]
[ 75-36-5 ]
[ 875258-00-7 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1097,1098

10
[ 42465-54-3 ]
[ 67-64-1 ]
[ 84264-26-6 ]

Reference： [1]Journal of the Chemical Society,1945,p. 646,655

11
[ 42465-54-3 ]
[ 2258-42-6 ]
[ 408507-83-5 ]

Reference： [1]Journal of the Chemical Society,1954,p. 505,506

12
[ 42465-54-3 ]
[ 3282-30-2 ]
[ 228878-05-5 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1645 - 1652

14
1-<2-nitro-3-methoxy-phenyl>-ethanone-(1) [ No CAS ]
[ 42465-54-3 ]

Reference： [1]Journal of the Chemical Society,1945,p. 646,655

15
[ 42465-54-3 ]
[ 57-13-6 ]
[ 953039-91-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With acetic acid; at 100℃; for 16h;	Step 2. Preparation of 8-methoxy-4-methylquinazolin-2-ol To methyl 2-antauino-3-methoxybenzaldehyde (leq) was added urea (5eq) and few ml of acetic acid the mixture was heated to 1000C for 16h. To the crude was added water and the precipitated solid was filtered to give methyl 8-methoxy-4-methylquinazolin-2-pl in quantitative yield. ES/MS m/z 191(MH+).

Reference： [1]Patent: WO2007/117607,2007,A2 .Location in patent: Page/Page column 348

16
[ 42465-54-3 ]
[ 693-02-7 ]
[ 950818-63-0 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6873 - 6877
[2]Journal of Organic Chemistry,2008,vol. 73,p. 4971 - 4977
[3]Tetrahedron,2009,vol. 65,p. 8507 - 8512

17
[ 917-92-0 ]
[ 42465-54-3 ]
[ 950818-71-0 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6873 - 6877
[2]Journal of Organic Chemistry,2008,vol. 73,p. 4971 - 4977

18
[ 33852-43-6 ]
[ 42465-54-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron; acetic acid; In ethanol; at 0℃; for 3h;	Example 35Preparation of 2-chloro-8-methoxy-4-methylquinazolhie The subject compound was prepared according to the general Scheme below:Step 1. Preparation of 3-methoxy-2-aminobenzaldehydeTo a 1 :1 mixture of ethanol and acetic acid was added 3-methoxy-2-nitrobenzaldehyde (leq) and Fe dust (3eq)was added in portions. The reduction was complete in 3h. The reaction mixture was filtered and then concentrated and partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate and dried and concentrated to give 2- amino-3-methoxybenzaldehyde in 85 % yield. ES/MS m/z 151(MH+).
	With iron; In water; ethyl acetate;	16.35 g of 5A was suspended in 220 ml of a 1:1 v:v mixture of ethyl acetate and water. 18.9 g of iron filings was added in portions over about 30 minutes. The resulting mixture was refluxed for 1.5 hours, diluted with water and extracted with ethyl acetate. The extract was washed with water, sodium carbonate solution, water, brine, dried (Na2 SO4), and the solvent was evaporated. The residue was chromatographed over silica gel using a 1:1 v:v mixture of ethyl acetate and hexane as eluent. One set of fractions was collected and stripped. The residue was dissolved in ethyl acetate, part of which then was evaporated, and the remainder was allowed to stand at room temperature. Solid material that formed was separated to give 2-amino-3-methoxyacetophenone (5B), as a pale green solid, m.p.: 61.5-63 C.
	With iron; acetic acid; In water;	21.95 g of 4A was suspended in 220 ml of a 1:1 v:v mixture of acetic acid and water at room temperature. Then 18.90 g of iron filings were added in portions over 0.5 hour. The mixture was refluxed for 1.5 hours and diluted with water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, dilute aqueous sodium carbonate solution, dried (Na2 SO4) and the solvent was evaporated. The residue was chromatographed on silica gel, using a 1:1 v:v mixture of ethyl acetate and hexane as eluent, to give 2-amino-3-methoxyacetophenone (4B), as a green solid, m.p.: 48-49 C.

	With acetic acid; zinc; In tetrahydrofuran; at 0 - 20℃; for 4h;	C-1-(2-Amino-3-methoxyphenyl)ethanoneA solution of 3.3 g of the compound from the preceding stage in 100 ml of THF is cooled to 0 C., 13.27 g of zinc and 15 ml of acetic acid are added, the mixture is then left stirring while allowing the temperature to rise to AT and is left stirring at AT for 4 hours. The reaction mixture is filtered through Celite and the filtrate is concentrated under vacuum. The residue is extracted with THF, the organic phase is washed with 100 ml of a 10% NaOH solution and with a saturated NaCl solution and dried over MgSO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with the gradient of the cyclohexane/AcOEt mixture from 80/20 (v/v) to 60/40 (v/v). 2 g of the expected compound are obtained
		C-1-(2-Amino-3-methoxyphenyl)ethanone A solution of 3.3 g of the compound from the preceding stage in 100 ml of THF is cooled to 0 C., 13.27 g of zinc and 15.7 ml of acetic acid are added, the mixture is then left stirring while allowing the temperature to rise to AT and is left stirring at AT for 4 hours. The reaction mixture is filtered through Clite and the filtrate is concentrated under vacuum. The residue is extracted with THF, the organic phase is washed with 100 ml of a 10% NaOH solution and with a saturated NaCl solution and dried over MgSO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with the gradient of the cyclohexane/AcOEt mixture from 80/20 (v/v) to 60/40 (v/v). 2 g of the expected compound are obtained.
	With iron; acetic acid; at 70℃; for 4h;	Synthesis of 2-chloro-8-methoxy-4-methyl-quinazoline 5d To a solution of the compound 5 (2.0g, 0.01 mol) in 30 mL of anhydrous CH2CI2 was added SOCI2 (4.4 ml, 0.062 mol) and DMF (0.2 mL), then themixture was stirred at 60C for 3 hours. The resulting mixture was concentratedin vacuum to give compound 5a (2.1 g, yield: 95.5%) as ayellow solid, which was used for next step without further purification.To a solution of Mg (0.26 g, 0.01 1mol) in 30 mL of anhydrous THF was added EtOH (0.4 g) and CCI4 (0.2 mL) at 50C. After being stirred for 30min, a solution of 1A (1 .76 g, 0.01 1 mol)and EtOH (0.65 g) in 10 mL of anhydrous THFwas added, the mixture was stirred at 60C for 2 hours. To this solution wasadded a solution of compound 5a (2.1 g, 0.01mol) in 10 mL of THF, the mixture wasstirred at 60C for 1 hour. The reaction mixture was cooled and quenched with 10 ml of aqueous H2SO4 (10%), the organic layers were concentrate in vacuum to give a yellow oil. To this oil was added a mixture of CH3COOH (15 mL), H2SO4 (2 mL) and H2O (10 mL),the mixture was stirred at reflux for 16 hours. The resulting mixture wasextracted with EtOAc (50 mL chi 3), the organic layers were concentrated toafford crude compound 5b (1 .4 g, yield: 73.7%). m/z = 196 [M + H]+ .To a solution of compound 5b (1 .2 g,6.15 mmol) in 20 mL of CH3COOH was addediron power (1 .0 g, 18.5 mmol), then the suspension was stirred at 70C for 4hours. The resulting mixture was filtered through apad of celite, the filtrate was neutralized with aqueous NaOH till pH = 7,extracted with EtOAc (50 mL x 3), the organic layers were concentrated toafford crude compound 5c (0.9 g, yield: 90%). m/z = 166 [M + H]+ .To a solution of the compound 5c(0.85 g, 5.15 mmol) in 20 mL of THF was added DMAP (0.69 g, 5.67 mmol) andCI3CCOCI (0.63 mL, 5.67 mmol) at 0C, then the mixture was stirred at roomtemperature for 2 hours. The resulting mixture was diluted with ice water (50mL), extracted with EtOAc (50 mL x 3), the organic layers were concentrated invacuum to give compound 5d (1 .2 g, yield: 76%), which was used for next stepwithout further purification. No MS signal.To a solution of the compound 5d (1.5 g, 4.8 mmol) in 20 mL of DMSO was added CH3COONH (1 .85 g, 24 mmol), the mixture was stirred at room temperaturefor 20 hours. The resulting mixture was diluted with H2O (200 mL), extracted with EtOAc (50 mL chi 3),the organic layers were concentrated in vacuum to give 8-methoxy-4-methyl-1H-quinazolin-2-one (0.6 g, yield: 65.2%), which was used for next step withoutfurther purification. 1H NMR (DMSO-c/e400 MHz TMS): 51 1 .0 (s, 1 H), 7.50 (q, J = 8.4 Hz, 1 H), 7.30 (d, J = 7.6 Hz,1 H), 7.15-7.19 (m, 1 H), 3.90 (s, 3 H), 2.67 (s, 3 H). m/z = 191 [M + H]+ .To a solution of the compound8-methoxy-4-methyl-1 H-quinazolin-2-one (200 mg, 1 .05 mmol) in 15 mL oftoluene was added POCI3 (0.2 mL, 2.1 mmol) and DIPEA (0.38 mL, 2.1 mmol), thenthe mixture was stirred at 90C for 4 hours. The resulting mixture wasconcentrated in vacuum, the residue was extracted with Et2O (50 mL), the organic layer was collected anddried to give 2-chloro-8-methoxy-4-methyl-quinazoline (100 mg, yield: 45.8%).m/z = 209 [M + H]+ .

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6992 - 7014
[2]Patent: WO2007/117607,2007,A2 .Location in patent: Page/Page column 348
[3]Journal of Organic Chemistry,2007,vol. 72,p. 6873 - 6877
[4]Patent: US4620000,1986,A
[5]Patent: US4666499,1987,A
[6]Patent: US2011/144115,2011,A1 .Location in patent: Page/Page column 7
[7]Patent: US2012/129864,2012,A1 .Location in patent: Page/Page column 8
[8]Patent: WO2013/50527,2013,A1 .Location in patent: Page/Page column 47; 48

19
[ 42465-54-3 ]
[ 536-74-3 ]
[ 950818-67-4 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6873 - 6877
[2]Journal of Organic Chemistry,2008,vol. 73,p. 4971 - 4977

20
[ 42465-54-3 ]
2-butyl-8-methoxy-4-methylquinoline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6873 - 6877

21
[ 42465-54-3 ]
2-tert-butyl-8-methoxy-4-methylquinoline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6873 - 6877

22
[ 42465-54-3 ]
8-methoxy-4-methyl-2-phenylquinoline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6873 - 6877

23
[ 586-37-8 ]
[ 42465-54-3 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6873 - 6877
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 6992 - 7014

24
[ 42465-54-3 ]
2-(2-amino-3-methoxyphenyl)chromen-4-one [ No CAS ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1645 - 1652

25
[ 42465-54-3 ]
2-tert-butyl-8-methoxy-1,4-dihydroquinolin-4-one [ No CAS ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1645 - 1652

26
[ 42465-54-3 ]
[ 228878-07-7 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1645 - 1652

27
[ 42465-54-3 ]
[ 1027948-75-9 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1645 - 1652

28
[ 42465-54-3 ]
[ 17056-96-1 ]

Reference： [1]Journal of the Chemical Society,1952,p. 3009,3014

29
[ 42465-54-3 ]
[ 817209-14-6 ]

Reference： [1]Journal of the Chemical Society,1952,p. 3009,3014

30
[ 42465-54-3 ]
[ 194782-60-0 ]

Reference： [1]Journal of the Chemical Society,1952,p. 3009,3014

31
[ 42465-54-3 ]
[ 92644-01-4 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1097,1098

32
[ 42465-54-3 ]
[ 99512-70-6 ]

Reference： [1]Journal of the Chemical Society,1954,p. 505,506

33
[ 42465-54-3 ]
[ 69674-28-8 ]

Reference： [1]Journal of the Chemical Society,1954,p. 505,506

34
[ 42465-54-3 ]
[ 17056-97-2 ]

Reference： [1]Journal of the Chemical Society,1954,p. 4034

35
[ 42465-54-3 ]
8-methoxy-2,4-dimethyl-quinazoline [ No CAS ]

Reference： [1]Journal of the Chemical Society,1954,p. 4034

36
[ 42465-54-3 ]
[ 90417-27-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium acetate; sodium nitrite; In water;	3.30 g of 5B was suspended in a mixture of 20 ml of water, 20 g of ice and 4.5 ml of concentrated hydrochloric acid. Then, at 0 C., a solution of 1.45 g of sodium nitrite in 10 ml of water was added. After 25 minutes, 40 ml of chilled methylene chloride and a solution of 16.40 g of sodium acetate in 40 ml of water was added. The resulting mixture was stirred at about 12 C. overnight and filtered. The filtrate was dried under reduced pressure, then the solvent was evaporated to give 5, as a brown solid, m.p.: 160-163 C.
	With hydrogenchloride; sodium acetate; sodium nitrite; In water;	4.5 ml of concentrated hydrochloric acid was added to a suspension of 3.3 g of 4B in 20 ml of water and 20 g of ice, then a solution of 1.45 g of sodium nitrite in 10 ml of water was added, at 0 C. After 25 minutes, 40 ml of chilled methylene chloride and a solution of 16.40 g of sodium acetate in 40 ml of water was added. The mixture was stirred at -12 C. overnight, filtered and the collected solid was dried under reduced pressure to give 4-hydroxy-8-methoxycinnoline (4C), as a brown solid, m.p.: 160-163 C.

Reference： [1]Patent: US4620000,1986,A
[2]Patent: US4666499,1987,A
[3]Synthetic Communications,2020

37
hexahydroazepinone-⁽⁴⁾ hydrochloride [ No CAS ]
[ 42465-54-3 ]
7-methoxy-11-methyl-2,3,4,5-tetrahydro-1H-azepino[4,3-b]quinoline [ No CAS ]
7-methoxy-11-methyl-2,3,4,5-tetrahydro-1H-azepino[4,5-b]quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 57 1,2,4,5-Tetrahydro-11-methyl-7-methoxy-3H-azepino[4,5-b]quinoline, 2,3,4,5-tetrahydro-11-methyl-7-methoxy-1H-azepino[4,3-b]quinoline and their dihydochlorides were prepared from hexahydro-azepinone-(4) hydrochloride and <strong>[42465-54-3]2-amino-3-methoxy-acetophenone</strong> analogous to Example 1. Yield of the dihydrochloride of the [4,5-b]-isomer: 19% of theory; m.p. 260 C. (decomp.). Yield of the dihydrochloride of the [4,3-b]-isomer: 35% of theory; m.p. 224 C. (decomp.).

Reference： [1]Patent: US3987047,1976,A

38
[ 4502-10-7 ]
[ 74-88-4 ]
[ 42465-54-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1.0h;	a) 1-(2-Amino-3-methoxy-phenyl)-ethanone Under an atmosphere of nitrogen, methyl iodide (1.35 g, 10 mmol) and postassium carbonate (4.39 g, 320 mmol) were added to a solution of <strong>[4502-10-7]2'-amino-3'-hydroxyacetophenone</strong> (960 mg, 6 mmol, TCI Europe) in DMF (6 ml). The reaction mixture was stirred for 1 h at r.t., during which time the color of the mixture changed from light brown to dark green. The mixture was then worked up by extraction with H2O/ethyl acetate, drying of the organic phase (Na2SO4), and evaporation of solvent. The title compound (960 mg, 92%) was isolated from the residue by column chromatography (silica gel, heptan/ethyl acetate=100/0-70/30). 1H NMR (d6-DMSO):delta 2.50 (6H, s), 6.54 (1H, dd), 6.90 (2H, bs), 6.99 (1H, d), 7.36 (1H, d).

Reference： [1]Patent: US2006/293350,2006,A1 .Location in patent: Page/Page column 6

39
[ 42465-54-3 ]
[ 1066-54-2 ]
C₁₄H₂₁NO₂Si [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 4971 - 4977

40
[ 42465-54-3 ]
[ 333-20-0 ]
[ 918136-55-7 ]

Yield	Reaction Conditions	Operation in experiment
58%		b) 8-Methoxy-4-methyl-3,4-dihydro-1H-quinazoline-2-thione Under an atmosphere of nitrogen and at a temperature of 65 C., sodium borohydride (154 mg, 4 mmol) was added to a solution of <strong>[42465-54-3]1-(2-amino-3-methoxy-phenyl)-ethanone</strong> (960 mg, 6 mmol) in ethanol (8 ml). After stirring at 65 C. overnight, water (5 ml), a solution of potassium thiocyanate (620 mg, 6 mmol) in water (3 ml), and a solution of conc. HCl (3 ml) in water (4 ml) were added subsequently. The mixture was then stirred for an additional 3 h at 65 C. Upon cooling, the solvent was evaporated and the residue was taken up in water/ethyl acetate. The organic phase was dried (Na2SO4), and the solvent was evaporated. Chromatography (silica gel, heptan/ethyl acetate=100/0-70/30) gave the title compound (700 mg, 58%). 1H NMR (CDCl3):delta 1.53 (3H, d), 3.87 (3H, s), 4.73 (1H, q), 6.66 (1H, d), 6.77 (1H, d), 7.01 (1H, dd), 8.26 (2H, bs).

Reference： [1]Patent: US2006/293350,2006,A1 .Location in patent: Page/Page column 6
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 256 - 261

41
[ 75-16-1 ]
[ 148932-68-7 ]
[ 42465-54-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 256 - 261

42
[ 42465-54-3 ]
[ 1204652-09-4 ]

Reference： [1]Patent: US2011/144115,2011,A1

43
[ 42465-54-3 ]
[ 33844-20-1 ]

Reference： [1]Patent: US2011/144115,2011,A1

44
[ 42465-54-3 ]
[ 1204652-86-7 ]

Reference： [1]Patent: US2011/144115,2011,A1

45
[ 42465-54-3 ]
[ 90417-27-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In water; at 0 - 20℃;	Preparation 2.18-Methoxycinnolin-4(1H)-oneR3=8-OMe. (VI) A mixture of 2.0 g of the compound from Preparation 1.1 in 8 ml of concentrated HCl is cooled to 0 C., a solution of 1.25 g of NaNO2 in 2.7 ml of water is added dropwise while maintaining the temperature of the reaction mixture below 10 C. and the mixture is left stirring at 0 C. for 2 hours and at AT overnight. The reaction mixture is concentrated under vacuum, 50 ml of a sodium acetate solution are added and the precipitate formed is filtered off and washed with 20 ml of water. 1.95 g of the expected compound are obtained.

Reference： [1]Patent: US2011/144115,2011,A1 .Location in patent: Page/Page column 7

46
[ 15865-57-3 ]
[ 42465-54-3 ]

Reference： [1]Patent: US2011/144115,2011,A1
[2]Patent: US2012/129864,2012,A1
[3]Patent: WO2013/50527,2013,A1

47
[ 4920-80-3 ]
[ 42465-54-3 ]

Reference： [1]Patent: US2011/144115,2011,A1
[2]Patent: US2012/129864,2012,A1
[3]Patent: WO2013/50527,2013,A1

48
[ 42465-54-3 ]
[ 76-02-8 ]
[ 1429782-06-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; at 0 - 20℃; for 2h;	Synthesis of 2-chloro-8-methoxy-4-methyl-quinazoline 5d To a solution of the compound 5 (2.0g, 0.01 mol) in 30 mL of anhydrous CH2CI2 was added SOCI2 (4.4 ml, 0.062 mol) and DMF (0.2 mL), then themixture was stirred at 60C for 3 hours. The resulting mixture was concentratedin vacuum to give compound 5a (2.1 g, yield: 95.5%) as ayellow solid, which was used for next step without further purification.To a solution of Mg (0.26 g, 0.01 1mol) in 30 mL of anhydrous THF was added EtOH (0.4 g) and CCI4 (0.2 mL) at 50C. After being stirred for 30min, a solution of 1A (1 .76 g, 0.01 1 mol)and EtOH (0.65 g) in 10 mL of anhydrous THFwas added, the mixture was stirred at 60C for 2 hours. To this solution wasadded a solution of compound 5a (2.1 g, 0.01mol) in 10 mL of THF, the mixture wasstirred at 60C for 1 hour. The reaction mixture was cooled and quenched with 10 ml of aqueous H2SO4 (10%), the organic layers were concentrate in vacuum to give a yellow oil. To this oil was added a mixture of CH3COOH (15 mL), H2SO4 (2 mL) and H2O (10 mL),the mixture was stirred at reflux for 16 hours. The resulting mixture wasextracted with EtOAc (50 mL chi 3), the organic layers were concentrated toafford crude compound 5b (1 .4 g, yield: 73.7%). m/z = 196 [M + H]+ .To a solution of compound 5b (1 .2 g,6.15 mmol) in 20 mL of CH3COOH was addediron power (1 .0 g, 18.5 mmol), then the suspension was stirred at 70C for 4hours. The resulting mixture was filtered through apad of celite, the filtrate was neutralized with aqueous NaOH till pH = 7,extracted with EtOAc (50 mL x 3), the organic layers were concentrated toafford crude compound 5c (0.9 g, yield: 90%). m/z = 166 [M + H]+ .To a solution of the compound 5c(0.85 g, 5.15 mmol) in 20 mL of THF was added DMAP (0.69 g, 5.67 mmol) andCI3CCOCI (0.63 mL, 5.67 mmol) at 0C, then the mixture was stirred at roomtemperature for 2 hours. The resulting mixture was diluted with ice water (50mL), extracted with EtOAc (50 mL x 3), the organic layers were concentrated invacuum to give compound 5d (1 .2 g, yield: 76%), which was used for next stepwithout further purification. No MS signal.To a solution of the compound 5d (1.5 g, 4.8 mmol) in 20 mL of DMSO was added CH3COONH (1 .85 g, 24 mmol), the mixture was stirred at room temperaturefor 20 hours. The resulting mixture was diluted with H2O (200 mL), extracted with EtOAc (50 mL chi 3),the organic layers were concentrated in vacuum to give 8-methoxy-4-methyl-1H-quinazolin-2-one (0.6 g, yield: 65.2%), which was used for next step withoutfurther purification. 1H NMR (DMSO-c/e400 MHz TMS): 51 1 .0 (s, 1 H), 7.50 (q, J = 8.4 Hz, 1 H), 7.30 (d, J = 7.6 Hz,1 H), 7.15-7.19 (m, 1 H), 3.90 (s, 3 H), 2.67 (s, 3 H). m/z = 191 [M + H]+ .To a solution of the compound8-methoxy-4-methyl-1 H-quinazolin-2-one (200 mg, 1 .05 mmol) in 15 mL oftoluene was added POCI3 (0.2 mL, 2.1 mmol) and DIPEA (0.38 mL, 2.1 mmol), thenthe mixture was stirred at 90C for 4 hours. The resulting mixture wasconcentrated in vacuum, the residue was extracted with Et2O (50 mL), the organic layer was collected anddried to give 2-chloro-8-methoxy-4-methyl-quinazoline (100 mg, yield: 45.8%).m/z = 209 [M + H]+ .

Reference： [1]Patent: WO2013/50527,2013,A1 .Location in patent: Page/Page column 47; 48

49
[ 42465-54-3 ]
[ 953039-90-2 ]

Reference： [1]Patent: WO2013/50527,2013,A1
[2]Patent: WO2007/117607,2007,A2

50
[ 42465-54-3 ]
8-methoxy-4-methyl-1H-quinazolin-2-one [ No CAS ]

Reference： [1]Patent: WO2013/50527,2013,A1

51
[ 941-55-9 ]
[ 586-37-8 ]
[ 42465-54-3 ]
[ 23042-77-5 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 5225 - 5227

52
[ 42465-54-3 ]
[ 100-52-7 ]
8-methoxy-2-phenyl-2,3-dihydroquinolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With silver trifluoromethanesulfonate; In methanol; for 24h;Reflux; Inert atmosphere;	General procedure: AgOTf (26 mg, 10 mol%) was added to a solution of an o-aminoacetophenone (1.0 mmol) and an aryl aldehyde (1.2 mmol) in MeOH (5mL) at r.t. The reaction mixture was stirred under reflux for 12-24 h. After the reaction was complete, as indicated by TLC, the excess solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexanes-EtOAc, 20:1) to yield the desired product.

Reference： [1]Synthesis,2015,vol. 47,p. 3881 - 3890

53
[ 42465-54-3 ]
tert-butyl (8-methoxy-4-phenylquinolin-2-yl)carbonate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 4645 - 4653

54
[ 42465-54-3 ]
[ 100-58-3 ]
[ 859033-51-5 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 4645 - 4653

55
[ 14088-61-0 ]
[ 42465-54-3 ]
C₁₄H₁₅NO₂ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 6498 - 6501

56
[ 42465-54-3 ]
4-Methyl-6-(2-methoxy-5-pyridinyl)-8-(N-hydroxyacetamide-2-oxy)quinazoline [ No CAS ]