Name: 54166-95-9|6-Chloro-2-aminobenzamide|97%
Brand: Ambeed
SKU: A801692
Price: 37.0 USD
Availability: InStock
Rating: 95 (30 reviews)

1
[ 54166-95-9 ]
[ 4755-77-5 ]
[ 54166-68-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine
		37 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25. EXAMPLE 37 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25. 2-Amino-6-chlorobenzamide (4.26 g, 0.025 mole) is condensed with 3.1 ml (0.0275 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 5.28 g of the title compound, m.p. 190°-193° C., after crystallization from ethanol. Elemental Analysis for C11 H11 CIN2 O4: Calc'd: C, 48.8; H, 4.10; N, 10.35. Found: C, 49.08; H, 4.05; N, 10.72.
		20 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25 EXAMPLE 20 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25 2-Amino-6-chlorobenzamide (4.26 g., 0.025 mole) is condensed with 3.1 ml. (0.0275 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 5.28 g. of the title compound, m.p. 190°-193° C., after crystallization from ethanol. Elemental Analysis for C11 H11 CLN2 O4: Calc'd: C, 48.8; H, 4.10; N, 10.35. Found: C, 49.08; H, 4.05; N, 10.72.

		20 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25 EXAMPLE 20 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25 2-Amino-6-chlorobenzamide (4.26 g., 0.025 mole) is condensed with 3.1 ml. (0.0275 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 5.28 g. of the title compound, m.p. 190°-193° C., after crystallization from ethanol. Elemental Analysis for C11 H11 CLN2 O4: Calc'd: C, 48.8; H, 4.10; N, 10.35: Found: C, 49.08; H, 4.05; N, 10.72.
		20 2'-Carbamyl-3'-chlorooxanilic acid ethyl ester. 25. EXAMPLE 20 2'-Carbamyl-3'-chlorooxanilic acid ethyl ester. 25. 2-Amino-6-chlorobenzamide (4.26 g., 0.025 mole) is condensed with 3.1 ml. (0.0275 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 5.28 g. of the title compound, m.p. 190°-193° C., after crystallization from ethanol. Elemental Analysis for C11 H11 ClN2 O4: Calc'd: C, 48.8; H, 4.10; N, 10.35. Found: C, 49.08; H, 4.05; N, 10.72.
		37 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25 EXAMPLE 37 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25 2-Amino-6-chlorobenzamide (4.26 g, 0.025 mole) is condensed with 3.1 ml (0.0275 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 5.28 g of the title compound, m.p. 190°-193° C., after crystallization from ethanol. Elemental Analysis for C11 H11 CIN2 O4: Calc'd: C, 48.8; H, 4.10; N, 10.35. Found: C, 49.08; H, 4.05; N, 10.72.
		37 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25 EXAMPLE 37 2'-Carbamoyl-3'-chlorooxanilic acid ethyl ester. 25 2-Amino-6-chlorobenzamide (4.26 g, 0.025 mole) is condensed with 3.1 ml (0.0275 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 5.28 g of the title compound, m.p. 190°-193°C., after crystallization from ethanol. Elemental Analysis for C11 H11 CIN2 O4: Calc'd: C, 48.8; H, 4.10; N, 10.35. Found: C, 49.08; H, 4.05; N, 10.72.

Reference： [1]Sellstedt; Guinosso; Begany; Bell; Rosenthale [Journal of Medicinal Chemistry, 1975, vol. 18, # 9, p. 926 - 933]
[2]Current Patent Assignee: PFIZER INC - US4054661, 1977, A
[3]Current Patent Assignee: PFIZER INC - US4069343, 1978, A
[4]Current Patent Assignee: PFIZER INC - US4191840, 1980, A
[5]Current Patent Assignee: PFIZER INC - US4154961, 1979, A
[6]Current Patent Assignee: PFIZER INC - US4160100, 1979, A
[7]Current Patent Assignee: PFIZER INC - US3966965, 1976, A

2
[ 54166-95-9 ]
[ 14301-31-6 ]
2-Chloro-6-([2-(3,4-dimethoxy-phenyl)-ethylcarbamoyl]-methyl}-amino)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	at 160℃; for 5h;

Reference： [1]Hosokami; Kuretani; Higashi; Asano; Ohya; Takasugi; Mafune; Miki [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 10, p. 2712 - 2719]

3
[ 54166-95-9 ]
[ 29671-92-9 ]
[ 50440-85-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With dimethylsulfone at 160℃; for 1h;

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C. [Journal of Organic Chemistry, 1986, vol. 51, # 21, p. 4067 - 4070]

4
[ 63904-41-6 ]
[ 54166-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In methanol Yield given;

Reference： [1]Eger [Archiv der Pharmazie, 1981, vol. 314, # 2, p. 176 - 180]

5
[ 54166-95-9 ]
[ 57-13-6 ]
[ 78754-81-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 653 - 654
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 2247 - 2254

Yield	Reaction Conditions	Operation in experiment
	2-Chlor-6-nitro-benzonitril, Bzl., W., Fe;

7
[ 927-58-2 ]
[ 54166-95-9 ]
2-(4-bromo-butyrylamino)-6-chloro-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In dichloromethane at 0℃; for 1.5h;

Reference： [1]Hattori, Kouji; Kido, Yoshiyuki; Yamamoto, Hirofumi; Ishida, Junya; Kamijo, Kazunori; Murano, Kenji; Ohkubo, Mitsuru; Kinoshita, Takayoshi; Iwashita, Akinori; Mihara, Kayoko; Yamazaki, Syunji; Matsuoka, Nobuya; Teramura, Yoshinori; Miyake, Hiroshi [Journal of Medicinal Chemistry, 2004, vol. 47, # 17, p. 4151 - 4154] Ishida, Junya; Yamamoto, Hirofumi; Kido, Yoshiyuki; Kamijo, Kazunori; Murano, Kenji; Miyake, Hiroshi; Ohkubo, Mitsuru; Kinoshita, Takayoshi; Warizaya, Masaichi; Iwashita, Akinori; Mihara, Kayoko; Matsuoka, Nobuya; Hattori, Kouji [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 5, p. 1378 - 1390]

8
[ 54166-95-9 ]
5-chloro-2-[3-(4-phenyl-3,6-dihydro-1(2H)-pyridinyl)propyl]-4(3H)-quinazolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine / CH₂Cl₂ / 1.5 h / 0 °C 2: dimethylformamide / 24 h / 20 °C 3: sodium hydroxide / dioxane; H₂O / 15 h / 20 °C
	Multi-step reaction with 3 steps 1: pyridine / CH₂Cl₂ / 1.5 h / 0 °C 2: Et₃N / dimethylformamide / 24 h / 20 °C 3: aq. NaOH / dioxane / 15 h / 20 °C

Reference： [1]Ishida, Junya; Yamamoto, Hirofumi; Kido, Yoshiyuki; Kamijo, Kazunori; Murano, Kenji; Miyake, Hiroshi; Ohkubo, Mitsuru; Kinoshita, Takayoshi; Warizaya, Masaichi; Iwashita, Akinori; Mihara, Kayoko; Matsuoka, Nobuya; Hattori, Kouji [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 5, p. 1378 - 1390]
[2]Hattori, Kouji; Kido, Yoshiyuki; Yamamoto, Hirofumi; Ishida, Junya; Kamijo, Kazunori; Murano, Kenji; Ohkubo, Mitsuru; Kinoshita, Takayoshi; Iwashita, Akinori; Mihara, Kayoko; Yamazaki, Syunji; Matsuoka, Nobuya; Teramura, Yoshinori; Miyake, Hiroshi [Journal of Medicinal Chemistry, 2004, vol. 47, # 17, p. 4151 - 4154]

9
[ 54166-95-9 ]
2-chloro-6-[4-(4-phenyl-3,6-dihydro-2<i>H</i>-pyridin-1-yl)-butyrylamino]-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / CH₂Cl₂ / 1.5 h / 0 °C 2: dimethylformamide / 24 h / 20 °C
	Multi-step reaction with 2 steps 1: pyridine / CH₂Cl₂ / 1.5 h / 0 °C 2: Et₃N / dimethylformamide / 24 h / 20 °C

Reference： [1]Ishida, Junya; Yamamoto, Hirofumi; Kido, Yoshiyuki; Kamijo, Kazunori; Murano, Kenji; Miyake, Hiroshi; Ohkubo, Mitsuru; Kinoshita, Takayoshi; Warizaya, Masaichi; Iwashita, Akinori; Mihara, Kayoko; Matsuoka, Nobuya; Hattori, Kouji [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 5, p. 1378 - 1390]
[2]Hattori, Kouji; Kido, Yoshiyuki; Yamamoto, Hirofumi; Ishida, Junya; Kamijo, Kazunori; Murano, Kenji; Ohkubo, Mitsuru; Kinoshita, Takayoshi; Iwashita, Akinori; Mihara, Kayoko; Yamazaki, Syunji; Matsuoka, Nobuya; Teramura, Yoshinori; Miyake, Hiroshi [Journal of Medicinal Chemistry, 2004, vol. 47, # 17, p. 4151 - 4154]

10
[ 54166-95-9 ]
[ 78754-83-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 84 percent / NH₃ / butan-1-ol / 24 h / 120 - 130 °C
	Multi-step reaction with 3 steps 1: 78 percent / fusion 2: 97 percent / fumic HNO₃, conc. H₂SO₄ / 1.) -10 deg C; 2.) warming 3: 84 percent / NH₃ / butan-1-ol / 24 h / 140 - 150 °C / sealed vessel

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]
[2]Schneller, Stewart W.; Christ, William J. [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 653 - 654]

11
[ 54166-95-9 ]
[ 78754-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min
	Multi-step reaction with 2 steps 1: 78 percent / fusion 2: 97 percent / fumic HNO₃, conc. H₂SO₄ / 1.) -10 deg C; 2.) warming

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]
[2]Schneller, Stewart W.; Christ, William J. [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 653 - 654]

12
[ 54166-95-9 ]
[ 78754-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 67 percent / 20percent aq. tetraethylammnium hydroxide / H₂O / 30 - 35 °C
	Multi-step reaction with 3 steps 1: 78 percent / fusion 2: 97 percent / fumic HNO₃, conc. H₂SO₄ / 1.) -10 deg C; 2.) warming 3: 67 percent / tetraethylammonium hydroxide / 30 - 35 °C

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]
[2]Schneller, Stewart W.; Christ, William J. [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 653 - 654]

13
[ 54166-95-9 ]
[ 78754-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 67 percent / 20percent aq. tetraethylammnium hydroxide / H₂O / 30 - 35 °C 4: 91 percent / NH₃ / butan-1-ol / 2 h / 125 °C
	Multi-step reaction with 4 steps 1: 78 percent / fusion 2: 97 percent / fumic HNO₃, conc. H₂SO₄ / 1.) -10 deg C; 2.) warming 3: 67 percent / tetraethylammonium hydroxide / 30 - 35 °C 4: 91 percent / NH₃ / butan-1-ol / 24 h / 130 - 140 °C / sealed vessel

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]
[2]Schneller, Stewart W.; Christ, William J. [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 653 - 654]

14
[ 54166-95-9 ]
[ 78754-87-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 67 percent / 20percent aq. tetraethylammnium hydroxide / H₂O / 30 - 35 °C 4: 89 percent / butan-1-ol / 24 h / 140 °C
	Multi-step reaction with 4 steps 1: 78 percent / fusion 2: 97 percent / fumic HNO₃, conc. H₂SO₄ / 1.) -10 deg C; 2.) warming 3: 67 percent / tetraethylammonium hydroxide / 30 - 35 °C 4: 89 percent / butan-1-ol / 24 h / 140 - 150 °C / sealed vessel

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]
[2]Schneller, Stewart W.; Christ, William J. [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 653 - 654]

15
[ 54166-95-9 ]
[ 121496-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 84 percent / NH₃ / butan-1-ol / 24 h / 120 - 130 °C 4: 52 percent / K₂CO₃ / dimethylformamide / 6 h / 60 °C

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]

16
[ 54166-95-9 ]
[ 121496-97-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 67 percent / 20percent aq. tetraethylammnium hydroxide / H₂O / 30 - 35 °C 4: 91 percent / NH₃ / butan-1-ol / 2 h / 125 °C 5: 1)conc. HCl, H₂, 2) pyridine / 1) 10percent Pd-C / 1) EtOH, 52 psi, 12 h, 2) reflux, 1 h

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]

17
[ 54166-95-9 ]
[ 121496-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 84 percent / NH₃ / butan-1-ol / 24 h / 120 - 130 °C 4: 40 percent / K₂CO₃ / dimethylformamide / 6 h / 60 °C

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]

18
[ 54166-95-9 ]
[ 121496-98-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 84 percent / NH₃ / butan-1-ol / 24 h / 120 - 130 °C 4: 52 percent / K₂CO₃ / dimethylformamide / 6 h / 60 °C 5: 1)conc. HCl, H₂, 2) pyridine / 1) 10percent Pd-C / 1) EtOH, 52 psi, 12 h, 2) reflux, 1 h

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]

19
[ 54166-95-9 ]
[ 121496-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / 1.5 h / 190 °C 2: 97 percent / fuming HNO₃, conc. H₂SO₄ / -10 deg C, then to room temperature, then heating, 10 min 3: 84 percent / NH₃ / butan-1-ol / 24 h / 120 - 130 °C 4: 81 percent / K₂CO₃ / dimethylformamide / 6 h / 60 °C

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C.; Christ, William J.; Bruns, Robert F. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2247 - 2254]

20
[ 28144-70-9 ]
[ 54166-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / SCl₂ 2: SCl₂ / Heating 3: aq. NaOH / methanol

Reference： [1]Eger [Archiv der Pharmazie, 1981, vol. 314, # 2, p. 176 - 180]

21
[ 33800-08-7 ]
[ 54166-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SCl₂ / Heating 2: aq. NaOH / methanol

Reference： [1]Eger [Archiv der Pharmazie, 1981, vol. 314, # 2, p. 176 - 180]

22
[ 54166-95-9 ]
[ 103884-20-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / Me₂SO₂ / 1 h / 160 °C 2: 100 percent / conc. H₂SO₄, fuming HNO₃ / 1.) a) from -10 to RT, b) reflux, 10 min 3: 98 percent / NH₃ / butan-1-ol / 24 h / 180 °C

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C. [Journal of Organic Chemistry, 1986, vol. 51, # 21, p. 4067 - 4070]

23
[ 54166-95-9 ]
[ 103884-19-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / Me₂SO₂ / 1 h / 160 °C 2: 100 percent / conc. H₂SO₄, fuming HNO₃ / 1.) a) from -10 to RT, b) reflux, 10 min

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C. [Journal of Organic Chemistry, 1986, vol. 51, # 21, p. 4067 - 4070]

24
[ 54166-95-9 ]
[ 103884-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / Me₂SO₂ / 1 h / 160 °C 2: 100 percent / conc. H₂SO₄, fuming HNO₃ / 1.) a) from -10 to RT, b) reflux, 10 min 3: 100 percent / butan-1-ol / 24 h / 130 °C

Reference： [1]Schneller, Stewart W.; Ibay, Augusto C. [Journal of Organic Chemistry, 1986, vol. 51, # 21, p. 4067 - 4070]

25
[ 54166-95-9 ]
[ 78754-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / fusion 2: 97 percent / fumic HNO₃, conc. H₂SO₄ / 1.) -10 deg C; 2.) warming 3: 84 percent / NH₃ / butan-1-ol / 24 h / 140 - 150 °C / sealed vessel 4: 1.) H₂, conc. HCl / 1.) 10percent Pd on charcoal / 1.) 2-methoxyethanol; 2.) room temperature

Reference： [1]Schneller, Stewart W.; Christ, William J. [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 653 - 654]

26
[ 41731-23-1 ]
[ 54166-95-9 ]
6-chloro-2-methyl-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 12 2-methyl-6-chloro-5H-thiazolo-(2,3-b)-quinazolin-5-one (compound 14) 10.2 g of 6-chloroanthranilamide and 10.74 g of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> were stirred at 140 C. for 2 hours. After working up in the conventional manner there was obtained 11.7 g (78%) of the above compound; m.p. 235-236 C.

Reference： [1]Patent: US5030727,1991,A

27
[ 6575-11-7 ]
[ 54166-95-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With water; potassium carbonate; In water; at 150℃; for 0.5h;Microwave irradiation;	General procedure: Adapted from a literature procedure,1 the appropriate organonitrile (1.0 eq.) and K2CO3(0.2eq.)wereaddedtoamicrowavetubewithastir-barwithdeionizedwater(8.5mLpermmolsubstrate).Afterirradiationundermicrowaveat150Cfor30minutes,thereactionmixturewascooled,extractedwithEtOAc(320mL),thecombinedphasesdriedoverMgSO4andexcesssolventremovedinvacuo.TheresiduewaspurifiedbyFCC,ifrequired,togivethetitlecompound.
79%	With water extract of pomelo, peel; at 150℃; for 0.5h;Sealed tube; Green chemistry;	General procedure: Benzonitrile 1a (103 mg, 1.0 mmol) and WEPPA (2.0 mL) were added into a 10-mL closed tubewith a stir bar. Then the reaction was stirred in a closed vessel synthesis reactor at 150 C for 0.5 h.After cooling to ambient temperature, the resulting precipitate was collected by filtration, washed withice water, and further dried in a vacuum drying oven. The filtrate was evaporated under reducedpressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleumether (35-60 C)/EtOAc = 2:1 to 0:1, v/v). Finally, these two parts were combined to produce the desiredbenzamide 2a with a 94% yield.

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 5095 - 5101
[2]Synthesis,2017,vol. 49,p. 135 - 144
[3]Green Chemistry,2012,vol. 14,p. 921 - 924
[4]Journal of the American Chemical Society,2008,vol. 130,p. 15786 - 15787
[5]Molecules,2019,vol. 24

28
[ 54166-95-9 ]
[ 590-86-3 ]
[ 1086673-24-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With C₇₂H₆₁O₄P In toluene at -45℃; for 24h; Inert atmosphere; Molecular sieve; optical yield given as %ee; enantioselective reaction;

Reference： [1]Cheng, Xu; Vellalath, Sreekumar; Goddard, Richard; List, Benjamin [Journal of the American Chemical Society, 2008, vol. 130, # 47, p. 15786 - 15787]

29
[ 5390-04-5 ]
[ 54166-95-9 ]
[ 1208003-36-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With platinum(II) bromde In methanol at 80℃; for 12h; Inert atmosphere;

Reference： [1]Patil, Nitin T.; Kavthe, Rahul D.; Raut, Vivek S.; Shinde, Valmik S.; Sridhar, Balasubramanian [Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1277 - 1280]

30
[ 54166-95-9 ]
[ 536-74-3 ]
[ 1246861-70-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In toluene at 100℃; for 24h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Patil, Nitin T.; Lakshmi, Pediredla G.V.V.; Singh, Vipender [European Journal of Organic Chemistry, 2010, # 24, p. 4719 - 4731]

31
[ 20829-96-3 ]
[ 54166-95-9 ]

Yield	Reaction Conditions	Operation in experiment
49%	With ethanol; ammonia; at 20℃; for 2h;	Example 32. Preparation of 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethyIphenyl)quinazolin-4(3H)-one [0266] A mixture of <strong>[20829-96-3]2-amino-6-chlorobenzoic acid</strong> (5.00 g, 29.1 mmol) in acetonitrile (50.0 ml_) was stirred at room temperature under nitrogen. Pyridine (4.72 mL, 58.3 mmol) was added, followed by drop-wise addition of triphosgene (2.85 g, 9.60 mmol) in CH2CI2 (20.0 mL). After the addition, the mixture was heated at 55C for 2 hours, then cooled to 25C and stirred overnight. Water (100 mL) was added to quench, the mixture was filtered, and washed with cold CH2CI2, to provide 5-chloro-1/-/-benzo[d][1 ,3]oxazine-2,4-dione (3.54 g, 62%) as a white solid.[0267] A mixture of <strong>[20829-96-3]5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione</strong> (3.50 g, 17.7 mmol) and 2 M NH3 in EtOH (11.5 mL, 23.0 mmol) and EtOH (10.0 mL) was stirred at room temperature for 2 hours. The volatiles were removed under reduced pressure, the residue was triturated with water (50 mL), and the solid was filtered, to provide 2-amino-6-chlorobenzamide (1.60 g, 49%) as a tan solid.[0268] A mixture of 2-amino-6-chlorobenzamide (0.490 g, 3.00 mmol), 4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylbenzaldehyde (0.925 g, 3.00 mmol), NaHSO3 (94%, 0.468 g, 4.50 mmol), and p-TsOH«H2O (0.171 g, 0.900 mmol) in DMA (10.0 mL) was heated at 1400C for 16 hours. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was diluted with EtOAc (50 mL), washed with water (50 mL), then brine (50 mL), dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure, to provide 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one as an off-white solid. The crude material was used directly in the next step without characterization.[0269] Following the method described for desilylation using TBAF in Example 33 below, the title compound was made from 2-(4-(2-(tert- butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one in 21% yield and was isolated as a white solid. 1H NMR (300 MHz, DMSO-Cf6): delta 12.32 (s, 1 H), 7.90 (s, 2H), 7.82-7.55 (m, 2H), 7.48 (dd, J = 7.54, 1.35 Hz, 1 H), 4.90 (t, J = 5.51 Hz, 1 H), 3.86 (t, J = 4.90 Hz, 2H), 3.77-3.68 (m, 2H), 2.32 (s, 6H). MS (APCI) m/z 345 [Ci8Hi7CIN2O3+H]+.
49%	With ethanol; ammonia; at 20℃; for 2h;	A mixture of <strong>[20829-96-3]5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione</strong> (3.50 g, 17.7 mmol) and 2 M NH3 in EtOH (11.5 mL, 23.0 mmol) and EtOH (10.0 mL) was stirred at room temperature for 2 hours. The volatiles were removed under reduced pressure, the residue was triturated with water (50 mL), and the solid was filtered, to provide 2-amino-6-chlorobenzamide (1.60 g, 49%) as a tan solid
	With ammonium carbonate; In 1,4-dioxane; at 60℃;	General procedure: Compound 13 was prepared according to the procedurepreviously reported.37 A suspension of isatoic anhydride 12 (40mmol), ammonium carbonate (160 mmol), and 1,4-dioxane(150 mL) was heated at 60 C. After being stirred for 5-8 h,the reaction mixture was cooled to room temperature andevaporated under reduced pressure, and then water (200 mL)was added to the residue, which was extracted three times withEtOAc (300 mL). The organic layer was washed with brine(100 mL), dried over anhydrous Na2SO4, filtered, andconcentrated to afford compound 13 in yields of 80-85%.

	With ammonium carbonate; In 1,4-dioxane; at 60℃; for 8h;	General procedure: A suspension of isatoic anhydride (35 mmol), ammonium carbonate (140 mmol), and 1,4-dioxane (150 mL) was heated at 60 C. After stirring for 8 h, the reaction mixture was cooled to room temperature and evaporated underreduced pressure, and then water (200 mL) was added to the residue, which was extracted with DCM (80 mL × 3). The organic layerwas dried over anhydrous Na2SO4, and concentrated to give compound 3 in yield of 84%.
	With ammonium carbonate; In 1,4-dioxane; at 60℃; for 8h;	General procedure: A suspension of substituted isatoic anhydride (35 mmol), ammonium carbonate (140 mmol), and 1,4-dioxane (150 mL) was heated at 60 C. After stirring for 8 h, the reaction mixture was cooled to room temperature and evaporated under reduced pressure, and then water (200 mL) was added to the residue, which was extracted with CH2Cl2 (380 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to give compounds 9 in yields of 63-94%.

Reference： [1]Patent: WO2010/123975,2010,A1 .Location in patent: Page/Page column 100-101
[2]Patent: US2013/281398,2013,A1 .Location in patent: Paragraph 0490
[3]Biochemistry,2017,vol. 56,p. 6491 - 6502
[4]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213
[5]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 194 - 200

32
[ 1044872-73-2 ]
[ 54166-95-9 ]
[ 1253732-65-8 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; sodium hydrogensulfite In N,N-dimethyl acetamide at 140℃; for 16h;	32 Example 32. Preparation of 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethyIphenyl)quinazolin-4(3H)-one [0266] A mixture of 2-amino-6-chlorobenzoic acid (5.00 g, 29.1 mmol) in acetonitrile (50.0 ml_) was stirred at room temperature under nitrogen. Pyridine (4.72 mL, 58.3 mmol) was added, followed by drop-wise addition of triphosgene (2.85 g, 9.60 mmol) in CH2CI2 (20.0 mL). After the addition, the mixture was heated at 55°C for 2 hours, then cooled to 25°C and stirred overnight. Water (100 mL) was added to quench, the mixture was filtered, and washed with cold CH2CI2, to provide 5-chloro-1/-/-benzo[d][1 ,3]oxazine-2,4-dione (3.54 g, 62%) as a white solid.[0267] A mixture of 5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (3.50 g, 17.7 mmol) and 2 M NH3 in EtOH (11.5 mL, 23.0 mmol) and EtOH (10.0 mL) was stirred at room temperature for 2 hours. The volatiles were removed under reduced pressure, the residue was triturated with water (50 mL), and the solid was filtered, to provide 2-amino-6-chlorobenzamide (1.60 g, 49%) as a tan solid.[0268] A mixture of 2-amino-6-chlorobenzamide (0.490 g, 3.00 mmol), 4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylbenzaldehyde (0.925 g, 3.00 mmol), NaHSO3 (94%, 0.468 g, 4.50 mmol), and p-TsOH«H2O (0.171 g, 0.900 mmol) in DMA (10.0 mL) was heated at 1400C for 16 hours. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was diluted with EtOAc (50 mL), washed with water (50 mL), then brine (50 mL), dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure, to provide 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one as an off-white solid. The crude material was used directly in the next step without characterization.[0269] Following the method described for desilylation using TBAF in Example 33 below, the title compound was made from 2-(4-(2-(tert- butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one in 21% yield and was isolated as a white solid. 1H NMR (300 MHz, DMSO-Cf6): δ 12.32 (s, 1 H), 7.90 (s, 2H), 7.82-7.55 (m, 2H), 7.48 (dd, J = 7.54, 1.35 Hz, 1 H), 4.90 (t, J = 5.51 Hz, 1 H), 3.86 (t, J = 4.90 Hz, 2H), 3.77-3.68 (m, 2H), 2.32 (s, 6H). MS (APCI) m/z 345 [Ci8Hi7CIN2O3+H]+.
	With sodium hydrogen sulfate; toluene-4-sulfonic acid In N,N-dimethyl acetamide at 140℃; for 16h;	27 Preparation of 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one A mixture of 2-amino-6-chlorobenzamide (0.490 g, 3.00 mmol), 4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylbenzaldehyde (0.925 g, 3.00 mmol), NaHSO3 (94%, 0.468 g, 4.50 mmol), and p-TsOH.H2O (0.171 g, 0.900 mmol) in DMA (10.0 mL) was heated at 140° C. for 16 hours. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was diluted with EtOAc (50 mL), washed with water (50 mL), then brine (50 mL), dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure, to provide 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one as an off-white solid

Reference： [1]Current Patent Assignee: RESVERLOGIX CORP - WO2010/123975, 2010, A1 Location in patent: Page/Page column 100-101
[2]Current Patent Assignee: ZENITH CAPITAL CORP - US2013/281398, 2013, A1 Location in patent: Paragraph 0488; 0491

33
[ 59046-72-9 ]
[ 54166-95-9 ]
[ 1364405-95-7 ]
(R)-7-chloro-4b,5-dihydro-12-phenylisoquinolino[2,1-a]quinazolin-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methyl(triphenylphosphine)gold(I); (S)-3,3'-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate In 1,2-dichloro-ethane at -5 - 20℃; for 80h; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

Reference： [1]Patil, Nitin T.; Mutyala, Anil Kumar; Konala, Ashok; Tella, Ramesh Babu [Chemical Communications, 2012, vol. 48, # 25, p. 3094 - 3096]

34
C₁₆H₁₃Cl₂NO₃S [ No CAS ]
[ 54166-95-9 ]
[ 1374021-21-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In chloroform at 10℃; for 36h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

Reference： [1]Cheng, Dao-Juan; Tian, Yu; Tian, Shi-Kai [Advanced Synthesis and Catalysis, 2012, vol. 354, # 6, p. 995 - 999]

35
[ 2148-56-3 ]
[ 54166-95-9 ]

Yield	Reaction Conditions	Operation in experiment
83%		To a solution of <strong>[2148-56-3]2-amino-6-chlorobenzoic acid</strong> (2.00 g, 11.65 mmol) in anhydrous THF (20 mL) were added 4-methylmorpholine (1.40 mL, 12.82 mmol), HOBT (1.73 g, 12.82 mmol), and EDCI (2.45 g, 12.82 mmol); the reaction mixture was stirred at room temperature for 30 minutes. 50% (v/v) Ammonium hydroxide solution (10 mL, 132.0 mmol) was added and the mixture was stirred at room temperature for 23 hours. Solvent was evaporated to about 20 mL, poured into aqueous NaHCO3 solution (200 mL) and extracted with ethyl acetate (7100 mL). The organic phase was washed with water (3100 mL), dried (Na2SO4), filtered, and evaporated, to give 2-amino-6-chlorobenzamide as a white solid. Yield: 1.65 g (83%)
83%		Example 87 Preparation of 5-Chloro-2-(3,5-dimethyl-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)quinazolin-4(3H)-one To a solution of <strong>[2148-56-3]2-amino-6-chlorobenzoic acid</strong> (2.00 g, 11.65 mmol) in anhydrous THF (20 mL) were added 4-methylmorpholine (1.40 mL, 12.82 mmol), HOBT (1.73 g, 12.82 mmol), and EDCl (2.45 g, 12.82 mmol); the reaction mixture was stirred at room temperature for 30 minutes. 50% (v/v) Ammonium hydroxide solution (10 mL, 132.0 mmol) was added and the mixture was stirred at room temperature for 23 hours. Solvent was evaporated to about 20 mL, poured into aqueous NaHCO3 solution (200 mL) and extracted with ethyl acetate (7100 mL). The organic phase was washed with water (3100 mL), dried (Na2SO4), filtered, and evaporated, to give 2-amino-6-chlorobenzamide as a white solid. Yield: 1.65 g (83%).
	With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20℃; for 15h;	General procedure: The syntheses of compounds 3a-3x were mainly referred to literature method [35]. A mixture of 1a-1q, 1w, 1x (2mmol), EDC?HCl (575mg, 3mmol), HOBt (446mg, 3.3mmol), NH4Cl (348mg, 6.5mmol) and DIPEA (2.3mL, 13mmol) in DMSO (7mL) was stirred at room temperature for 15h. The mixture was extracted with EtOAc three times, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 3a-3q, 3w, 3x. A mixture of 2r-2v (2mmol) and NH3·H2O (25-28wt%, 80mmol) in sealed tube was heated at 100C for 12h. The mixture was cooled to room temperature and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 3r-3v.

Reference： [1]Patent: US2013/281399,2013,A1 .Location in patent: Paragraph 0677
[2]Patent: US9238640,2016,B2 .Location in patent: Page/Page column 120
[3]Patent: US2013/281398,2013,A1
[4]European Journal of Medicinal Chemistry,2018,vol. 152,p. 235 - 252
[5]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213
[6]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 194 - 200

36
[ 54166-95-9 ]
[ 1246250-78-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydrogensulfite; toluene-4-sulfonic acid / N,N-dimethyl acetamide / 23 h / 120 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / N,N-dimethyl-formamide / 27 h / 20 °C
	Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; sodium hydrogensulfite / N,N-dimethyl acetamide / 23 h / 120 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / N,N-dimethyl-formamide / 27 h / 20 °C

Reference： [1]Current Patent Assignee: ZENITH CAPITAL CORP - US2013/281399, 2013, A1
[2]Current Patent Assignee: RESVERLOGIX CORP - US9238640, 2016, B2

37
[ 54166-95-9 ]
[ 1246250-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydrogensulfite; toluene-4-sulfonic acid / N,N-dimethyl acetamide / 23 h / 120 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / N,N-dimethyl-formamide / 27 h / 20 °C 3: N,N-dimethyl-formamide / 25 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid; sodium hydrogensulfite / N,N-dimethyl acetamide / 23 h / 120 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / N,N-dimethyl-formamide / 27 h / 20 °C 3: N,N-dimethyl-formamide / 25 h / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: ZENITH CAPITAL CORP - US2013/281399, 2013, A1
[2]Current Patent Assignee: RESVERLOGIX CORP - US9238640, 2016, B2

38
[ 1039948-89-4 ]
[ 54166-95-9 ]
[ 1246250-77-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 120℃; for 23.0h;Inert atmosphere;	<strong>[1039948-89-4]4-(2-hydroxyethoxy)-3,5-dimethylbenzaldehyde</strong> (0.70 g, 3.58 mmol), 2-amino-6-chlorobenzamide (0.60 g, 3.51 mmol), sodium bisulfite (0.71 g, 3.86 mmol) and p-toluenesulfonic acid monohydrate (0.133 g, 0.699 mmol) in anhydrous N,N-dimethyl acetamide (14 mL) were heated at 120 C. under nitrogen for 23 hours. The solvent was evaporated and the white solid was triturated with water (50 mL), filtered, and washed with water (20 mL). The solid was dried in vacuo and triturated with Et2O (20 mL), filtered, and dried to give 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one as a white solid. Yield: 0.77 g, (64%)
64%	With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 120℃; for 23.0h;Inert atmosphere;	4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde (0.70 g, 3.58 mmol), 2-amino-6-chlorobenzamide (0.60 g, 3.51 mmol), sodium bisulfite (0.71 g, 3.86 mmol) and p-toluenesulfonic acid monohydrate (0.133 g, 0.699 mmol) in anhydrous N,N-dimethyl acetamide (14 mL) were heated at 120 C. under nitrogen for 23 hours. The solvent was evaporated and the white solid was triturated with water (50 mL), filtered, and washed with water (20 mL). The solid was dried in vacuo and triturated with Et2O (20 mL), filtered, and dried to give 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one as a white solid. Yield: 0.77 g, (64%).

Reference： [1]Patent: US2013/281399,2013,A1 .Location in patent: Paragraph 0678
[2]Patent: US9238640,2016,B2 .Location in patent: Page/Page column 120

39
[ 54166-95-9 ]
[ 197638-78-1 ]
[ 1246249-84-2 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; sodium hydrogensulfite at 140℃; for 18h;	41 Preparation of 5-Chloro-2-(4-(4-isopropylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one A solution of 2-amino-6-chlorobenzamide (0.314 g, 1.85 mmol) and 4-(4-isopropylpiperazin-1-yl)benzaldehyde (0.430 g, 1.85 mmol) in DMA (25 mL) were treated with p-TsOH (0.035 g, 0.185 mmol) and NaHSO3 (0.212 g, 2.04 mmol), and the mixture was heated at 140° C. for 18 hours. Then, the mixture was cooled, diluted with CH2Cl2 (200 mL), and washed with saturated NaHCO3 (100 mL). The organic phase was dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography, eluting with 1:1 CH2Cl2/92:7:1 CHCl3/MeOH/concentrated NH4OH to 100% 92:7:1 CHCl3/MeOH/concentrated NH4OH to 100% 6:3:1 CHCl3/MeOH/concentrated NH4OH. The resulting solids were rechromatographed with 9:1 CH2Cl2/MeOH to afford the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 12.24 (br s, 1H), 8.11 (d, J=8.8 Hz, 2H), 7.66-7.71 (m, 1H), 7.59 (d, J=7.9 Hz, 1H), 7.42 (d, J=7.4 Hz, 1H), 7.03 (d, J=8.6 Hz, 2H), 3.28-3.34 (m, 4H), 2.64-2.73 (m, 1H), 2.55-2.59 (m, 4H), 1.01 (d, J=6.4 Hz, 6H). ESI MS m/z 383 [M+H]+
	With toluene-4-sulfonic acid; sodium hydrogensulfite In N,N-dimethyl acetamide at 140℃; for 18h;	42 Preparation of 5-Chloro-2-(4-(4-isopropylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one Example 42 Preparation of 5-Chloro-2-(4-(4-isopropylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one A solution of 2-amino-6-chlorobenzamide (0.314 g, 1.85 mmol) and 4-(4-isopropylpiperazin-1-yl)benzaldehyde (0.430 g, 1.85 mmol) in DMA (25 mL) were treated with p-TsOH (0.035 g, 0.185 mmol) and NaHSO3 (0.212 g, 2.04 mmol), and the mixture was heated at 140° C. for 18 hours. Then, the mixture was cooled, diluted with CH2Cl2 (200 mL), and washed with saturated NaHCO3 (100 mL). The organic phase was dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography, eluting with 1:1 CH2Cl2/92:7:1 CHCl3/MeOH/concentrated NH4OH to 100% 92:7:1 CHCl3/MeOH/concentrated NH4OH to 100% 6:3:1 CHCl3/MeOH/concentrated NH4OH. The resulting solids were rechromatographed with 9:1 CH2Cl2/MeOH to afford the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 12.24 (br s, 1H), 8.11 (d, J=8.8 Hz, 2H), 7.66-7.71 (m, 1H), 7.59 (d, J=7.9 Hz, 1H), 7.42 (d, J=7.4 Hz, 1H), 7.03 (d, J=8.6 Hz, 2H), 3.28-3.34 (m, 4H), 2.64-2.73 (m, 1H), 2.55-2.59 (m, 4H), 1.01 (d, J=6.4 Hz, 6H). ESI MS m/z 383 [M+H]+.

Reference： [1]Current Patent Assignee: ZENITH CAPITAL CORP - US2013/281399, 2013, A1 Location in patent: Paragraph 0526; 0527
[2]Current Patent Assignee: RESVERLOGIX CORP - US9238640, 2016, B2 Location in patent: Page/Page column 82; 83

40
[ 53293-00-8 ]
[ 54166-95-9 ]
6,7,8,9-tetrahydro-1-chloro-9-methylene-11H-pyrido[2,1-b]quinazolin-11-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C 1.2: 12 h / 20 °C 2.1: silver trifluoromethanesulfonate / toluene / 3 h / 20 - 80 °C / Inert atmosphere; Sealed tube

Reference： [1]Wang, Hengshuai; Jiao, Shengchao; Chen, Kerong; Zhang, Xu; Zhao, Linxiang; Liu, Dan; Zhou, Yu; Liu, Hong [Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 416 - 424]

41
[ 53293-00-8 ]
[ 54166-95-9 ]
2-(4-pentynyl)-5-chloro-4(3H)-quinazolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: hex-5-ynoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Stage #2: 2-amino-6-chlorobenzamide In dichloromethane at 20℃; for 12h;	General procedure for the synthesis of substrates 6A-6Land 8A-8L: General procedure: To a solution of 5-hexynoic acid (3.0 mmol) in dryCH2Cl2 (5 mL) was added EDCI (3.1 mmol) and HOBt(3.1 mmol). The resulting mixture was stirred at rt for 2 h. Then substituted or unsubstituted 2-aminobenzamide (3.0 mmol) wasadded, and the reaction mixture was stirred at rt for 12 h whilebeing monitored by TLC. After the addition of H2O (10 mL) themixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were combined and concentrated under vacuumto give the amide intermediate.

Reference： [1]Wang, Hengshuai; Jiao, Shengchao; Chen, Kerong; Zhang, Xu; Zhao, Linxiang; Liu, Dan; Zhou, Yu; Liu, Hong [Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 416 - 424]

42
[ 6089-09-4 ]
[ 54166-95-9 ]
2-(3-butynyl)-5-chloro-4(3H)-quinazolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-pentynoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Stage #2: 2-amino-6-chlorobenzamide In dichloromethane at 20℃; for 12h;	General procedure for the synthesis of substrates 6A-6Land 8A-8L: General procedure: To a solution of 5-hexynoic acid (3.0 mmol) in dryCH2Cl2 (5 mL) was added EDCI (3.1 mmol) and HOBt(3.1 mmol). The resulting mixture was stirred at rt for 2 h. Then substituted or unsubstituted 2-aminobenzamide (3.0 mmol) wasadded, and the reaction mixture was stirred at rt for 12 h whilebeing monitored by TLC. After the addition of H2O (10 mL) themixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were combined and concentrated under vacuumto give the amide intermediate.

Reference： [1]Wang, Hengshuai; Jiao, Shengchao; Chen, Kerong; Zhang, Xu; Zhao, Linxiang; Liu, Dan; Zhou, Yu; Liu, Hong [Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 416 - 424]

43
[ 6089-09-4 ]
[ 54166-95-9 ]
2,3-dihydro-1-methylene-8-chloro-pyrrolo[2,1-b]quinazolin-9(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C 1.2: 12 h / 20 °C 2.1: silver trifluoromethanesulfonate / toluene / 3 h / 20 - 80 °C / Inert atmosphere; Sealed tube

Reference： [1]Wang, Hengshuai; Jiao, Shengchao; Chen, Kerong; Zhang, Xu; Zhao, Linxiang; Liu, Dan; Zhou, Yu; Liu, Hong [Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 416 - 424]

44
[ 54166-95-9 ]
6-chloro-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

45
[ 54166-95-9 ]
(E)-6-chloro-3-((dimethylamino)methylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: trichlorophosphate / dichloromethane / 70 °C / Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

46
[ 54166-95-9 ]
(E)-6-chloro-3-((diethylamino)methylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: trichlorophosphate / dichloromethane / 48 h / Reflux; Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

47
[ 54166-95-9 ]
(E)-6-chloro-3-(pyrrolidin-1-ylmethylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: trichlorophosphate / dichloromethane / 24 h / Reflux; Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

48
[ 54166-95-9 ]
(E)-6-chloro-3-(piperidin-1-ylmethylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: trichlorophosphate / dichloromethane / 24 h / Reflux; Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

49
[ 54166-95-9 ]
(E)-6-chloro-3-(morpholinomethylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: trichlorophosphate / dichloromethane / 24 h / Reflux; Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

50
[ 54166-95-9 ]
(E)-6-chloro-3-((4-methylpiperazin-1-yl)methylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: trichlorophosphate / dichloromethane / 70 °C / Inert atmosphere 4: dmap / dichloromethane; ethanol / 70 °C / Sealed tube; Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

51
[ 54166-95-9 ]
(E)-6-chloro-3-((4-ethylpiperazin-1-yl)methylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: trichlorophosphate / dichloromethane / 70 °C / Inert atmosphere 4: dmap / dichloromethane; ethanol / 70 °C / Sealed tube; Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

52
[ 54166-95-9 ]
(E)-6-chloro-3-(2-ethylbutylidene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: potassium <i>tert</i>-butylate / dichloromethane / 1 h / Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

53
[ 54166-95-9 ]
(E)-6-chloro-3-(cyclohexylmethylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: potassium <i>tert</i>-butylate / dichloromethane / 1 h / Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

54
[ 54166-95-9 ]
(E)-6-chloro-3-((tetrahydro-2H-pyran-4-yl)methylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: potassium <i>tert</i>-butylate / dichloromethane / 1 h / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / dichloromethane / 0.08 h / Inert atmosphere 3.2: 1 h / Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]
[2]Sutherell, Charlotte L.; Ley, Steven V. [Synthesis, 2017, vol. 49, # 1, p. 135 - 144]

55
[ 54166-95-9 ]
(E)-6-chloro-3-((1-methylpiperidin-4-yl)methylene)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: potassium <i>tert</i>-butylate / dichloromethane / 1 h / Inert atmosphere

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]

56
[ 54166-95-9 ]
[ 4635-59-0 ]
2-(4-chlorobutanamido)-6-chlorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
93%	With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	Synthesisof 2-(4-chlorobutanamido)-benzamides: general procedure A General procedure: Asolutionoftheappropriatesubstituted2-aminobenzamide(1.0eq)inTHF(2.5mLpermmolsubstrate)wascooledto0°Candtriethylamine(2.0eq)thentheappropriateacidchloride(1.2eq)inTHF(2mLpermmolsubstrate)wereaddedtothestirredsolution.ThereactionwasstirredatroomtemperatureuntilcompletionasindicatedbyTLC,whenthemixturewasdilutedwithEtOAcandquenchedwithNaHSO4(20mL).TheaqueousphasewasextractedwithEtOAc(320mL),combinedorganicphasesdriedoverMgSO4,excesssolventremovedinvacuoandtheresiduepurifiedbyFCC.

Reference： [1]Sutherell, Charlotte L.; Tallant, Cynthia; Monteiro, Octovia P.; Yapp, Clarence; Fuchs, Julian E.; Fedorov, Oleg; Siejka, Paulina; Müller, Suzanne; Knapp, Stefan; Brenton, James D.; Brennan, Paul E.; Ley, Steven V. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5095 - 5101]
[2]Sutherell, Charlotte L.; Ley, Steven V. [Synthesis, 2017, vol. 49, # 1, p. 135 - 144]

57
[ 6061-04-7 ]
[ 54166-95-9 ]
5-chloro-2-(nitromethyl)quinazolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In water at 70℃; for 2h;	General Procedure for the Synthesis of 2-(nitromethyl)quinazolin-4(1H)-ones (3a-3l) General procedure: 2-Aminobenzamides (1 mmol) and 1,1-dichloro-2-nitroethene (1.2 mmol) were added to 5 mL of water in a 25 mL round-bottom flask. Then stirred at corresponding temperature and corresponding reaction time, after completion, the product precipitated from the reaction mixture and can be easily separated by filtration, then give the pure products.

Reference： [1]Zhu, Fengjuan; Song, Runjiang; Li, Shen; Shao, Xusheng [Synlett, 2016, vol. 27, # 14, p. 2167 - 2170]

58
[ 54166-95-9 ]
5-chloro-2-(5-chloropentyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere