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[ CAS No. 1591-38-4 ] {[proInfo.proName]}

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Product Citations

Selective and Cell-Active PBRM1 Bromodomain Inhibitors Discovered through NMR Fragment Screening

Shifali Shishodia ; Raymundo Nuñez ; Brayden P. Strohmier , et al. J. Med. Chem.,2022,65(20):13714-13735. DOI: 10.1021/acs.jmedchem.2c00864 PubMed ID: 36227159

More

Abstract: PBRM1 is a subunit of the PBAF chromatin remodeling complex that uniquely contains six bromodomains. PBRM1 can operate as a tumor suppressor or tumor promoter. PBRM1 is a tumor promoter in prostate cancer, contributing to migratory and immunosuppressive phenotypes. Selective chemical probes targeting PBRM1 bromodomains are desired to elucidate the association between aberrant PBRM1 chromatin binding and cancer pathogenesis and the contributions of PBRM1 to immunotherapy. Previous PBRM1 inhibitors unselectively bind SMARCA2 and SMARCA4 bromodomains with nanomolar potency. We used our protein-detected NMR screening pipeline to screen 1968 fragments against the second PBRM1 bromodomain, identifying 17 hits with Kd values from 45 μM to >2 mM. Structure–activity relationship studies on the tightest-binding hit resulted in nanomolar inhibitors with selectivity for PBRM1 over SMARCA2 and SMARCA4. These chemical probes inhibit the association of full-length PBRM1 to acetylated histone peptides and selectively inhibit growth of a PBRM1-dependent prostate cancer cell line.

Purchased from AmBeed: 77326-36-4 ; 104-87-0 ; 2148-56-3 ; 63329-53-3 ; 1591-37-3 ; 387-45-1 ; 936-08-3 ; 1123-56-4 ; 2819989-75-6 ; 703-80-0 ; 1885-29-6 ; 115643-59-9 ; 15764-16-6 ; 487-68-3 ; 145737-61-7 ; 5779-95-3 ; 88-68-6 ; 6575-11-7 ; 77326-62-6 ; 88-65-3 ; 4635-59-0 ; 5779-94-2 ; 56043-01-7 ; 5779-93-1 ; 1591-38-4 ; 446-52-6 ; 62803-47-8 ; 1885-31-0 ; 620-23-5 ; 54166-95-9 ; 22179-72-2 ; 529-20-4 ; 100-52-7 ; 123-11-5 ; 1711-06-4 ; 454-89-7 ; 170875-01-1 ; 883032-29-9 ; 2819989-61-0 ; 1915012-21-3 ; 2819989-58-5 ; 2819989-60-9 ; 2819989-57-4 ; 2819989-68-7 ; 2819989-67-6 ; 111478-13-8 ; 73096-42-1 ; 2835-78-1 ; 118-92-3 ; 22458-07-7 ; 80258-99-7 ; 24782-64-7 ; 1108790-90-4 ; 175204-03-2 ; 97-96-1 ; 780802-33-7 ; 89-98-5 ...More

Product Details of [ 1591-38-4 ]

CAS No. :	1591-38-4	MDL No. :	MFCD18389707
Formula :	C₈H₁₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AQAHTARDEJNYPN-UHFFFAOYSA-N
M.W :	166.18	Pubchem ID :	12264814
Synonyms :

Calculated chemistry of [ 1591-38-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.43
TPSA :	78.34 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.23
Log Po/w (XLOGP3) :	-0.17
Log Po/w (WLOGP) :	0.38
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	0.26
Consensus Log Po/w :	0.41

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.0
Solubility :	16.6 mg/ml ; 0.0997 mol/l
Class :	Very soluble
Log S (Ali) :	-1.02
Solubility :	15.9 mg/ml ; 0.0955 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.75
Solubility :	2.97 mg/ml ; 0.0179 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.25

Safety of [ 1591-38-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1591-38-4 ]

* 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 [ 1591-38-4 ]
Downstream synthetic route of [ 1591-38-4 ]

[ 1591-38-4 ] Synthesis Path-Upstream 1~2

1
[ 1591-38-4 ]
[ 61948-59-2 ]

Reference： [1] Journal of the Chemical Society, 1948, p. 1759,1765

2
[ 1591-38-4 ]
[ 61948-86-5 ]

Reference： [1] Journal of the Chemical Society, 1948, p. 1759,1765

[ 1591-38-4 ] Synthesis Path-Downstream 1~78

1
[ 38469-85-1 ]
[ 1591-38-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With water; hydrazine hydrate; In ethanol; at 45℃; for 4h;Reflux;	Step 2 To a suspension of 2-methoxy-6-nitrobenzonitrile (2.60 g, 14.6 mmol) in ethanol (60 mL) was added hydrazine monohydrate (1.53 g, 30.7 mmol). While heating the mixture to 45 C., Raney Ni (600 mg) was added in several portions, and the mixture was stirred at 60 C. for 2 hrs. Raney Ni (300 mg) was added again, and the mixture was heated under reflux for 2 hrs. After allowing to cool to room temperature, insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the obtained concentrated residue, and the mixture was extracted with 1N hydrochloric acid. The aqueous layer was basified with 1N aqueous sodium hydroxide solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure to give 2-amino-6-methoxybenzamide as a brown powder (980 mg, 40%).

Reference： [1]Patent: US2015/329556,2015,A1 .Location in patent: Paragraph 1549
[2]Journal of the Chemical Society,1948,p. 1759,1765
[3]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933
[4]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1955,vol. 75,p. 755
Chem.Abstr.,1955,p. 13939
[5]Justus Liebigs Annalen der Chemie,1912,vol. 388,p. 34
[6]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1191 - 1194

2
[ 1591-37-3 ]
[ 1591-38-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	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.

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 5095 - 5101
[2]Synthesis,2017,vol. 49,p. 135 - 144
[3]Justus Liebigs Annalen der Chemie,1912,vol. 388,p. 34
[4]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1955,vol. 75,p. 755
Chem.Abstr.,1955,p. 13939

3
[ 64-18-6 ]
[ 1591-38-4 ]
[ 875245-80-0 ]

Reference： [1]Journal of Organic Chemistry,1952,vol. 17,p. 149,153

4
[ 3926-62-3 ]
[ 1591-38-4 ]
<i>N</i>-(2-carbamoyl-3-methoxy-phenyl)-glycine [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1912,vol. 388,p. 34

5
[ 1591-38-4 ]
[ 857977-64-1 ]

Reference： [1]Journal of the Chemical Society,1948,p. 1759,1765

6
[ 541-41-3 ]
[ 1591-38-4 ]
[ 56934-79-3 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

7
[ 5781-53-3 ]
[ 1591-38-4 ]
[ 54166-71-1 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
		EXAMPLE 23 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
		EXAMPLE 23 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11: Found: C, 52.30; H, 4.94; H, 11.40.

		EXAMPLE 23 2'-Carbamyl-3'-methoxyoxanilic acid methyl ester. 96. 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
		EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
		EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933
[2]Patent: US4054661,1977,A
[3]Patent: US4069343,1978,A
[4]Patent: US4191840,1980,A
[5]Patent: US4154961,1979,A
[6]Patent: US4160100,1979,A
[7]Patent: US3966965,1976,A

8
[ 54166-91-5 ]
[ 1591-38-4 ]
[ 54166-72-2 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

9
[ 26404-20-6 ]
[ 1591-38-4 ]
[ 54166-73-3 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

10
[ 54166-93-7 ]
[ 1591-38-4 ]
[ 54166-86-8 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

11
[ 20963-23-9 ]
[ 1591-38-4 ]
[ 54166-85-7 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

12
[ 54166-92-6 ]
[ 1591-38-4 ]
[ 54166-84-6 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

13
[ 1591-38-4 ]
[ 4755-77-5 ]
[ 54249-44-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In tetrahydrofuran; at 35℃; for 2h;Cooling with ice;	Step 3 (1550) To a solution of <strong>[1591-38-4]2-amino-6-methoxybenzamide</strong> (960 mg, 5.78 mmol) and triethylamine (701 mg, 6.93 mol) in THF (20 mL) was added dropwise ethyl chloroglyoxylate (868 mg, 6.36 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was diluted with ethyl acetate, the mixture was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The obtained concentrated residue was washed with ethanol, ethyl ((2-(aminocarbonyl)-3-methoxyphenyl)amino)(oxo)acetate to give a yellow powder (1.56 g, 100%).
		EXAMPLE 34 2'-Carbamoyl-3'-methoxyoxanilic acid ethyl ester. 100/94 6-Amino-o-anisamide (8.75 g, 0.0527 mole) is condensed with 6.2 ml (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 8.35 g of the title compound, m.p. 170-173 C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66.
		EXAMPLE 18 2'-Carbamoyl-3'-methoxyoxanilic acid ethyl ester. 100/94. 6-Amino-o-anisamide (8.75 g., 0.0527 mole) is condensed with 6.2 ml. (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 8.35 g. of the title compound, m.p. 170-173 C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66.

		EXAMPLE 18 2'-Carbamoyl-3'-methoxyoxanilic acid ethyl ester. 100/94 6-Amino-o-anisamide (8.75 g., 0.0527 mole) is condensed with 6.2 ml. (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 8.35 g. of the title compound, m.p. 170-173 C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52: Found: C, 54.36; H, 5.20; N, 10.66.
		EXAMPLE 18 2'-Carbamyl-3'-methoxyoxanilic acid ethyl ester. 100/94. 6-Amino-o-anisamide (8.75 g., 0.0527 mole) is condensed with 6.2 ml. (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 8.35 g. of the title compound, m.p. 170-173 C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66.
		EXAMPLE 34 2'-Carbamoyl-3'-methoxyoxanilic acid ethyl ester. 100/94 6-Amino-o-anisamide (8.75 g, 0.0527 mole) is condensed with 6.2 ml (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 8.35 g of the title compound, m.p. 170-173C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66.
	In pyridine; dichloromethane;	EXAMPLE 1 [2-(aminocarbonyl)-3-methoxyphenylamino]oxoacetic acid ethyl ester 6-Amino-o-anisamide(8.75 g.) is condensed with 6.2 ml. of ethyl oxalyl chloride in 100 ml. methylene chloride in the presence of 9.6 ml. of pyridine at 10 C. Aqueous work-up and evaporation of the methylene chloride followed by recrystallization from ethanol gives the title compound, m.p. 170-173 C. Anal. Calcd. for C12 H14 N2 O5: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66. Potency: 12.5 mg/kg.

Reference： [1]Patent: US2015/329556,2015,A1 .Location in patent: Paragraph 1550
[2]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933
[3]Patent: US4160100,1979,A
[4]Patent: US4069343,1978,A
[5]Patent: US4191840,1980,A
[6]Patent: US4154961,1979,A
[7]Patent: US3966965,1976,A
[8]Patent: US4137325,1979,A

14
[ 1591-38-4 ]
[ 141-75-3 ]
[ 56934-80-6 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

15
[ 1591-38-4 ]
[ 36239-09-5 ]
[ 56934-81-7 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

16
[ 1591-38-4 ]
[ 76-02-8 ]
[ 56934-82-8 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

17
[ 75-30-9 ]
[ 1591-38-4 ]
[ 81822-54-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 568 - 576

18
[ 1591-38-4 ]
[ 64470-37-7 ]
[ 64470-38-8 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 748 - 752

19
[ 1591-38-4 ]
[ 136247-88-6 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6666 - 6671

20
[ 136247-99-9 ]
[ 1591-38-4 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6666 - 6671

21
[ 1591-38-4 ]
[ 13831-31-7 ]
2-(acetoxyacetylamino)-6-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane;	EXAMPLE 12 Preparation of 2-(acetoxyacetylamino)-6-methoxybenzamide: To a solution of <strong>[1591-38-4]2-amino-6-methoxybenzamide</strong> (1.7 g) in methylene chloride (20 ml) is added pyridine (1.6 ml), and thereto is added dropwise acetoxyacetyl chloride (1.1 ml) which is cooled in an ice bath. The mixture is stirred at room temperature for 2 hours, and thereafter, the solvent is distilled off under reduced pressure. The resulting crude crystals are washed with water and then are recrystallized from ethanol to give the title compound (2.1 g) having the following physical properties. Melting point: 163 -165 C. IR (KBr) υ: 3465, 3195, 1750, 1695, 1650, 1605, 1520, 1470, 1440, 1395, 1235, 1095, 1080, 925, 815, 785, 540 cm-1. NMR (DMSO-d6) δ: 11.45 (1 H, brs), 8.05-6.84 (3 H, m), 7.91 (2 H, brs), 4.60 (2 H, s), 3.82 (3 H, s), 2.20 (3 H, s)

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 1069 - 1076
[2]Patent: US5041462,1991,A

23
[ 7732-18-5 ]
[ 3926-62-3 ]
[ 1591-38-4 ]
<i>N</i>-(2-carbamoyl-3-methoxy-phenyl)-glycine [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1912,vol. 388,p. 34

25
[ 1591-37-3 ]
concentrated NaOH-solution [ No CAS ]
[ 1591-38-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1912,vol. 388,p. 34

26
[ 1591-38-4 ]
[ 98-88-4 ]
[ 911469-34-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6847 - 6858

27
[ 1591-38-4 ]
5-hydroxy-2-phenyl-3<i>H</i>-quinazolin-4-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6847 - 6858

28
[ 1591-38-4 ]
[ 911469-38-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6847 - 6858

29
[ 1591-38-4 ]
4-morpholin-4-yl-2-phenyl-quinazolin-5-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6847 - 6858

30
[ 1591-38-4 ]
[ 81822-40-4 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 568 - 576

31
[ 1591-38-4 ]
[ 95248-85-4 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 568 - 576

32
[ 60144-52-7 ]
[ 1591-38-4 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6666 - 6671

33
[ 1591-38-4 ]
2-Acetylamino-6-hydroxy-benzamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6666 - 6671

34
[ 1591-38-4 ]
N-acetyl-6-methoxyanthranilamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6666 - 6671

35
[ 1591-38-4 ]
[ 135106-52-4 ]

Reference： [1]Journal of Organic Chemistry,1952,vol. 17,p. 149,153

36
[ 1591-38-4 ]
[ 61948-59-2 ]

Reference： [1]Journal of the Chemical Society,1948,p. 1759,1765

37
[ 1591-38-4 ]
[ 61948-86-5 ]

Reference： [1]Journal of the Chemical Society,1948,p. 1759,1765

38
[ 1591-38-4 ]
[ 858235-35-5 ]

Reference： [1]Journal of the Chemical Society,1948,p. 1759,1765

39
[ 1591-38-4 ]
4,4'-dimethoxy-1<i>H</i>,1'<i>H</i>-[2,2']biindolylidene-3,3'-dione [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1912,vol. 388,p. 34

40
[ 1591-38-4 ]
5-methoxy-3-[3-(3-methoxy-[2]piperidyl)-2-oxo-propyl]-3<i>H</i>-quinazolin-4-one; dihydrochloride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1952,vol. 17,p. 149,153

41
[ 1591-38-4 ]
<i>N</i>²-(4-chloro-phenyl)-<i>N</i>⁴-(2-diethylamino-ethyl)-5-methoxy-quinazoline-2,4-diyldiamine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1948,p. 1759,1765

42
[ 603-12-3 ]
[ 1591-38-4 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933

43
[ 35213-00-4 ]
[ 1591-38-4 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933
[2]Patent: US2015/329556,2015,A1

44
[ 1591-38-4 ]
[ 54166-74-4 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933
[2]Patent: US3966965,1976,A

45
[ 1591-38-4 ]
[ 54166-75-5 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933
[2]Patent: US3966965,1976,A

46
[ 1591-38-4 ]
[ 74-88-4 ]
[ 56934-62-4 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In N-methyl-acetamide;	EXAMPLE 49 3'-Methoxy-2'-N-Methylcarbamyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethyl acetate-water, the mixture was basified, and the ethyl acetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) of 6-amino-N-methyl-o-anisamide m.p. 186-189 C.
	With NaH; In N-methyl-acetamide;	EXAMPLE 49 3'-Methoxy-2'-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethyl acetate-water, the mixture was basified, and the ethyl acetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) Of 6-amino-N-methyl-o-anisamide m.p. 186-189 C.
	With NaH; In N-methyl-acetamide;	EXAMPLE 67 3'-Methoxy-2'-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethylacetate-water, the mixture was basified, and the ethylacetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) of 6-amino-N-methyl-o-anisamide mp. 186-189 C.

With NaH; In N-methyl-acetamide;

EXAMPLE 67 3'-Methoxy-2'-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled at 3C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethylacetate-water, the mixture was basified, and the ethylacetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) of 6-amino-N-methyl-o-anisamide mp. 186-189C.

Reference： [1]Patent: US4154961,1979,A
[2]Patent: US4191840,1980,A
[3]Patent: US4160100,1979,A
[4]Patent: US3966965,1976,A

47
isopropyl oxalyl chloride [ No CAS ]
[ 1591-38-4 ]
[ 54166-73-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 42 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 3, giving 4.74 g of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.
		EXAMPLE 25 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 12, giving 4.74 g. of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00: Found: C, 55.66; H, 5.93; N, 10.38.
		EXAMPLE 25 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 12, giving 4.74 g. of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.

		EXAMPLE 25 2'-Carbamyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 12, giving 4.74 g. of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.
		EXAMPLE 42 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 3, giving 4.74 g of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.
		EXAMPLE 42 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 3, giving 4.74 g of the title compound, m.p. 128-132C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.

Reference： [1]Patent: US4054661,1977,A
[2]Patent: US4191840,1980,A
[3]Patent: US4069343,1978,A
[4]Patent: US4154961,1979,A
[5]Patent: US4160100,1979,A
[6]Patent: US3966965,1976,A

48
n-propyl oxalyl chloride [ No CAS ]
[ 1591-38-4 ]
[ 54166-72-2 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 41 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 3, giving 4.81 g of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.
		EXAMPLE 24 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 12, giving 4.81 g. of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00: Found: C, 55.92; H, 5.93; N, 10.34.
		EXAMPLE 24 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 12, giving 4.81 g. of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.

		EXAMPLE 24 2'-Carbamyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 12, giving 4.81 g. of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.
		EXAMPLE 41 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 3, giving 4.81 g of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.
		EXAMPLE 41 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 3, giving 4.81 g of the title compound, m.p. 158-161C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.

Reference： [1]Patent: US4054661,1977,A
[2]Patent: US4191840,1980,A
[3]Patent: US4069343,1978,A
[4]Patent: US4154961,1979,A
[5]Patent: US4160100,1979,A
[6]Patent: US3966965,1976,A

49
[ 1591-38-4 ]
[ 74-88-4 ]
[ 56934-53-3 ]
[ 56934-62-4 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In N-methyl-acetamide;	EXAMPLE 49 3'-Methoxy-2'-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethyl acetate-water, the mixture was basified, and the ethyl acetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g (8%) Of 6-amino-N-methyl-o-anisamide m.p. 186-189 C. Elemental Analysis for C9 H12 N2 O2: Calculated: C, 59.98; H, 6.71; N, 15.55. Found: C, 60.42; H, 7.04; N, 15.42.

Reference： [1]Patent: US4069343,1978,A

50
[ 79-37-8 ]
[ 1591-38-4 ]
[ 64470-37-7 ]
[ 64470-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; benzene;	The potassium salt (7.27 g., 0.03 mol.) and 1.5 ml. of pryidine are stirred at 6 C. in 125 ml. of benzene, and 25 ml. of oxalyl chloride is rapidly added. After stirring 1/2 hour at 15 C. the mixture is stripped at 15 C., and scrubbed with two portions of 130 ml. of benzene at 15 C., giving a crude mixture of 1-benzyl-1H-tetrazole-5-carbonyl chloride. This preparation of the acid chloride is kept cold and used immediately for acylation. 1-Benzyl-1H-tetrazole-5-carbonyl chloride (0.06 mol.) is dissolved in methylene chloride, and added to a 5-10 C. solution of <strong>[1591-38-4]2-amino-6-methoxybenzamide</strong> (9.97 g., 0.06 mol.) and 5 ml. of pyridine in 270 ml. of methylene chloride. The reaction solution is stirred for 2 hours at room temperature, washed twice with water, twice with brine and dried over CaCl2. Evaporation of the solvent gives 23 g. of a pink solid which crystallizes from acetonitrile giving 15.7 g. of 1 benzyl-N-[2-carbamoyl-3-methoxyphenyl]-1H-tetrazole-5-carboxamide, m.p. 190-192 C. Analysis for: C17 H16 N6 O3: Calculated: C, 57.95; H, 4.58; N, 23.85; Found: C, 58.39; H, 4.63; N, 23.86.
	With pyridine; In dichloromethane; benzene;	The potassium salt (7.27 g., 0.03 mol.) and 1.5 ml. of pyridine are stirred at 6 C. in 125 ml. of benzene, and 25 ml. of oxalyl chloride is rapidly added. After stirring 1/2 hour at 15 C. the mixture is stripped at 15 C., and scrubbed with two portions of 130 ml. of benzene at 15 C., giving a crude mixture of 1-benzyl-1H-tetrazole-5-carbonyl chloride. This preparation of the acid chloride is kept cold and used immediately for acylation. 1-Benzyl-1H-tetrazole-5-carbonyl chloride (0.06 mol.) is dissolved in methylene chloride, and added to a 5-10 C. solution of <strong>[1591-38-4]2-amino-6-methoxybenzamide</strong> (9.97 g., 0.06 mol.) and 5 ml. of pyridine in 270 ml. of methylene chloride. The reaction solution is stirred for 2 hours at room temperature, washed twice with water, twice with brine and dried over CaCl2. Evaporation of the solvent gives 23 g. of a pink solid which crystallizes from acetonitrile giving 15.7 g. of 1 benzyl-N-[2-carbamoyl-3-methoxyphenyl]-1H-tetrazole-5-carboxamide, m.p. 190-192 C. Analysis for C17 H16 N6 O3: Calculated: C, 57.95; H, 4.58; N, 23.85. Found: C, 58.39; H, 4.63; N, 23.86.

Reference： [1]Patent: US4044144,1977,A
[2]Patent: US4112106,1978,A

51
[ 5271-67-0 ]
[ 1591-38-4 ]
[ 1132696-83-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1191 - 1194

52
[ 53600-33-2 ]
[ 1591-38-4 ]

Yield	Reaction Conditions	Operation in experiment
98%		To a solution of 2-amino-6-methoxybenzoic acid (9.0 g, 53.8 mmol) in THF (270 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (23.7 g, 123.7 mmol) and hydroxybenzotriazole (23.9 g, 156.0 mmol). The mixture was stirred at rt for 30 min, then N-methylmorpholine (18.2 g, 180.3 mmol) and NH4OH ( 50 vol % in H2O, 36 mL) were added. The reaction mixture was then stirred for 18 h at rt. After that time the reaction was concentrated under reduced pressure and diluted with ethyl acetate (600 mL). The organic phase was washed with brine (2×100 mL), dried over Na2SO4 and concentrated under reduced pressure to give 2-amino-6-methoxybenzamide (8.80 g, 98%) as a light yellow solid: 1H NMR (400 MHz, DMSO-d6): δ 7.55 (br s, 1H), 7.29 (br s, 1H), 7.01 (t, J=8.4 Hz, 1H), 6.36 (br s, 2H), 6.30 (dd, J=8.4, 0.8 Hz, 1H), 6.17 (dd, J=8.0, 1.2 Hz, 1H), 3.76 (s, 3H)
65%		To a stirred solution of 2-amino-6-methoxy-benzoicacid (3.00 g, 17.9 mmol) in THF (90 mL), EDCI (7.89 g, 41.1 mmol) and HOBt (7.95 g, 51.9 mmol) were added and stirred at room temperature for 30 minutes then N-methylmorpholine (6.15 g, 60.0 mmol) and aqueous 50% v/v NH4OH (12 mL, 171.4 mmol) was added. The mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure and the residue was extracted with ethylacetate (4*100 mL), the combined organic phase was washed with water and brine, and dried over anhydrous sodium sulfate; the solvent was evaporated to give 2-amino-6-methoxy-benzamide as an off-white solid. Yield: 1.90 g, (65%)
65%		Example 67 Preparation of 2-(3,5-Dimethyl-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-5-methoxyquinazolin-4(3H)-one To a stirred solution of 2-amino-6-methoxy-benzoic acid (3.00 g, 17.9 mmol) in THF (90 mL), EDCl (7.89 g, 41.1 mmol) and HOBt (7.95 g, 51.9 mmol) were added and stirred at room temperature for 30 minutes then N-methylmorpholine (6.15 g, 60.0 mmol) and aqueous 50% v/v NH4OH (12 mL, 171.4 mmol) was added. The mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure and the residue was extracted with ethylacetate (4*100 mL), the combined organic phase was washed with water and brine, and dried over anhydrous sodium sulfate; the solvent was evaporated to give 2-amino-6-methoxy-benzamide as an off-white solid. Yield: 1.90 g, (65%).

Reference： [1]Patent: US2014/140956,2014,A1 .Location in patent: Paragraph 0860
[2]Patent: US2013/281399,2013,A1 .Location in patent: Paragraph 0615
[3]Patent: US9238640,2016,B2 .Location in patent: Page/Page column 103
[4]ChemMedChem,2021,vol. 16,p. 891 - 897
[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

53
[ 1591-38-4 ]
[ 1246250-34-9 ]

Reference： [1]Patent: US2013/281399,2013,A1
[2]Patent: US9238640,2016,B2

54
[ 1591-38-4 ]
[ 1246250-33-8 ]

Reference： [1]Patent: US2013/281399,2013,A1
[2]Patent: US9238640,2016,B2

55
[ 1039948-89-4 ]
[ 1591-38-4 ]
[ 1044871-20-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 115℃; for 20.0h;	To a solution of 2-amino-6-methoxy-benzamide (1.00 g, 6.01 mmol) and <strong>[1039948-89-4]4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde</strong> (1.28 g, 6.59 mmol) in N,N-dimethylacetamide (15 mL) were added NaHSO3 (58.5 wt %, 0.68 g, 6.50 mmol) and p-TSA (0.23 g, 1.20 mmol) and the reaction mixture was heated at 115 C. for 20 hours, and cooled to room temperature. N,N-dimethylacetamide was removed under reduced pressure. The residue was diluted with water (50 mL), stirred for 30 minutes, and then filtered. The solid was suspended in dichloromethane (30 mL), stirred for 1 h, filtered, and dried under vacuum to give 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-5-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.1 g (55%)
55%	With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 115℃; for 20.0h;	To a solution of 2-amino-6-methoxy-benzamide (1.00 g, 6.01 mmol) and <strong>[1039948-89-4]4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde</strong> (1.28 g, 6.59 mmol) in N,N-dimethylacetamide (15 mL) were added NaHSO3 (58.5 wt %, 0.68 g, 6.50 mmol) and p-TSA (0.23 g, 1.20 mmol) and the reaction mixture was heated at 115 C. for 20 hours, and cooled to room temperature. N,N-dimethylacetamide was removed under reduced pressure. The residue was diluted with water (50 mL), stirred for 30 minutes, and then filtered. The solid was suspended in dichloromethane (30 mL), stirred for 1 h, filtered, and dried under vacuum to give 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-5-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.1 g (55%).

Reference： [1]Patent: US2013/281399,2013,A1 .Location in patent: Paragraph 0616
[2]Patent: US9238640,2016,B2 .Location in patent: Page/Page column 103; 104

56
[ 1610373-19-7 ]
[ 1591-38-4 ]
[ 1610373-96-0 ]

Yield	Reaction Conditions	Operation in experiment
0.41 g	With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 120℃; for 14h;	To a solution of 5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylsulfonyl)phenyl)-picolinaldehyde (0.54 g, 1.50 mmol) and <strong>[1591-38-4]2-amino-6-methoxybenzamide</strong> (0.274 g, 1.65 mmol) in N,N-dimethylacetamide (15 ml) was added NaHSO3 (58.5 wt %, 0.41 g, 2.25 mmol) and p-toluenesulfonic acid monohydrate (0.057 g, 0.30 mmol). The reaction mixture was stirred at 120 C. for 14 h. After that time the reaction was cooled to rt, concentrated under reduced pressure, diluted with water (100 mL) and the precipitated solids were collected by filtration, washed with water and dried under vacuum. The product was washed with diethyl ether and dried to give 2-(5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylsulfonyl)-phenyl)pyridin-2-yl)-5-methoxyquinazolin-4(3H)-one (0.41 g) as a brown solid: ESI MS m/z 582 [M+H]+.

Reference： [1]Patent: US2014/140956,2014,A1 .Location in patent: Paragraph 0877

57
[ 1610373-70-0 ]
[ 1591-38-4 ]
[ 1610372-83-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 120℃; for 20h;	To a solution of 5-methoxy-6-(4-(methylsulfinyl)phenyl)picolinaldehyde (0.83 g, 3.0 mmol) in N,N-dimethylacetamide (30 mL) was added <strong>[1591-38-4]2-amino-6-methoxybenzamide</strong> (0.50 g, 3.0 mmol) followed by NaHSO3 (0.47 g, 4.5 mmol) and p-toluenesulfonic acid monohydrate (0.57 g, 3.0 mmol). The reaction was heated at 120 C. for 20 h. After that time the reaction was cooled to rt, concentrated under reduced pressure and diluted with water (10 mL) and saturated Na2CO3 (2 mL). The precipitated solids were collected by filtration, washed with water and dried under vacuum. The product was purified by flash column chromatography (silica gel, 98:2 dichloromethane/methanol) followed by trituration with methanol to give 5-methoxy-2-(5-methoxy-6-(4-(methylsulfinyl)phenyl)pyridin-2-yl)quinazolin-4(3H)-one (0.758 g, 60%) as a white solid: mp 308-310 C.; 1H NMR (400 MHz, DMSO-d6): δ 11.36 (br s, 1H), 8.40 (d, J=8.4 Hz, 1H), 8.30 (d, J=8.8 Hz, 2H), 7.84-7.76 (m, 3H), 7.72 (t, J=8.4 Hz, 1H), 7.29 (d, J=7.6 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H), 3.97 (s, 3H), 3.88 (s, 3H), 2.80 (s, 3H); ESI MS m/z 422 [M+H]+.

Reference： [1]Patent: US2014/140956,2014,A1 .Location in patent: Paragraph 0858; 0861

58
[ 1591-38-4 ]
[ 1610372-88-7 ]

Reference： [1]Patent: US2014/140956,2014,A1

59
[ 1591-38-4 ]
[ 1610373-97-1 ]

Reference： [1]Patent: US2014/140956,2014,A1

60
[ 1591-38-4 ]
[ 1610372-90-1 ]

Reference： [1]Patent: US2014/140956,2014,A1

61
[ 1591-38-4 ]
[ 57101-43-6 ]

Reference： [1]Patent: US2015/329556,2015,A1

62
[ 1591-38-4 ]
6-methoxy-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 5095 - 5101
[2]Synthesis,2017,vol. 49,p. 135 - 144

63
[ 1591-38-4 ]
(E)-3-((dimethylamino)methylene)-6-methoxy-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 5095 - 5101

64
[ 1591-38-4 ]
6-hydroxy-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 5095 - 5101

65
[ 1591-38-4 ]
(E)-3-((dimethylamino)methylene)-6-hydroxy-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 5095 - 5101

66
[ 1591-38-4 ]
[ 4635-59-0 ]
2-(4-chlorobutanamido)-6-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	General procedure: Asolutionoftheappropriatesubstituted2-aminobenzamide(1.0eq)inTHF(2.5mLpermmolsubstrate)wascooledto0Candtriethylamine(2.0eq)thentheappropriateacidchloride(1.2eq)inTHF(2mLpermmolsubstrate)wereaddedtothestirredsolution.ThereactionwasstirredatroomtemperatureuntilcompletionasindicatedbyTLC,whenthemixturewasdilutedwithEtOAcandquenchedwithNaHSO4(20mL).TheaqueousphasewasextractedwithEtOAc(320mL),combinedorganicphasesdriedoverMgSO4,excesssolventremovedinvacuoandtheresiduepurifiedbyFCC.

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 5095 - 5101
[2]Synthesis,2017,vol. 49,p. 135 - 144

67
[ 77326-36-4 ]
[ 1591-38-4 ]

Reference： [1]Synthesis,2017,vol. 49,p. 135 - 144

68
[ 1591-38-4 ]
C₁₀H₁₀BrN₃O₂ [ No CAS ]

Reference： [1]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213

69
[ 1591-38-4 ]
[ 1369962-90-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of anthranilamide (30 mmol) in 1 N HCl (120 mL) was stirred at 0 C for 20 min. Then, sodium nitrite (60 mmol) dissolved in deionized water (100 mL) was added dropwise to the above solution for 40 min. After another 2 h of stirring at 0 C, 30% NaOH solution was added slowly to adjust the pH to 8.0. The reaction mixture was allowed to stir vigorously for 15 min. The precipitated product was filtered off with suction, washed with deionized water (200 mL), and dried to afford compound 4 in yield of 82%.
		General procedure: A solution of anthranilamide (30 mmol) in 1N HCl (120 mL) was stirred at 0 C for 20 min. Then, sodium nitrite (60 mmol) dissolved in deionized water (100 mL) was added dropwise to the above solution for 40 min. After another 2 h of stirringat 0 C, 30% NaOH solution was added slowly to adjustp H value to 8.0. The reaction mixture was allowed to stir vigorously for 15 min. The precipitated product was filtered, washed with deionized water (200 mL), and dried to afford compounds 10 in yields of 40-92%.
	With hydrogenchloride; sodium nitrite; In N,N-dimethyl-formamide; at 0℃; for 0.666667h;	General procedure: A solution of sodium nitrite (4.14 g, 60 mmol) in 0.5 N HCl (240 mL) was stirred at 0 C for 20 min. Then anthranilamide (3.96 g, 30 mmol) dissolved in N, N-dimethylformamide (DMF, 15 mL) was added dropwise to the above solution for 40 min. After another 1 h of stirring at 0 C, 30% aqueous ammonia was added slowly to adjust the pH to 10.0. The reaction mixture was allowed to stir vigorously for 15 min and then add acid to adjust pH 2.0. After stirring for 30 min, the precipitated product was filtered off with suction, washed with water (200 mL) and dried to afford afford the product. The yields of substituted 1,2,3-benzotriazin-4-ones in yields of 84-92%.

Reference： [1]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 194 - 200
[3]Bioorganic and medicinal chemistry letters,2020,vol. 30

70
[ 1591-38-4 ]
5-methoxy-3-(2-(4-(2-nitrobenzoyl)piperazin-1-yl)ethyl)benzo[d][1,2,3]triazin-4(3H)-one [ No CAS ]

Reference： [1]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213

71
[ 1591-38-4 ]
C₁₄H₁₉N₅O₂ [ No CAS ]

Reference： [1]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213

72
[ 67765-42-8 ]
[ 1591-38-4 ]

Yield	Reaction Conditions	Operation in experiment
	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]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 194 - 200

73
[ 1591-38-4 ]
C₁₁H₁₂BrN₃O₂ [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 194 - 200

74
[ 1591-38-4 ]
3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-5-methoxybenzo[d][1,2,3]triazin-4(3H)-one [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 194 - 200

75
[ 1591-38-4 ]
C₁₈H₁₅N₅O₄S [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,2020,vol. 30

76
[ 1591-38-4 ]
C₁₁H₁₃N₃O₃ [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,2020,vol. 30

77
[ 13139-15-6 ]
[ 1591-38-4 ]
tert-butyl (S)-(1-(5-methoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-3-methylbutyl)carbamate [ No CAS ]

Reference： [1]ChemMedChem,2021,vol. 16,p. 891 - 897

78
[ 1136-86-3 ]
[ 1591-38-4 ]
5-methoxy-2-(3,4,5-trimethoxybenzoyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With iodine; In dimethyl sulfoxide; at 110℃;	General procedure: I2 (362.25 mg, 1.43 mmol, 1.1 eq) was added to a mixture of 2j(272.77 mg, 1.3 mmol, 1 eq) and DMSO (3 mL). The solution wasstirred at 110C, then 1a1u (1 eq) in 3 mL DMSO was addeddropwise to the mixture during 1 h. After the complete disappearanceof the starting material, a sodium thiosulfate solution(0.2 g Na2S2O3 in 12 mL water) was added dropwise to the reactionsystem. Filtration and drying, the residue was purified by silica gelchromatography to yield the desired products 4a-4u.

Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 224

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Isomers

Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Acetal Formation • Acyl Group Substitution • Amide Hydrolysis • Amide Hydrolysis • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conversion of Amino with Nitro • Deprotonation of Methylbenzene • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nitrosation of Amines • Nomenclature of Ethers • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Preparation of LDA • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Ring Opening of Oxacyclopropane • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • Synthesis of Alcohols from Tertiary Ethers • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • The Nucleophilic Opening of Oxacyclopropanes • Ugi Reaction • Vilsmeier-Haack Reaction

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P378
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P401
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Ghs Hazard Statements

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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H316	Causes mild skin irritation
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H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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