[ CAS No. 953039-10-6 ] {[proInfo.proName]}

Name: 953039-10-6|2-Chloro-quinazolin-8-ol|98%
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SKU: A422904
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Product Details of [ 953039-10-6 ]

CAS No. :	953039-10-6	MDL No. :	MFCD24728919
Formula :	C₈H₅ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NFLGXMBUPVURGA-UHFFFAOYSA-N
M.W :	180.59	Pubchem ID :	59199230
Synonyms :

Safety of [ 953039-10-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H301-H311-H331	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 953039-10-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 953039-10-6 ]

[ 953039-10-6 ] Synthesis Path-Downstream 1~50

1
[ 944060-66-6 ]
[ 953039-10-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 2-chloro-8-methoxyquinazoline With boron tribromide In dichloromethane at -5 - 20℃; for 22.5833h; Stage #2: With water at 0℃; for 0.5h;	1.1 Example 1Preparation of 3-(8-( 1 -Methylpiperidin-4-yloxy)quinazolin-2-ylarnino)benzenesulfonamideStep 1. Preparation of 2-Chloroquinazolin-8-ol To a 0.55M solution of 2-chloro-8-methoxyquinazoline in DCM was added boron tribromide(2.2 eq. of a 1.0 M solution in DCM) over 5 minutes at 0 0C. The reaction mixture was stirred at ambient temperature for 22 hours, and then cooled to -5 0C for 30 minutes. The precipitate was collected by vacuum filtration and then stirred in ice water for 30 minutes. The solid was collected by vacuum filtration and rinsed with 2-propanol. The off-white solid was dried in a desiccator to give the desired product in 79% yield. ES/MS m/z 181 (MH+).
5.84 g	With boron tribromide In dichloromethane at 20℃; for 16h; Cooling with ice;	1 Reference Example 1; Manufacture of 2-chloro-quinazolin-8-ol To 2-chloro-8-methoxy-quinazoline (8.85 g, 45.0 mmol) in DCM (91 ml), was added dropwise under ice-cooling boron tribromide (1M / DCM, 100 ml), and the mixture It was stirred at room temperature for 16 hours. The reaction mixture was cooled to -5 , and precipitated solid was filtered. The precipitated solid was washed with saturated sodium bicarbonate, to give 5.84 g 2-chloro-quinazolin-8-ol as a crude product.

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 305
[2]Current Patent Assignee: MYCHUNTER THERAPEUTICS - CN105358549, 2016, A Location in patent: Paragraph 0116; 0117; 0119; 0120; 0121

2
[ 953039-10-6 ]
[ 98-18-0 ]
3-(8-hydroxy-quinazolin-2-ylamino)-benzenesulfonamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol at 90℃; for 14h;	1.2 Step 2. Preparation of 3-(8-Hydroxyquinazolin-2-ylamino)benzenesulfonamide To a 0.3 M solution of 2-chloroquinazolin-8-ol in 2-propanol was added sulfanilamide (1.0 eq). The reaction was stirred at 90 0C for 14 hours. The hydrochloride was collected by vacuum filtration and then stirred in aqueous sodium bicarbonate. The solid was collected by vacuum filtration and rinsed with water. The off-white solid was dried in a desiccator to give the desired product in 93% yield. ESZMS wZz Sn (MH+).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 305

3
[ 953039-10-6 ]
[ 953039-17-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	With N-Bromosuccinimide; diisopropylamine In chloroform at -5 - 0℃; for 1h;	5 Example 5Preparation of 7-bromo-2-chloroquinazolin-8-olSolid NBS (1.09 g, 6.11 mmole) was added to a stirred solution of 2-chloroquinazolin-8-ol (1.10 g, 6.11 mmole) and diisopropyl amine (2.2 mL, 15.30 mmole) in CHCI3 (60 inL) at -5 0C under argon. After stirring at -5 to 0 0C for 1 hour, LCMS showed that the reaction was complete. The reaction was evaporated to a residue which was dissolved in DMSO (5 mL) and purified by prep. HPLC. The pure product was obtained as a white solid in 51% yield (800 mg, 3.08 mmole).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 312

4
[ 953039-10-6 ]
[ 953039-39-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: isopropyl alcohol With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 2-chloro-8-hydroxyquinazoline In tetrahydrofuran at 20℃; for 4h;	16.1 Example 16 -Preparation of 4-(8-isopropoxyquinazolm-2-ylamino)-N-methylbenzamide (Compound 515) PP028218.0002Step 1. Preparation of 8-O-alkylated intermediateTo a 0.30 M solution of triphenylphosphine (1.5 eq) in THF was added diethylazodicarboxyate (1.5 eq). The mixture was stirred 15 min at ambient temperature. 2-Propanol (4.0 eq) was added. The mixture was stirred 15 min at ambient temperature. 2-Chloroquinazolin-8-ol (1.0 eq) was added. The mixture was stirred an additional 4 h. The crude mixture was concentrated, purified by flash chromatography (3:1 hexanes : ethyl acetate) to give the desired product. ES/MS m/z 223 (MH+).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 321-322

5
[ 953039-10-6 ]
[ 953039-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: t-butyl 4-hydroxy piperidine-1-carboxylate With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 2-chloro-8-hydroxyquinazoline In tetrahydrofuran at 20℃; for 4h;	20.1 Example 20Synthesis of morpholino(4-(8-(ρiperidin-4-yloxy)quinazolin- PP028218.00022-ylamino)phenyl)rnethanone (Compound 538)Step 1. Preparation of 2-Chloro-8-(N-Boc-piperidin-4-yloxy)quinazolineTo a 0.30 M solution of triphenylphosphine (1.5 eq) in THF was added diethylazodicarboxylate(1.5 eq). The mixture was stirred 15 min at ambient temperature. N-Tert-butyl-4-Hydroxy-l- piperidine carboxylate (4.0 eq) was added. The mixture was stirred 15 min at ambient temperature. 2-Chloroquinazolin-8-ol (1.0 eq) was added. The mixture was stirred an additional4 h. The crude mixture was concentrated, purified by flash chromatography (3:2 hexanes: EtOAc), and concentrated to give the desired product. ES/MS m/z 364 (MH+).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 326-327

6
[ 953039-10-6 ]
2,7-dichloro-quinazolin-8-ol [ No CAS ]
2,5,8-trichloro-quinazoline [ No CAS ]
[ 953039-82-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 65% 2: 25% 3: 15%	With N-chloro-succinimide In chloroform at 40℃; for 2h;	32.1 Example 32Preparation of 5-chloro-N-(4-morpholinophenyl)-8-(piperidin-4-yloxy)quinazolin-2-amine (Compound 605) The subject compound was prepared according to the general Scheme below:Step 1. Preparation of 2,5-dichloroquinazolin-8-olTo a solution of 2-chloroquinazlin-8-ol (leq) in chloroform was added N-chlosuccinimide (leq) and the resulting mixture was heated to 400C for 2h. The chlorination goes to completion giving 2,5-dichloroquinazalin-8-ol in 65 % yield. 25% of the reaction was 2,7dichloroquinazolin-8-ol and 15% of the reaction mixture was 2,5,8-trichloro quinazolin-8-ol. The reaction mixture was concentrated and the crude was purified by silica gel. The structures of the isomers were confirmed by 1HNMR and by LC/MS. ES/MS m/z 215(MH+).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 343

7
[ 953039-10-6 ]
[ 953040-03-4 ]
[ 953039-17-3 ]
5,7-dibromo-2-chloroquinazolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide at 0℃; for 0.5h;	45.1 Example 45 Synthesis 5-bromo-N- (3- chloro-4-morpholinophenyl)-8-(piperidine-4-yloxy) quinazolin-2- amine (Compound 338)Step 1. Preparation of 5-brorno-2-chloroquinazolin-8-ol Solid NBS (leq) was added to a stirred solution of 2-chloroquinazolin-8-ol (leq) (See example 1 for synthesis) in NMP at 00C under argon. After stirring at 00C for 30min, LCMS showed that the reaction was complete. The formation of both 5-bromo (Major) and 7-bromo (Minor) isomers PP028218.0002along with 5,7 dibromo product was observed. The reaction mixture was diluted with ethyl acetate and washed with satd. sodium bicarbonate, water and brine. Dried, filtered and concentrated. The crude was purified by flash chromatography (3-5% EtOAc / Hexane) to provide 5-bromo-2-chloroquinazolin-8-ol as a white solid in 60% yield. ES/MS m/z 259.2 (MH+).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 357-358

8
[ 944060-66-6 ]
[ 953040-40-9 ]
[ 953039-10-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-chloro-8-methoxyquinazoline With boron tribromide In dichloromethane at -10 - 20℃; for 22h; Stage #2: With water at 0℃; for 1h;	57.1 Example 57Synthesis of 4-(8-(6-fluoropyridin-3-yloxy)quinazolin-2-ylamino)benzenesulfonamide (Compound 413) PP028218.0002Step 1. To a 0.13 M solution of Ia in DCM was added boron tribromide (2.0 eq. of a 1.0 M solution in DCM) dropwise at -10 0C under a nitrogen atmosphere. The reaction was allowed to warm to room temperature (dark orange color) and stirred for 22 hours. The reaction was then cooled to 0 0C (red solution and precipitate formed) and the precipitate was collected by vacuum filtration and rinsed with cold DCM. The solid was stirred in ice water for one hour then filtered off, washed with water, cold 2-propanol and hexanes. The light tan solid was dried under vacuum to give the desired product in 82 % yield as a mixture of the 2-chloro and 2- bromoquinazolin-8-ol. ES/MS m/z 181.1 and 225.0/227.0 (MH+).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 374

9
[ 953040-40-9 ]
[ 953039-10-6 ]
[ 351019-18-6 ]
[ 953040-42-1 ]
[ 953040-44-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃; for 24.0833h; Molecular sieves 4Å;	57.2 Step 2. To a 0.1 M solution of the 2-chloro and 2-bromoquinazolin-8-ol in DCM was added 4A MS followed by Cu(OACh1H2O (1.0 eq.). The solution was stirred at room temperature for 5 min. (brown color), then 2-fluorpyridine5-boronic acid was added (2.0 eq.), followed by Et3N (5 eq.). The solution turned dark green and it was allowed to stir for 24 hr. The reaction was then filtered, the filtrate was evaporated and passed through a plug of silica gel eluting with EtOAc. Upon concentration of the fractions, the desired product was obtained in 33% yield. ES/MS m/z 276.0 and 321.9/320.0 (MH+).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2 Location in patent: Page/Page column 374

10
[ 953039-10-6 ]
[ 934-22-5 ]
2-[(1H-benzo[d]imidazol-6-yl)amino]quinazolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.07 g	In isopropyl alcohol at 100 - 110℃; for 6h;	1.1 (first step) The compound of Reference Example 1 (0.97 g, 5.26 mmol) in 2-propanol solution (15 ml) and 1H- benzimidazole-6-amine (0.70 g, 5.26 mmol) was stirred at 100-110 16 hour. After the solution was cooled to room temperature, the precipitated solid was filtered. After washing with 2-propanol, and the precipitated solid was dried to give 2 - [(1H- benzo [d] imidazol-6-yl) amino] quinazolin-8-ol (1.07 g).

Reference： [1]Current Patent Assignee: MYCHUNTER THERAPEUTICS - CN105358549, 2016, A Location in patent: Paragraph 0131; 0134; 0135; 0136; 0137

11
[ 953039-10-6 ]
N-(1H-benzo[d]imidazole-6-yl)-8-{cis-4-[(tert-butyldimethylsilyl)oxy]cyclohexyl}oxyquinazolin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: isopropyl alcohol / 6 h / 100 - 110 °C 2: caesium carbonate / dimethyl sulfoxide / 1 h / 130 °C

Reference： [1]Current Patent Assignee: MYCHUNTER THERAPEUTICS - CN105358549, 2016, A

12
[ 953039-10-6 ]
4-({2-[(1H-benzo[d]imidazol-6-yl)amino]quinazolin-8-yl}oxy)cyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: isopropyl alcohol / 6 h / 100 - 110 °C 2: caesium carbonate / dimethyl sulfoxide / 1 h / 130 °C 3: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

Reference： [1]Current Patent Assignee: MYCHUNTER THERAPEUTICS - CN105358549, 2016, A

13
[ 953039-10-6 ]
4-({2-[(1H-benzo[d]imidazol-6-yl)amino]quinazolin-8-yl}oxy)cyclohexanol hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: isopropyl alcohol / 6 h / 100 - 110 °C 2: caesium carbonate / dimethyl sulfoxide / 1 h / 130 °C 3: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 4: hydrogenchloride / ethanol / 24 h / 35 - 50 °C

Reference： [1]Current Patent Assignee: MYCHUNTER THERAPEUTICS - CN105358549, 2016, A

14
[ 953039-10-6 ]
3-(8-hydroxy-quinazolin-2-ylamino)-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: isopropyl alcohol / 14 h / 90 °C 2: water; sodium hydrogencarbonate

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

15
[ 953039-10-6 ]
5-chloro-2-(4-morpholin-4-yl-phenylamino)quinazolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: isopropyl alcohol / 1 h / 90 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

16
[ 953039-10-6 ]
N-(3-chloro-8-methoxy-quinazolin-2-ylamino)-5-(dimethylaminomethyl-phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: hydrogenchloride / water; isopropyl alcohol / 120 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

17
[ 953039-10-6 ]
3-(8-(1-methyl-piperidin-4-yloxy)quinazolin-2-ylamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: isopropyl alcohol / 14 h / 90 °C 2.1: water; sodium hydrogencarbonate 3.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 3.2: 1 h / 20 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

18
[ 953039-10-6 ]
(4-(7-bromo-5-chloro-8-methoxy-quinazolin-2-ylamino)phenyl)(morpholin-4-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: N-Bromosuccinimide / chloroform 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 4: isopropyl alcohol / 16 h / 90 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

19
[ 953039-10-6 ]
5-chloro-N-(4-morpholin-4-yl-phenyl)-8-piperidin-4-yloxy-quinazolin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: isopropyl alcohol / 1 h / 90 °C 3: potassium carbonate; lithium hexamethyldisilazane / N,N-dimethyl-formamide / 0.17 h / 170 °C / Microwave irradiation 4: trifluoroacetic acid / dichloromethane / 0.5 h

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

20
[ 953039-10-6 ]
(4-(5-chloro-8-methoxy-7-(1-methyl-1H-pyrazol-4-yl)-quinazolin-2-ylamino)phenyl)morpholin-4-yl-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: N-Bromosuccinimide / chloroform 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 4: isopropyl alcohol / 16 h / 90 °C 5: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane / 0.17 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

21
[ 953039-10-6 ]
4-(7-(1-methyl-1H-pyrrol-3-yl)-8-(piperidin-4-yloxy)quinazolin-2-ylamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 3.1: potassium <i>tert</i>-butylate / isopropyl alcohol / 2.5 h / 105 °C 3.2: pH 4 4.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane / 1.5 h / 90 - 95 °C 5.1: hydrogenchloride / 1,4-dioxane; 1,2-dimethoxyethane / 2 h
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; diisopropylamine / chloroform / 1 h / -5 - 0 °C 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 3.1: potassium <i>tert</i>-butylate / isopropyl alcohol / 2.5 h / 105 °C 3.2: pH 4 4.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane / 1.5 h / 90 - 95 °C 5.1: hydrogenchloride / 1,4-dioxane; 1,2-dimethoxyethane / 2 h

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

22
[ 953039-10-6 ]
5-bromo-N-(3-chloro-4-morpholinophenyl)-8-(piperidin-4-yloxy)quinazolin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: isopropyl alcohol / 110 °C 4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

23
[ 953039-10-6 ]
N-(3-chloro-4-morpholin-4-yl-phenyl)-5-methyl-8-piperidin-4-yloxy-quinazolin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: isopropyl alcohol / 110 °C 4.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 0.17 h / 120 °C / Microwave irradiation 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

24
[ 953039-10-6 ]
tert-butyl 4-(7-bromo-2-(4-sulfamoyl-phenylamino)quinazolin-8-yloxy)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 3.1: potassium <i>tert</i>-butylate / isopropyl alcohol / 2.5 h / 105 °C 3.2: pH 4
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; diisopropylamine / chloroform / 1 h / -5 - 0 °C 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 3.1: potassium <i>tert</i>-butylate / isopropyl alcohol / 2.5 h / 105 °C 3.2: pH 4

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

25
[ 953039-10-6 ]
tert-butyl 4-(5-chloro-2-(4-morpholin-4-yl-phenylamino)-quinazolin-8-yloxy)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: isopropyl alcohol / 1 h / 90 °C 3: potassium carbonate; lithium hexamethyldisilazane / N,N-dimethyl-formamide / 0.17 h / 170 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

26
[ 953039-10-6 ]
C₂₉H₃₅N₅O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.25 h / 20 °C 1.2: 4 h / 20 °C 2.1: isopropyl alcohol / 14 h / 130 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

27
[ 953039-10-6 ]
C₂₉H₃₄N₆O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 3.1: potassium <i>tert</i>-butylate / isopropyl alcohol / 2.5 h / 105 °C 3.2: pH 4 4.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane / 1.5 h / 90 - 95 °C
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; diisopropylamine / chloroform / 1 h / -5 - 0 °C 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 3.1: potassium <i>tert</i>-butylate / isopropyl alcohol / 2.5 h / 105 °C 3.2: pH 4 4.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane / 1.5 h / 90 - 95 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

28
[ 953039-10-6 ]
tert-butyl 4-(2-(2-chloro-4-morpholin-4-yl-phenylamino)-5-methyl-quinazolin-8-yloxy)-piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: isopropyl alcohol / 110 °C 4.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 0.17 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

29
[ 953039-10-6 ]
[ 953040-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: isopropyl alcohol / 110 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

30
[ 953039-10-6 ]
4-(8-isopropoxy-quinazolin-2-ylamino)-N-methyl-benzamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.25 h / 20 °C 1.2: 4 h / 20 °C 2.1: isopropyl alcohol / 14 h / 100 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

31
[ 953039-10-6 ]
(morpholin-4-yl)(4-(8-piperidin-4-yloxy-quinazolin-2-ylamino)phenyl)methanone trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.25 h / 20 °C 1.2: 4 h / 20 °C 2.1: isopropyl alcohol / 14 h / 130 °C 3.1: dichloromethane / 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

32
[ 953039-10-6 ]
4-(7-(1-methyl-1H-pyrrol-3-yl)-8-(piperidin-4-yloxy)quinazolin-2-ylamino)benzenesulfonamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 3.1: potassium <i>tert</i>-butylate / isopropyl alcohol / 2.5 h / 105 °C 3.2: pH 4 4.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane / 1.5 h / 90 - 95 °C 5.1: hydrogenchloride / 1,4-dioxane; 1,2-dimethoxyethane / 2 h 6.1: water; dimethyl sulfoxide; acetonitrile
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; diisopropylamine / chloroform / 1 h / -5 - 0 °C 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 3.1: potassium <i>tert</i>-butylate / isopropyl alcohol / 2.5 h / 105 °C 3.2: pH 4 4.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane / 1.5 h / 90 - 95 °C 5.1: hydrogenchloride / 1,4-dioxane; 1,2-dimethoxyethane / 2 h 6.1: water; dimethyl sulfoxide; acetonitrile

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

33
[ 953039-10-6 ]
[ 953040-09-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

34
[ 953039-10-6 ]
[ 953039-87-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: N-Bromosuccinimide / chloroform

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

35
[ 953039-10-6 ]
[ 953039-88-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-chloro-succinimide / chloroform / 2 h / 40 °C 2: N-Bromosuccinimide / chloroform 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

36
[ 953039-10-6 ]
[ 953039-18-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide; diisopropylamine / chloroform / 1 h / -5 - 0 °C 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

37
[ 953039-10-6 ]
[ 953040-04-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide / 0.5 h / 0 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

38
[ 858452-80-9 ]
[ 953039-10-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 1.35 h / 0 - 145 °C / Neat (no solvent) 2.1: boron tribromide / dichloromethane / 22 h / -10 - 20 °C 2.2: 1 h / 0 °C
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 1.35 h / 0 - 145 °C / Neat (no solvent) 2.1: boron tribromide / dichloromethane / 22.58 h / -5 - 20 °C 2.2: 0.5 h / 0 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

39
[ 53055-05-3 ]
[ 953039-10-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: hydrogenchloride; iron; acetic acid / ethanol / 0.33 h / 0 °C / Heating / reflux 2.1: 1-methyl-pyrrolidin-2-one / ammonium acetate / 0.75 - 1 h / 160 °C 3.1: trichlorophosphate / 1.35 h / 0 - 145 °C / Neat (no solvent) 4.1: boron tribromide / dichloromethane / 22 h / -10 - 20 °C 4.2: 1 h / 0 °C
	Multi-step reaction with 4 steps 1.1: hydrogenchloride; iron; acetic acid / ethanol / 0.33 h / 0 °C / Heating / reflux 2.1: 1-methyl-pyrrolidin-2-one / ammonium acetate / 0.75 - 1 h / 160 °C 3.1: trichlorophosphate / 1.35 h / 0 - 145 °C / Neat (no solvent) 4.1: boron tribromide / dichloromethane / 22.58 h / -5 - 20 °C 4.2: 0.5 h / 0 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

40
[ 70127-96-7 ]
[ 953039-10-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 1-methyl-pyrrolidin-2-one / ammonium acetate / 0.75 - 1 h / 160 °C 2.1: trichlorophosphate / 1.35 h / 0 - 145 °C / Neat (no solvent) 3.1: boron tribromide / dichloromethane / 22 h / -10 - 20 °C 3.2: 1 h / 0 °C
	Multi-step reaction with 3 steps 1.1: 1-methyl-pyrrolidin-2-one / ammonium acetate / 0.75 - 1 h / 160 °C 2.1: trichlorophosphate / 1.35 h / 0 - 145 °C / Neat (no solvent) 3.1: boron tribromide / dichloromethane / 22.58 h / -5 - 20 °C 3.2: 0.5 h / 0 °C

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/117607, 2007, A2

41
[ 953039-10-6 ]
[ 220650-54-4 ]
C₂₁H₃₃ClN₂O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentan-1-ol With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 0.0833333h; Stage #2: 2-chloro-8-hydroxyquinazoline In tetrahydrofuran for 16h;	1.D Step D: Preparation of mt 1. id A solution containing 2.0 g (7.74 mmol) of triphenylphosphine in 30 mLwas treated drop wise with 1.5 mL (7.74 mmol) of diisopropyl azodicarboxylate and the reaction was stirred for 10 minutes. A solution of 3.8 g (15.5 mmol) 5-((tert-butyldimethylsilyl)oxy)-3,3- dimethylpentan- 1-olin 5 mL of THF was added and the resulting reaction was stirred for 5 minutes before the addition of 929 mg (5.16 mmol) 2-chloro-8-hydroxyquinazoline. The reaction was stirred over 16h then the solvents were evaporated. The residue was then chromatographed (40 gram silica column; 0% to 100% EtOAc / Hexanes) to provide the desired compound Tnt 2.ld which was used directly in the next reaction. LCMS (M+H) = 409.

Reference： [1]Current Patent Assignee: SILVERBACK THERAPEUTICS INC - WO2019/79357, 2019, A1 Location in patent: Paragraph 0383

42
[ 953039-10-6 ]
3-(aminomethyl)-6-((8-((5-hydroxy-3,3-dimethylpentyl)oxy)quinazolin-2-yl)amino)benzo[c][1,2]oxaborol-1(3H)-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.08 h 1.2: 16 h 2.1: toluene-4-sulfonic acid / toluene / 16 h / 100 °C 3.1: ammonium hydroxide; hydrogen / water; methanol / 16 h / 20 °C / 2585.81 Torr

Reference： [1]Current Patent Assignee: SILVERBACK THERAPEUTICS INC - WO2019/79357, 2019, A1

43
[ 953039-10-6 ]
C₂₄H₂₃N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 17 h / 60 °C 2: isopropyl alcohol / 16 h / 100 °C / Sealed tube 3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 16 h / 40 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SILVERBACK THERAPEUTICS INC - WO2019/79357, 2019, A1

44
[ 953039-10-6 ]
C₂₃H₂₇BN₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.08 h 1.2: 16 h 2.1: toluene-4-sulfonic acid / toluene / 16 h / 100 °C

Reference： [1]Current Patent Assignee: SILVERBACK THERAPEUTICS INC - WO2019/79357, 2019, A1

45
[ 953039-10-6 ]
[ 1119-51-3 ]
C₁₃H₁₃ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 17h;	2.1.B Step B: Preparation of mt 2.1b A mixture containing 500 mg (2.79 mmol) 2-chloro-8-hydroxyquinazoline in 8 mL of DMF was treated with 771 mg (5.58 mmol) of K2C03, 623 mg (4.18 mmol) of 5-bromo-1- pentene and 72 mg (0.20 mmol) of tetrabutylammonium iodide and the reaction was heated to 60°C for 16h. The reaction was cooled and quenched with water then extracted three times with EtOAc. The combined organic extracts were dried and concentrated. Silica gel chromatography (12g ISCO gold; 0% to 100% EtOAc /Hexanes) provided the desired compound Tnt 2.lb as a white solid.

Reference： [1]Current Patent Assignee: SILVERBACK THERAPEUTICS INC - WO2019/79357, 2019, A1 Location in patent: Paragraph 0388

46
[ 953039-10-6 ]
2-(4-(6-phenylpyrimidin-4-yl)piperazin-1-yl)quinazolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 20 h / 90 °C 2: hydrogenchloride / isopropyl alcohol; ethanol / 4 h / Reflux 3: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 1 h / 0 - 20 °C 4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol; water / 16 h / 110 °C / Inert atmosphere

Reference： [1]Sharma, Vijay Kumar; Barde, Anup; Rattan, Sunita [Synthetic Communications, 2020, vol. 50, # 19, p. 2962 - 2968]

47
[ 953039-10-6 ]
2-(4-(6-(2-(tert-butyl)pyridin-4-yl)pyrimidin-4-yl)piperazin-1-yl)quinazolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 20 h / 90 °C 2: hydrogenchloride / isopropyl alcohol; ethanol / 4 h / Reflux 3: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 1 h / 0 - 20 °C 4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol; water / 16 h / 110 °C / Inert atmosphere

Reference： [1]Sharma, Vijay Kumar; Barde, Anup; Rattan, Sunita [Synthetic Communications, 2020, vol. 50, # 19, p. 2962 - 2968]

48
[ 953039-10-6 ]
2-(4-(6-(quinolin-4-yl)pyrimidin-4-yl)piperazin-1-yl)quinazolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 20 h / 90 °C 2: hydrogenchloride / isopropyl alcohol; ethanol / 4 h / Reflux 3: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 1 h / 0 - 20 °C 4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol; water / 16 h / 110 °C / Inert atmosphere

Reference： [1]Sharma, Vijay Kumar; Barde, Anup; Rattan, Sunita [Synthetic Communications, 2020, vol. 50, # 19, p. 2962 - 2968]

49
[ 953039-10-6 ]
[ 57260-71-6 ]
tert-butyl 4-(8-hydroxyquinazolin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 90℃; for 20h;	Step-1 Synthesis of tert-butyl 4-(8-hydroxyquinazolin-2-yl)piperazine-1-carboxylate (A) To a solution of tert-butyl piperazine-1-carboxylate (2) (2.7 mmol, 1 mol. equiv.) in propan-2-ol (10 mL ) at 0 °C. N,N-diisopropylethylamine (8.1 mmol, 3 mol. equiv.) was added dropwise and allowed to stir for 10 min at same temperature. 2-chloroquinazolin-8-ol (1) (2.7 mmol, 1mol. equiv.) was added and reaction mixture was treated under reflux conditions for 20 h. TLC (40 % ethyl acetate: hexane) showed that starting material was consumed. After completion, reaction mixture was allowed to come to ambient temperature to form a suspension. Solid was filtered, washed twice with propan-2-ol (5 mL) and dried at 55 °C under vacuum for 3 h to afford desired compound. Yield-80%; Off white solid; Melting range: 115.7-117.2 °C; LC-MS (ESI) m/z calculated for C17H22N4O3 (M+H)+ :331.2; found: 331.3 along with (M-56)+ : 275.3; UPLC-99.06%; HPLC-99.82% 1H NMR (400 MHz, DMSO-d6): δ 9.20 (s, 1H), 9.17 (s, 1H), 7.29 (dd, J = 1.75, 7.45 Hz, 1H), 7.11 (m, 2H), 3.92 (m., 4H), 3.43 (m, 4H), 1.44 (s, 9H); 1H NMR (400 MHz, DMSO-d6 + D2O): 9.16 (s, 1H), 7.29 (d, J = 7.02 Hz, 1H), 7.14-7.08 (m, 2H), 3.90 (m., 4H), 3.42 (m., 4H), 1.42 (s, 9H) 13C NMR (101 MHz, DMSO-d6): δ 161.7, 157.7, 154.0, 150.5, 142.0, 122.9, 119.6, 117.5, 115.4, 79.0, 43.5, 43.5, 43.5, 43.5, 28.1, 28.1, 28.1. Anal. calcd. for C17H22N4O3: C, 61.80; H, 6.71; N, 16.96; found: C, 61.88; H, 6.73; N, 17.02

Reference： [1]Sharma, Vijay Kumar; Barde, Anup; Rattan, Sunita [Synthetic Communications, 2020, vol. 50, # 19, p. 2962 - 2968]

50
[ 953039-10-6 ]
[ 109384-19-2 ]
[ 953039-49-1 ]

Yield	Reaction Conditions	Operation in experiment
21%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 1.5h; Inert atmosphere;

Reference： [1]Wellaway, Christopher R.; Baldwin, Ian R.; Bamborough, Paul; Barker, Daniel; Bartholomew, Michelle A.; Chung, Chun-Wa; Dümpelfeld, Birgit; Evans, John P.; Fazakerley, Neal J.; Homes, Paul; Keeling, Steven P.; Lewell, Xiao Q.; McNab, Finlay W.; Morley, Joanne; Needham, Deborah; Neu, Margarete; Van Oosterhout, Antoon J. M.; Pal, Anshu; Reinhard, Friedrich B. M.; Rianjongdee, Francesco; Robertson, Craig M.; Rowland, Paul; Shah, Rishi R.; Sherriff, Emma B.; Sloan, Lisa A.; Teague, Simon; Thomas, Daniel A.; Wellaway, Natalie; Wojno-Picon, Justyna; Woolven, James M.; Coe, Diane M. [Journal of Medicinal Chemistry, 2022, vol. 65, # 1, p. 633 - 664]

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P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
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

[ CAS No. 953039-10-6 ] {[proInfo.proName]}

Quality Control of [ 953039-10-6 ]

Related Doc. of [ 953039-10-6 ]

Product Details of [ 953039-10-6 ]

Safety of [ 953039-10-6 ]

Application In Synthesis of [ 953039-10-6 ]

[ 953039-10-6 ] Synthesis Path-Downstream 1~50

Related Functional Groups of [ 953039-10-6 ]

Chlorides

Alcohols

Related Parent Nucleus of [ 953039-10-6 ]

Quinazolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 953039-10-6 ]

Related Parent Nucleus of
[ 953039-10-6 ]