[ CAS No. 17329-31-6 ] {[proInfo.proName]}

Name: 17329-31-6|6-Aminoquinazolin-4(3H)-one|95%
Brand: Ambeed
SKU: A145794
Price: 17.0 USD
Availability: InStock
Rating: 91 (27 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 17329-31-6

Structure of 17329-31-6 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 17329-31-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17329-31-6 ]

SDS Specification

Alternatived Products of [ 17329-31-6 ]

Product Details of [ 17329-31-6 ]

CAS No. :	17329-31-6	MDL No. :	MFCD01219542
Formula :	C₈H₇N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MAIZCACENPZNCN-UHFFFAOYSA-N
M.W :	161.16	Pubchem ID :	135478037
Synonyms :

Calculated chemistry of [ 17329-31-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.77
TPSA :	71.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.72
Log Po/w (XLOGP3) :	0.09
Log Po/w (WLOGP) :	0.51
Log Po/w (MLOGP) :	0.54
Log Po/w (SILICOS-IT) :	1.36
Consensus Log Po/w :	0.65

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.51
Solubility :	4.95 mg/ml ; 0.0307 mol/l
Class :	Very soluble
Log S (Ali) :	-1.15
Solubility :	11.4 mg/ml ; 0.0705 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.22 mg/ml ; 0.00136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.51

Safety of [ 17329-31-6 ]

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 [ 17329-31-6 ]

* 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 [ 17329-31-6 ]
Downstream synthetic route of [ 17329-31-6 ]

[ 17329-31-6 ] Synthesis Path-Upstream 1~3

1
[ 6943-17-5 ]
[ 17329-31-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In methanol at 20℃; for 4 h;	Intermediate 5 [00201] In a 1 L flask was added Intermediate 5A (1 g, 5.23 mmol) in MeOH(500ml) to give a yellow suspension. 10percent Pd/C (0.056 g, 0.523 mmol) was added. The mixture was stirred at r.t. under a hydrogen balloon for 4 hours. The reaction mixture was filtered and concentrated to a yellow solid 0.84 g (100percent). ¹H NMR (500 MHz, DMSO-d₆) δ ppm 5.60 (s, 2 H) 7.05 (dd, J=8.80, 2.75 Hz, 1 H) 7.16 (d, J=2.75 Hz, 1 H) 7.36 (d, J=8.80 Hz, 1 H) 7.74 (s, 1 H) 11.80 (s, 1 H).
100%	With hydrogen In methanol at 20℃; for 4 h;	Intermediate 4; [00201] In a 1 L flask was added Intermediate 4A (1 g, 5.23 mmol) in MeOH(500 mL) to give a yellow suspension. 10percent Pd/C (0.056 g, 0.523 mmol) was added. The mixture was stirred at rt under a hydrogen balloon for 4 h. The reaction mixture was filtered and concentrated to a yellow solid 0.84 g (100percent). ¹H NMR (500 MHz, DMSO-d₆) δ ppm 5.60 (s, 2 H) 7.05 (dd, J=8.80, 2.75 Hz, 1 H) 7.16 (d, J=2.75 Hz, 1 H) 7.36 (d, J=8.80 Hz, 1 H) 7.74 (s, 1 H) 11.80 (s, 1 H).
73%	With stannous chloride dihydrate In ethyl acetate for 8 h; Reflux	General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 °C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO₄ and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO₄ and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl₂*2H₂O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 .x. 50 mL). The organic layers were combined, dried over anhydrous MgSO₄ and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 .x. 10 mL), the organic extracts were combined, dried over MgSO₄ and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.

30%

With tin(II) chloride dihdyrate In methanol for 3 h; Reflux; Inert atmosphere

A mixture of 1 g (5 mmol) of 6-nitroquinazolin-4-(3H)-one 11 and 6 g (25 mmol) of SnCl₂·2H₂O in 25 mL methanol was heated to reflux for 3 h while stirring under argon. The solvent was evaporated then 200 mL saturated aqueous NaHCO₃ solution were added to the residue and left stirring for 10 min. The suspension was then filtered and the aqueous filtrate was collected and evaporated. The product was then extracted from the residue using DMF and purified using column chromatography (90percent DCM, 10percent 0.5 M NH₃ in methanol solution) to give the pure compound 12. Yield: 30percent; mp: 310–312 °C; ¹H-NMR (200 MHz, DMSO-d₆) δ: 11.80 (s, 1H), 7.74 (s, 1H), 7.36 (d, J=8.6 Hz, 1H), 7.17 (d, J=2.2 Hz, 1H), 7.05 (dd, J=8.7,2.4 Hz, 1H), 5.59 (s, 2H); ¹³C-NMR (50 MHz, DMSO-d₆) δ: 161.03, 148.20, 140.63, 139.97, 128.38, 123.99, 122.49, 106.48; MS (ESI): m/z=161.9 (M+H)⁺.

Reference： [1] Patent: WO2008/79759, 2008, A1, . Location in patent: Page/Page column 90
[2] Patent: WO2008/79836, 2008, A2, . Location in patent: Page/Page column 86
[3] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4455 - 4458
[4] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[5] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 12, p. 1166 - 1172
[6] Yakugaku Zasshi, 1942, vol. 62, p. 66,68; dtsch. Ref. S. 24[7] Chem.Abstr., 1951, p. 1580
[8] Yakugaku Zasshi, 1942, vol. 62, p. 66,68; dtsch. Ref. S. 24[9] Chem.Abstr., 1951, p. 1580
[10] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[11] Patent: WO2006/12374, 2006, A1, . Location in patent: Page/Page column 181
[12] Patent: US6339099, 2002, B1, . Location in patent: Page column 43, 44
[13] Patent: US2003/225106, 2003, A1, . Location in patent: Page 86
[14] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 11, p. 3235 - 3239

2
[ 616-79-5 ]
[ 17329-31-6 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4455 - 4458
[2] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273

3
[ 17420-30-3 ]
[ 17329-31-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 12, p. 1166 - 1172

[ 17329-31-6 ] Synthesis Path-Downstream 1~33

1
[ 6943-17-5 ]
[ 17329-31-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 4h;	Intermediate 5 [00201] In a 1 L flask was added Intermediate 5A (1 g, 5.23 mmol) in MeOH(500ml) to give a yellow suspension. 10% Pd/C (0.056 g, 0.523 mmol) was added. The mixture was stirred at r.t. under a hydrogen balloon for 4 hours. The reaction mixture was filtered and concentrated to a yellow solid 0.84 g (100%). 1H NMR (500 MHz, DMSO-d6) delta ppm 5.60 (s, 2 H) 7.05 (dd, J=8.80, 2.75 Hz, 1 H) 7.16 (d, J=2.75 Hz, 1 H) 7.36 (d, J=8.80 Hz, 1 H) 7.74 (s, 1 H) 11.80 (s, 1 H).
100%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 4h;	Intermediate 4; [00201] In a 1 L flask was added Intermediate 4A (1 g, 5.23 mmol) in MeOH(500 mL) to give a yellow suspension. 10% Pd/C (0.056 g, 0.523 mmol) was added. The mixture was stirred at rt under a hydrogen balloon for 4 h. The reaction mixture was filtered and concentrated to a yellow solid 0.84 g (100%). 1H NMR (500 MHz, DMSO-d6) delta ppm 5.60 (s, 2 H) 7.05 (dd, J=8.80, 2.75 Hz, 1 H) 7.16 (d, J=2.75 Hz, 1 H) 7.36 (d, J=8.80 Hz, 1 H) 7.74 (s, 1 H) 11.80 (s, 1 H).
73%	With stannous chloride dihydrate; In ethyl acetate; for 8h;Reflux;	General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2·2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 × 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 × 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.

30%	With tin(II) chloride dihdyrate; In methanol; for 3h;Reflux; Inert atmosphere;	A mixture of 1 g (5 mmol) of 6-nitroquinazolin-4-(3H)-one 11 and 6 g (25 mmol) of SnCl2·2H2O in 25 mL methanol was heated to reflux for 3 h while stirring under argon. The solvent was evaporated then 200 mL saturated aqueous NaHCO3 solution were added to the residue and left stirring for 10 min. The suspension was then filtered and the aqueous filtrate was collected and evaporated. The product was then extracted from the residue using DMF and purified using column chromatography (90% DCM, 10% 0.5 M NH3 in methanol solution) to give the pure compound 12. Yield: 30%; mp: 310-312 C; 1H-NMR (200 MHz, DMSO-d6) delta: 11.80 (s, 1H), 7.74 (s, 1H), 7.36 (d, J=8.6 Hz, 1H), 7.17 (d, J=2.2 Hz, 1H), 7.05 (dd, J=8.7,2.4 Hz, 1H), 5.59 (s, 2H); 13C-NMR (50 MHz, DMSO-d6) delta: 161.03, 148.20, 140.63, 139.97, 128.38, 123.99, 122.49, 106.48; MS (ESI): m/z=161.9 (M+H)+.
	With hydrogen;palladium 10% on activated carbon; In ethanol; for 1h;	Hydrogenation of 6-nitro-3H-quinazolin-4-one (2 g) in EtOH(200 mL) was catalyzed by Pd/c (10%, 200 mg) under a H2balloon for 1 h. MeOH (200 mL) was added to the mixture.The suspension was filtered through a layer of Celite andthe filtrate was concentrated in vacuum to give the desiredcompound.
	With hydrogen;palladium 10% on activated carbon; In ethanol; for 1h;	Hydrogenation of 6-nitro-3H-quinazolin-4-one (2 g) in EtOH (200 mL) was catalyzed by Pd/C (10%, 200 mg) under a H2 balloon for 1 h. MeOH (200 mL) was added to the mixture. The suspension was filtered through a layer of Celite and the filtrate was concentrated in vacuum to give the desired compound.

Reference： [1]Patent: WO2008/79759,2008,A1 .Location in patent: Page/Page column 90
[2]Patent: WO2008/79836,2008,A2 .Location in patent: Page/Page column 86
[3]Tetrahedron Letters,2003,vol. 44,p. 4455 - 4458
[4]European Journal of Medicinal Chemistry,2012,vol. 50,p. 264 - 273
[5]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 1166 - 1172
[6]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1942,vol. 62,p. 66,68; dtsch. Ref. S. 24
Chem.Abstr.,1951,p. 1580
[7]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1942,vol. 62,p. 66,68; dtsch. Ref. S. 24
Chem.Abstr.,1951,p. 1580
[8]Journal of Organic Chemistry,1952,vol. 17,p. 149,153
[9]Patent: WO2006/12374,2006,A1 .Location in patent: Page/Page column 181
[10]Patent: US6339099,2002,B1 .Location in patent: Page column 43, 44
[11]Patent: US2003/225106,2003,A1 .Location in patent: Page 86
[12]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3235 - 3239

3
6-nitro-quinazolone-⁽⁴⁾ [ No CAS ]
[ 17329-31-6 ]

Reference： [1]Journal of the American Chemical Society,1912,vol. 34,p. 532

4
[ 17329-31-6 ]
4,5-dichloro-1,2,3-dithiazolium chloride [ No CAS ]
6-(4-chloro-[1,2,3]dithiazol-5-ylideneamino)-3<i>H</i>-quinazolin-4-one [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4455 - 4458

5
[ 17329-31-6 ]
2-nitrilo-<i>N</i>-(4-oxo-3,4-dihydro-quinazolin-6-yl)-acetimidoyl chloride [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4455 - 4458

6
[ 616-79-5 ]
[ 17329-31-6 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4455 - 4458
[2]European Journal of Medicinal Chemistry,2012,vol. 50,p. 264 - 273
[3]Russian Journal of General Chemistry,2020,vol. 90,p. 720 - 724

7
[ 4693-02-1 ]
[ 17329-31-6 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 852 - 856

8
[ 17329-31-6 ]
[ 93-02-7 ]
6-(2,5-Dimethoxybenzylamino)-3H-quinazolin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; In methanol;	EXAMPLE 21 6-(2,5-Dimethoxybenzylamino)-3H-quinazolin-4-one (Process a) A mixture of 200 mg of <strong>[17329-31-6]6-amino-3H-quinazolin-4-one</strong> and 206 mg of 2,5-dimethoxybenzaldehyde in 12 ml of dry methanol is heated to 60 for 16 hours. cooling the yellow precipitate is filtered and resuspended in 10 ml of dry methanol. This mixture is treated with 85 mg of sodium cyanoborohydride and heated for some minutes until all the materials are dissolved. After stirring for 2 at room temperature, the mixture is poured into water and extracted with acetate. The combined organic extracts are dried over magnesium sulfate and evaporated in vacuo. The pure title compound is obtained by crystallisation from ethanol as colourless crystals. mp: 203-205.

Reference： [1]Patent: US5990116,1999,A

9
[ 17329-31-6 ]
[ 122775-35-3 ]
[ 298-12-4 ]
[ 1036390-09-6 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; acetonitrile; at 60.0℃;	In a 25 mL flask was added glyoxylic acid monohydrate (38.4 mg,0.417 mmol), Intermediate 5 (56 mg, 0.347 mmol), and 3,4- dimethoxybenzeneboronic acid (76 mg, 0.417 mmol) in MeCN (1.1 ml)/DMF(0.122 mL) to give a brown suspension. The reaction was stirred at 60 0C overnight. Solvent was removed and the crude residue was dissolved in a small amount of acetonitrile/ water and purified by prep HPLC using AXIA column ( 2 injections) eluted with 90% water to 10% water in acetonitrile with 0.1% TFA. 23A (50 mg) was obtained as a solid. 1H NMR (400 MHz, CDCl3) delta ppm 3.81 (s, 3 H) 3.83 (s, 3 H) 5.14 (s, 1 H) 6.94 (d, J=8.35 Hz, 1 H) 7.10 (dd, J=8.35, 2.20 Hz, 1 H) 7.15 (d, J=I.76 Hz, 1 H) 7.24 (d, J=2.64 Hz, 1 H) 7.37 (dd, J=9.01, 2.86 Hz, 1 H) 7.47 - 7.51 (m, 1 H) 8.47 (s, 1 H). LCMS 356 (M+H).

Reference： [1]Patent: WO2008/79759,2008,A1 .Location in patent: Page/Page column 147
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1077 - 1081

10
[ 17329-31-6 ]
[ 103-80-0 ]
[ 1233719-49-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3235 - 3239

11
[ 17329-31-6 ]
[ 388082-78-8 ]

Reference： [1]Patent: WO2014/170910,2014,A1

12
[ 17329-31-6 ]
[ 98-88-4 ]
N-(4-oxo-3,4-dihydroquinazolin-6-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium hydrogencarbonate; In acetone; for 3.0h;	To a mixture of 1 mmol of <strong>[17329-31-6]6-aminoquinazolin-4-(3H)-one</strong> 12 and 1.1 mmol of NaHCO3, 15 mL acetone were added. Then, 1.1 mmol of benzoyl chloride was dissolved in 1.5 mL acetone and was added drop wise to the previously prepared mixture while stirring in an ice bath. The reaction mixture was stirred for 3 h at 0 C. The mixture was then poured on a saturated solution of NaHCO3 to form a precipitate which was separated by filtration and purified using column chromatography to give compound 13. Yield: 47%; mp: 322-323 C; 1H-NMR (400 MHz, DMSO-d6) delta: 12.20 (s, 1H), 10.59 (s, 1H), 8.66 (s, 1H), 8.19 (d, J=8.8 Hz, 1H), 8.02 (d, J=9.0 Hz, 2H), 7.99 (s, 1H), 7.68 (d, J=8.8 Hz, 1H), 7.58 (dt, J=25.3, 7.1 Hz, 3H); 13C-NMR (101 MHz, DMSO-d6) delta: 165.70, 160.60, 144.93, 144.07, 137.69, 134.56, 131.74, 128.41, 127.69, 127.65, 127.00, 122.83, 115.64; HR-MS (ESI-TOF-HR): (M+Na)+=288.07449 (Calcd for 288.07435); purity (HPLC): 99.9%.

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 1166 - 1172

13
[ 17420-30-3 ]
[ 17329-31-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 1166 - 1172

14
[ 17329-31-6 ]
10-hydroxy-1H,2H,7H,10H-pyrido[3,2-f]quinazolin-1-one [ No CAS ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 8230 - 8240

15
[ 17329-31-6 ]
2-[2-(diethylamino)ethyl]-10-hydroxy-1H,2H,7H,10H-pyrido[3,2-f]quinazolin-1-one hydrochloride [ No CAS ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 8230 - 8240

16
[ 17329-31-6 ]
C₁₇H₂₀N₄O₂ [ No CAS ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 8230 - 8240

17
[ 2033-24-1 ]
[ 17329-31-6 ]
[ 149-73-5 ]
6,6-dimethyl-3-[(4-oxo-3,4-dihydroquinazolin-6-yl)amino]methylidene}oxane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.8%		A solution of Meldrum's acid (1.427 g, 9.91 mmol) in an excess of methyl orthoformate (15 mL) was heated to reflux for two hours under nitrogen atmosphere. The solution was then cooled to room temperature and the starting 6-aminoquinazolinone (13, 1.228 g,7.62 mmol) was added portion wise. The mixture thus obtained was maintained at reflux for 6 h, checking the progress of the reaction by TLC (eluent CHCl3/MeOH, 8:2). The reaction mixture was partly evaporated in a rotavapor, then taken up with water and subsequently extracted with EtOAc. The combined extracts were dried with anhydrous sodium sulfate, filtered and then evaporated to dryness. The crude reaction residue was purified by silica gel column chromatography (eluent CHCl3/MeOH, 8:2) and additionally re-crystallized from MeOH yielding 2.063 g (6.54 mmol) of a yellow powdery solid. Yield: 85.8%; mp: 247 C; Rf 0.52 (CHCl3/MeOH,8:2); nmax (ATR, ZnSe) 3421-3108, 1750, 1740, 1675, 1415, 1400, 1112,987 cm1;dH NMR (400 MHz, DMSO-d6) 1.69 (s, 6H, C(CH3)2), 7.72(d, J 8.83, 1H, H-8), 8.04 (dd, J 8.83 Hz and J 2.70 Hz, 1H, H-7), 8.09(d, J 3.26 Hz, 1H, H-2), 8.19 (d, J 2.63 Hz, 1H, H-5), 8.62 (d, J 14.74 Hz,1H, CHNH), 11.40 (d, J 14.46 Hz, 1H, CHNH), 12.34 ppm (bs, 1H,CONH); dC NMR (101 MHz, DMSO-d6) 26.86 (C(CH3)2), 87.72(CHNH), 104.54 (C(CH3)2), 115.54 (C-5), 123.63 (C-4a), 126.39 (C-7),129.05 (C-8),145.83 (C-2), 147.10 (C-8a),159.92 (C-4),163.15 (C]O),163.96 (C]O),167.65 (C-4),197.58 ppm (C]CH); HRMS (ESI-MS,140 eV): m/z [M H] C15H14N3O5 requires 316.0933; found, 316.0930.

Reference： [1]Tetrahedron,2016,vol. 72,p. 8230 - 8240

18
[ 17329-31-6 ]
[ 122775-35-3 ]
methyl 3-(1-(2-(3,4-dimethoxyphenyl)-2-(4-oxo-3,4-dihydroquinazolin-6-ylamino)acetyl)pyrrolidin-2-yl)-4-(isopropylsulfonyl)phenylcarbamate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1077 - 1081

19
[ 91-56-5 ]
[ 17329-31-6 ]