192570-33-5|5-Fluoroquinazoline-2,4(1H,3H)-dione| Ambeed

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Quality Control of [ 192570-33-5 ] Purity: 95% SDS Specification

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Product Details of [ 192570-33-5 ]

CAS No. :	192570-33-5
Formula :	C₈H₅FN₂O₂
M.W :	180.14
SMILES Code :	FC1=C2C(=O)NC(=O)NC2=CC=C1
MDL No. :	MFCD09954841
InChI Key :	WPPSJUCAPOKSHS-UHFFFAOYSA-N
Pubchem ID :	643346

Safety of [ 192570-33-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 192570-33-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	45.15
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	65.72 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.81
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.78
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.44
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.62
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.87
Solubility	2.45 mg/ml ; 0.0136 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.49
Solubility	5.81 mg/ml ; 0.0322 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.42
Solubility	0.0683 mg/ml ; 0.000379 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.02 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.88

Application In Synthesis of [ 192570-33-5 ]

* 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 [ 192570-33-5 ]

[ 192570-33-5 ] Synthesis Path-Downstream 1~28

1
Hoffer's chlorosugar [ No CAS ]
[ 192570-33-5 ]
[ 192570-36-8 ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

2
[ 434-76-4 ]
[ 57-13-6 ]
[ 192570-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	In neat (no solvent); at 150℃;	General procedure: 5.2.1.1 Quinazoline-2,4(1H,3H)-dione (2a) The mixture of 2-amino-benzoic acid (5 g, 36.46 mmol) and urea (50 g, 83.25 mmol) was stirred at 150 C for 7 h. The reaction mixture was cooled to 100 C and then water (50 mL) was added to quench the reaction. The crude product was obtained by filtration, then dissolved in NaOH aq (6 M, 500 mL). The pH was adjusted to 3 and a precipitate was formed. After filtration and dried under vacuum condition, compound 2a was obtained as white solid (4.5 g, 76.1%); 5.2.1.2 5-Fluoroquinazoline-2,4(1H,3H)-dione (2b) Following the preparation protocol of Section 5.2.1.1 , starting from 2-amino-6-fluorobenzoic acid (2 g, 12.9 mmol), the title compound 2b was obtained as white solid (738 mg, 31.8%); mp >250 C; 1H NMR (300 MHz, DMSO-d6) δ (ppm): 11.27 (s, 1H), 11.25 (s, 1H), 7.60 (dt, J1 = 8.4 Hz, J2 = 5.7 Hz, 1H), 6.88-6.99 (m, 2H); HR-MS (ESI): m/z, Calcd for C8H6N2O2F [M+H]+ 181.0408, Found: 181.0404.

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.
[2]Russian Chemical Bulletin,2007,vol. 56,p. 1821 - 1827.
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 681 - 693.

3
[ 192570-33-5 ]
[ 87611-00-5 ]

Yield	Reaction Conditions	Operation in experiment
80.8%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; trichlorophosphate; In toluene; at 50 - 120℃;	B-1 (2.6 g, 14.43 mmol) was suspended in 29 mL of toluene and heated to 50 C. Phosphoryl chloride (9.88 mL, 108.25 mmol) was added dropwise, and then DBU (4.31 mL, 28.87 mmol) was added dropwise. The mixture was stirred vigorously at 120 C for overnight. After the reaction mixture was cooled at room temperature, it was added dropwise to ice-water. The aqueous layer was extracted with ethyl acetate. After it was washed with brine and dried with Na2S04, it was concentrated to give a solid. The crude product was purified by column chromatography on silica gel eluting with toluene to yield 3.41 g (80.8%) of B-2 as a white powder. It was used for next reaction without purification.

References: [1]Patent: WO2017/109722,2017,A1 .Location in patent: Paragraph 0449.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 2297 - 2300.

4
[ 192570-33-5 ]
[ 769158-32-9 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2297 - 2300.

5
[ 192570-33-5 ]
[ 769158-33-0 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2297 - 2300.

6
[ 192570-33-5 ]
C₂₁H₂₀FN₅O [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2297 - 2300.

7
[ 77326-36-4 ]
[ 192570-33-5 ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

8
[ 192570-33-5 ]
1-{2-deoxy-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl}-5-fluoro-quinazoline-2,4(3H)-dione [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

9
[ 192570-33-5 ]
1-(2-deoxy-α,β-D-erythro-pentofuranosyl)-5-fluoro-quinazoline-2,4(3H)-dione [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

10
[ 192570-33-5 ]
1-(2-deoxy-α-D-erythro-pentofuranosyl)-5-fluoro-quinazoline-2,4(3H)-dione [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

11
[ 192570-33-5 ]
1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-fluoro-quinazoline-2,4(3H)-dione [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

12
[ 192570-33-5 ]
[ 192570-56-2 ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

13
[ 192570-33-5 ]
[ 192570-51-7 ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

14
[ 999-97-3 ]
[ 192570-33-5 ]
5-fluoro-2,4-di(trimethylsilyloxy)quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In toluene;Reflux;	General procedure: 5.2.2.1 1-(3-Nitrobenzyl)quinazoline-2,4(1H,3H)-dione (5a) To a suspension of 2a (140 mg, 0.86 mmol) in toluene (4 mL) and hexamethyldisilazane (HMDS; 347 mg, 2.15 mmol), three drops of sulfuric acid were added with caution. The mixture was heated to reflux and stirred under refluxing for 8 h untill clear solution was obtained. After the removal of toluene and excess HMDS under vacuum distillation, 1-(bromomethyl)-3-nitrobenzene (744 mg, 3.44 mmol) was added to the residue. The reaction mixture was heated to 130 C and was stirred at this temperature for 3 h, the reaction mixture was diluted with 1,4-dioxane (2 mL) at 100 C, and then methanol (3 mL) was added at 70 C for 30 min. The suspension was cooled below 5 C and precipitates were collected by filtriation. After washing with methanol (5 mL) and water (5 mL), the crude product was dried under vacuum condition to afford 5a as white solid (200 mg, 77.3%);
	With sulfuric acid; In toluene; at 108 - 112℃; for 48h;Inert atmosphere; Large scale;	In a reaction kettle, to <strong>[192570-33-5]5-fluoroquinazoline-2,4(1H,3H)-dione</strong> (IV, 4.4 Kg, 24.43 mol) was added toluene (8 times volume of the compound of Formula IV) and then hexamethyldisilazane (HMDS, 61.08 mol). Then sulfuric acid (1.22 mol) was added dropwise. The mixed liquid was heated to 108112 C. for refluxing and stirred for 48 hours until all solids were dissolved. Under nitrogen protection, the reaction liquid was cooled to 5565 C. and concentrated, and then the solid was cooled to 1530 C. in nitrogen atmosphere to provide the target compound 5-fluoro-2,4-di(trimethylsilyloxy)quinazoline IV-TMS as a crude product used for the next step reaction directly. (0123) To 5-fluoro-2,4-di(trimethylsilyloxy)quinazoline IV-TMS was added methyl 5-bromomethyl-2-fluorobenzoate (V, 26.87 mol) and the solvent N,N-dimethylformamide (DMF, 1 time volume of the compound of Formula IV-TMS). The mixture was heated to 105115 C. and stirred for 16 hours, which was sampled and analyzed by HPLC for IPC (IPC limit: IV/III10%, stir another 24 hours). (0124) After the reaction was complete, dioxane with a volume ratio of 1.2 to the compound of Formula IV-TMS was added to the reaction liquid slowly. After the reaction liquid was cooled to 6570 C., 14 MeOH with volume ratio of 3 to the compound of Formula IV-TMS was added dropwise slowly. Then the mixture was stirred at 6570 C. for 0.51 hour. After the reaction was finished, the reaction liquid was cooled to 05 C. and maintained at the above temperature and stirred for 12 hours, and then filtered. The filter cake was washed with MeOH (2 times volume of the compound of Formula IV-TMS) and water (4 times volume of the compound of Formula IV-TMS). The filter cake was dried under vacuum at 4045 C. to provide 6.9 Kg of the target compound 15 5-fluoro-1-(4-fluoro-3-methoxycarbonylbenzyl)quinazoline-2,4(1H,3H)-dione (III, yield: 74.6%) as a white solid. HPLC (std): 8.49 min; KF: 0.21%; Residue on ignition: 0.02%; GC (residual solvent): MeOH 0.06%; Dioxane 0.07%; N,N-Dimethylformamide 0.37%.

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 681 - 693.
[2]Patent: US2019/112298,2019,A1 .Location in patent: Paragraph 0121-0124.
[3]Patent: WO2022/100577,2022,A1 .Location in patent: Page/Page column 20.

15
[ 124-38-9 ]
[ 77326-36-4 ]
[ 192570-33-5 ]

References: [1]RSC Advances,2016,vol. 6,p. 111079 - 111089.

16
[ 77326-36-4 ]
[ 33513-42-7 ]
[ 192570-33-5 ]

References: [1]Organic Process Research and Development,2016,vol. 20,p. 2067 - 2073.

17
[ 192570-33-5 ]
C₁₄H₈ClFN₂O [ No CAS ]

References: [1]Patent: WO2017/109722,2017,A1 .

18
[ 192570-33-5 ]
2-chloro[1]benzopyrano[4,3,2-de]quinazoline [ No CAS ]

References: [1]Patent: WO2017/109722,2017,A1 .

19
[ 192570-33-5 ]
C₄₂H₂₃N₃O [ No CAS ]

References: [1]Patent: WO2017/109722,2017,A1 .

20
[ 434-76-4 ]
[ 917-61-3 ]
[ 192570-33-5 ]

Yield	Reaction Conditions	Operation in experiment
91.5%		2-Amino-6-fluorobenzoic acid (35 g, 225.6 mmol) was dissolved in 885 ml of water and 26 mL of acetic acid. The mixture was stirred at 35 C for 15 min. After that, sodium cyanate (36.67 g, 564 mmol) dissolved in 442 mL of water was added dropwise to the suspension, and the mixture was stirred at 35 C for 30 min. Then, sodium hydroxide (180.49 g / 4.51 mol) was slowly added to the reaction mixture, the mixture was cooled at room temperature. After 374 mL of hydrogen chloride was added there, the precipitate was collected by filtration and washed with water. The solid was dried in a vacuum oven to yield 37.19 (91.5%) of B-1 as white solid. LC-MS (m/z): 180

References: [1]Patent: WO2017/109722,2017,A1 .Location in patent: Paragraph 0449.

21
methyl (6-fluoro-2-nitrobenzoyl)carbamate [ No CAS ]
[ 192570-33-5 ]

Yield	Reaction Conditions	Operation in experiment
75.3%	With palladium 10% on activated carbon; p-toluenesulfonic acid monohydrate; hydrogen; In methanol; at 20℃; for 3h;	General procedure: To a magnetically stirred solution of 2a (200 mg, 0.892 mmol) in CH3OH (50 mL) was added 10% Pd/C (10% Pd loaded on Carbon wetted with ca. 55% water, 20 mg) and PTSA · H2O (8.6 mg, 0.045 mmol). The reaction mixture was stirred under an atmosphere of hydrogen at room temperature for 3 h. After filtration of Pd/C and concentration under reduced pressure at 45 C, 20 mL H2O was added to the residue and the mixture was stirred at 0 C for 1 h.

References: [1]Synthetic Communications,2018,vol. 48,p. 1183 - 1189.

22
[ 434-76-4 ]
[ 192570-33-5 ]

References: [1]Patent: US2019/112298,2019,A1 .

23
C₈H₇FN₂O₃ [ No CAS ]
[ 192570-33-5 ]

References: [1]Patent: US2019/112298,2019,A1 .

24
C₈H₄FN₂O₂^(1-)*Na⁽¹⁺⁾ [ No CAS ]
[ 192570-33-5 ]

Yield	Reaction Conditions	Operation in experiment
6.1 kg	With acetic acid; In water; at 85 - 95℃; for 2h;pH 5 - 6;Large scale;	In a reaction kettle, to 2-amino-6-fluorobenzoic acid (B, 6.0 Kg, 38.68 mol) was added water (35 times volume of the compound of Formula B), then acetic acid (46.42 mol) was added, and the mixture was stirred at 515 C. for 2030 min. At the maintained temperature of 515 C., the solution of KOCN (46.42 mol) dissolved in water (2.5 times volume of the compound of Formula B) was added to the above mixed liquid dropwise, and the mixture was stirred at 515 C. for 1 hour, which was sampled and analyzed by HPLC for IPC (IPC limit: B/IV-A2% stir another 12 hour until the limit was reached) and found to meet the limit (B/IV-A=0.7%). After the reaction was complete, 3N aqueous NaOH solution (NaOH (299.77 mol) dissolved in water (3 times volume of the compound of Formula B)) was added to the reaction mixture dropwise at a temperature below 0 C., and stirred at 1025 C. for another 1620 hours. The mixture was sampled and analyzed by HPLC for IPC (IPC limit IV-A/IV-B2% stir another 48 hours) and found to meet the limit (IV-A/IV-B=0.3%). After the reaction was complete, the reaction liquid was cooled to 05 C. and stirred for another 24 hours, which was sampled and analyzed by HPLC for IPC (IPC limit: residual of the target compound IV in mother liquid 0.5% stir another 12 hours). After the reaction was finished, the mixture was filtered and the filter cake was washed with 05 C. water (13 times volume of the compound of Formula B). The obtained filter cake was put in another reaction kettle, to which water (the volume ratio of water to the compound of Formula B was 30) was added, the mixture was heated to 8595 C., and maintained at the temperature and stirred for 2 hours. The pH value of the reaction liquid was adjusted to 56 with acetic acid (119.91 mol), and the mixture was maintained at the temperature of 8595 C. and stirred for 2 hours. Then the reaction liquid was cooled to 05 C. and stirred for 24 hours, which was sampled and analyzed, by HPLC for IPC (residual, of the target compound IV in mother liquid 0.5% stir another 12 hours). After the reaction was finished, the mixture was filtered and the filter cake was washed with water (5 times volume of the compound of Formula B) and dried under vacuum at 4550 C. for 16 hours to provide 6.1 Kg of the target compound 5-fluoroquinazoline-2,4(1H,3H)-dione (IV, HPLC, purity: 98.9%, yield: 86.9%) as an off-white solid. HPLC (std): 6.28 min; 1H NMR (400 MHz, DMSO-d6): δ 11.25 (s, 2H), 7.59 (dd, J=13.8, 8 Hz, 1H), 6.96 (d, J=8 Hz, 1H), 6.91 (dd, J=11.4, 8.4 Hz, 1H); KF: 0.4%.

References: [1]Patent: US2019/112298,2019,A1 .Location in patent: Paragraph 0119-0120.

25
[ 192570-33-5 ]
5-((5-fluoro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl)-2-fluorobenzoic acid methyl ester [ No CAS ]

References: [1]Patent: US2019/112298,2019,A1 .
[2]Patent: WO2022/100577,2022,A1 .

26
[ 192570-33-5 ]
[ 1401683-99-5 ]

References: [1]Patent: US2019/112298,2019,A1 .
[2]Patent: WO2022/100577,2022,A1 .

27
[ 192570-33-5 ]
[ 1401682-78-7 ]

References: [1]Patent: US2019/112298,2019,A1 .
[2]Patent: WO2022/100577,2022,A1 .

28
[ 192570-33-5 ]
2-chloro-5-fluoroquinazolin-4-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53 mg		General procedure: According to a modified, previous described procedure (Keov, P. et al, Neuropharmacology 2011, 60, 24- 35), the anthranilic acid A (1 eq.) was added portion wise to melted urea (10 eq.) and the mixture was stirred at 150 C for 16 h. After cooling to room temperature, water was added and the mixture was sonicated for 30 min to get a finely dispersed precipitate, which was collected by suction filtration, washed several times with water and dried in vacuo. The obtained quinazoline- 2,4(lA/,3A/)-dione B (1 eq.) was suspended in POCh (~0.5 mL/mmol) at room temperature, and A/A-di methyl ani 1 i ne (cat. amounts, 2-3 drops) was added. After the reaction mixture was stirred at 120 C for 16 h, it was cooled to room temperature and poured carefully on ice. The formed precipitate was collected by suction filtration, washed several times with water and was directly dissolved in THF (2-3 mL/mmol). Aqueous ammonia (25%, 1-2 mL/mmol) was added and the reaction mixture was stirred for 2 h at room temperature. After removal of THF under reduced pressure the aqueous solution was lyophilized to obtain the 2-chloroquinazolin-4-amine C, which was used in the next step without further purification, otherwise it is indicated below.

References: [1]Patent: WO2019/204768,2019,A1 .Location in patent: Paragraph 0338; 0342; 0344; 0345.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Precautionary Statements-General
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P222	Do not allow contact with air.
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P230	Keep wetted
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P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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

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CAS No.: 192570-33-5

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CAS No.: 192570-33-5

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[ 192570-33-5 ] Synthesis Path-Downstream 1~28

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