[ CAS No. 62882-11-5 ] {[proInfo.proName]}

Name: 62882-11-5|4-(Oxazol-2-yl)aniline|98%
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Quality Control of [ 62882-11-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 62882-11-5 ]

CAS No. :	62882-11-5	MDL No. :	MFCD11040381
Formula :	C₉H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SLLOVNWUCAZDJC-UHFFFAOYSA-N
M.W :	160.17	Pubchem ID :	12371739
Synonyms :

Calculated chemistry of [ 62882-11-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.34
TPSA :	52.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	1.93
Log Po/w (MLOGP) :	0.71
Log Po/w (SILICOS-IT) :	1.73
Consensus Log Po/w :	1.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.28
Solubility :	0.846 mg/ml ; 0.00528 mol/l
Class :	Soluble
Log S (Ali) :	-2.01
Solubility :	1.55 mg/ml ; 0.00968 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.38
Solubility :	0.066 mg/ml ; 0.000412 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 62882-11-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 62882-11-5 ]

* 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 [ 62882-11-5 ]

[ 62882-11-5 ] Synthesis Path-Downstream 1~25

1
[ 62882-11-5 ]
[ 121-60-8 ]
[ 860542-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Rosenbaum; Cass [Journal of the American Chemical Society, 1942, vol. 64, p. 2444]

2
[ 62882-11-5 ]
[ 20662-88-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite anschliessend Behandeln mit H₃PO₄;

Reference： [1]Rosenbaum; Cass [Journal of the American Chemical Society, 1942, vol. 64, p. 2444]

3
[ 62882-08-0 ]
[ 62882-11-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogen In methanol	115.b A solution of 2-(4-nitro-phenyl)-oxazole (400mg, 2. lmmol) in methanol (1 OmI) was hydrogenated over 10% Pd/C at 30 psi until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to give a residue which was purified by column chromatography using ethyl acetate/ pet ether (3:7) to yield 4- oxazol-2-yl-phenylamine (300mg, 89%).
	With ethanol; nickel Hydrogenation;
	With hydrogenchloride; tin(ll) chloride

	With hydrogen In ethanol; ethyl acetate	1 1.268 g of 1-(2-oxazole)-4-nitro-benzene in 100 ml ethanol and 50 ml ethyl acetate was reduced at normal pressure in the presence of palladium/carbon (10%) with a balloon filled with hydrogen. No starting material was left after hydrogenation was conducted overnight, as shown by TLC. Catalyst was filtered off, and the filtrate was concentrated by evaporation in a vacuum to yield 1.017 g of product as an off-white powder. 1H-NMR (CDCl3), δ 7.83(d, 2H), 7.62(s, 1H), 7.15(s, 1H), 6.77(d, 2H), 3.92(b, 2H). MS (ei): M(+)+H=161
	With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 4h;	Synthesis of 4-(oxazol-2-yl) aniline. To a solution of commercially available 2-(4-nitrophenyl)oxazole, 1 (1 equiv.) in methanol (0.05 M) was added Pd/C (10% by wt) and stirred reaction at room temperature under H2 gas balloon pressure for 4 h. After completion of starting material, the reaction mixture was filtered through Celite bed and filtrate was concentrated to give 4-(oxazol-2-yl) aniline, 2 as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.0 (s, 1H), 7.64 (d, J=8.4 Hz, 2H), 7.20 (s, 1H), 6.63- 6.61 (d, J=8.4 Hz, 2H), 5.68 (brs, 2H). LC-MS: m/z 161.0(M+H) with a purity of 97%.

Reference： [1]Current Patent Assignee: F2G LTD - WO2006/123145, 2006, A1 Location in patent: Page/Page column 56
[2]Rosenbaum; Cass [Journal of the American Chemical Society, 1942, vol. 64, p. 2444]
[3]Rosenbaum; Cass [Journal of the American Chemical Society, 1942, vol. 64, p. 2444]
[4]Current Patent Assignee: ROCHE HOLDING AG - US2007/135500, 2007, A1 Location in patent: Page/Page column 8
[5]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2014/189466, 2014, A1 Location in patent: Paragraph 000118

4
[ 62882-11-5 ]
[ 124-38-9 ]
[ 68535-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	(i) aq. NaNO₂, H₂SO₄, (ii) (heating), (iii) /BRN= 1900390/, K₂CO₃; Multistep reaction;

Reference： [1]Jones; Fordice; Greenwald; Hannah; Jacobs; Ruyle; Walford; Shen [Journal of Medicinal Chemistry, 1978, vol. 21, # 11, p. 1100 - 1104]

5
[ 62882-11-5 ]
[ 68535-56-8 ]

Yield	Reaction Conditions	Operation in experiment
	(i) aq. NaNO₂, H₂SO₄, (ii) (heating); Multistep reaction;

Reference： [1]Jones; Fordice; Greenwald; Hannah; Jacobs; Ruyle; Walford; Shen [Journal of Medicinal Chemistry, 1978, vol. 21, # 11, p. 1100 - 1104]

6
[ 62882-11-5 ]
[ 46047-24-9 ]

Yield	Reaction Conditions	Operation in experiment
	(i) HNO₂, (ii) CuCl; Multistep reaction;

Reference： [1]Brown,E.V. [Journal of Organic Chemistry, 1977, vol. 42, p. 3208 - 3209]

7
[ 62882-11-5 ]
[ 372-09-8 ]
2-Cyano-N-(4-oxazol-2-yl-phenyl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl-carbodiimide In tetrahydrofuran Ambient temperature;

Reference： [1]Kuo, Elizabeth A.; Hambleton, Philip T.; Kay, David P.; Evans, Phillip L.; Matharu, Saroop S.; Little, Edward; McDowall, Neil; Jones, C. Beth; Hedgecock, Charles J. R.; Yea, Christopher M.; Chan, A. W. Edith; Hairsine, Peter W.; Ager, Ian R.; Tully, W. Roger; Williamson, Richard A.; Westwood, Robert [Journal of Medicinal Chemistry, 1996, vol. 39, # 23, p. 4608 - 4621]

Yield	Reaction Conditions	Operation in experiment
	p-Nitroverb. mit H2 an Pd/C;
	With hydroxylamine hydrochloride; iron In ethanol; water at 95℃; for 1.5h;	1.16A General Method 9A: Nitro Reduction with Iron/AmmoniumChloride General procedure: [0566] 10 eq. of ammonium chloride were dissolved in anethanol/water mixture (2: 1) (about 2M), the mixture washeated to 95° C. and the nitroaryl compound (1 eq.) wasadded. 3 eq. of iron powder were added in small portions overa period ofl h. The reaction mixture was then stirred at 95° C.for 30 min, and the hot mixture was then filtered throughkieselguhr. The filter cake was washed with ethanol and thefiltrate was freed from ethanol under reduced pressure. Theaqueous phase that remained was extracted three times withdiethyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (sodiumsulphate), filtered and concentrated under reduced pressure.The crude product was then purified either by normal phasechromatography (mobile phase: cyclohexane/ethyl acetatemixtures or dichloromethane/methanol mixtures) or by preparativeRP-HPLC (water/acetonitrile gradient or water/methanol gradient).
	With iron; ammonium chloride In ethanol; water for 2h; Reflux;	53-54.3; 84.3 General procedure: Step 3: General procedure for reduction:[0003001 To a stirred solution of compound 4 (1 eq) in ethanol, iron powder (5 eq), water and ammonium chloride (5 eq) were added slowly. The reaction mixture was heated to reflux for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the title compound 5.[000301j The intermediates listed in the following table were prepared in a similar manner starting with appropriate compound 4.

220 mg

With ammonium chloride In ethanol; water at 95℃; for 1.5h;

1.16A tert-Butyl 4-amino-2-fluorobenzoate General procedure: A solution of 1.109 g (20.73 mmol, 10 eq.) of ammoniumchloride in 6.25 ml of ethanol and 3.125 ml of water was heated to 95 C, and500 mg (2.07 mmol) of tert-butyl 2-fluoro-4-nitrobenzoate were added. 347 mg(6.22 mmol, 3 eq.) of iron powder were added in small portions over 1 h. Thereaction mixture was then stirred at 95 C for 30 min, and the hot mixture wasthen filtered through kieselguhr. The filter cake was washed with ethanol andthe filtrate was freed from ethanol under reduced pressure. The aqueous phasewas extracted three times with in each case 20 ml of diethyl ether. Thecombined organic phases were washed with saturated aqueous sodium chloridesolution, dried (sodium sulphate), filtered and concentrated under reducedpressure. The crude product was purified by normal phase chromatography (mobilephase: cyclohexane/ethyl acetate 30%-50% mixtures). Yield: 280 mg (51% of theory).

9
[ 62882-11-5 ]
(Z)-2-Cyano-3-cyclopropyl-3-hydroxy-N-(4-oxazol-2-yl-phenyl)-acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diisopropylcarbodiimide / tetrahydrofuran / Ambient temperature 2: 1.) NaH / 1.) THF, RT, 2.) THF, RT

10
[ 62882-11-5 ]
sulfanilic acid-(4-oxazol-2-yl-anilide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine 2: aqueous HCl

Reference： [1]Rosenbaum; Cass [Journal of the American Chemical Society, 1942, vol. 64, p. 2444]

11
4-nitro-benzoic acid-(2,2-diethoxy-ethylamide) [ No CAS ]
[ 62882-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: P₂O₅; concentrated H₂SO₄ 2: SnCl₂; concentrated HCl

Reference： [1]Rosenbaum; Cass [Journal of the American Chemical Society, 1942, vol. 64, p. 2444]

12
[ 62882-11-5 ]
C₁₄H₁₂ClF₃O₂ [ No CAS ]
N-(4-oxazol-2-yl-phenyl)-2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 20℃; for 1h;	1 0.052 ml of thionyl chloride was added to a solution of 0.1 g of 2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionic acid in 2 ml of dimethyl acetamide at -5° C., and stirred for 30 min at -5° C. Then 56 mg of 4-oxazol-2-yl-phenylamine was added in solid form and stirred for 1 hour at room temperature. Potassium carbonate was added and stirred overnight at room temperature. The reaction was quenched with water and extracted with ethyl acetate. The combined ethyl acetate extracts were washed twice with water, dried and concentrated by evaporation. The residue was purified by column chromatography on silica-gel (EtOAc-hexane 10%-20%) to yield 63 mg of product. 1H-NMR (CDCl3), δ 8.62(s, 1H), 8.0(d, 2H), 7.7(s, 1H), 7.6(m, 3H), 7.39(t, 1H), 7.27(m, 2H), 3.68(s, 2H), 2.58(m, 4H), 2.16(m, 1H), 1.86(m, 1H). MS (ei): M(+)+H=429, M+-H=427

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2007/135500, 2007, A1 Location in patent: Page/Page column 8

13
[ 391248-21-8 ]
[ 62882-11-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: ethyl 2-(4-aminophenyl)oxazole-4-carboxylate With lithium hydroxide In water; N,N-dimethyl-formamide at 45℃; for 12h; Stage #2: With hydrogenchloride In water Stage #3: With copper(II) oxide In N,N-dimethyl-formamide at 160℃; for 70h;

Reference： [1]Verrier, Cecile; Martin, Thibaut; Hoarau, Christophe; Marsais, Francis [Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7383 - 7386]

14
[ 62882-11-5 ]
[ 652-37-9 ]
2-(1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(4-(oxazol-2-yl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h;	General procedure: To a stirred solution of commercially available 2-(l,3- dimethyl-2,6-dioxo-2,3-dihydro-lH-purin-7(6H)-yl)acetic acid, 1 in dichloromethane (0.1 M) was added the respective amine (100 1 equiv.), EDCI (1.2 equiv.) and HOBT (1.2 equiv.). The reaction mixture was stirred at room temperature for 16 h. After completion of starting material, water was added to the reaction mixture and product was extracted with 10% methanol/chloroform twice. The organic layer was dried over anhydrous Na2S04, concentrated under vacuum to afford the crude product. The crude product is further purified by column chromatography. [000152] Compound 24: 2-(l,3-dimethyl-2,6-dioxo-2,3-dihydro-lH-purin-7(6H)- oxazol-2-yl) phenyl)acetamide. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 10.72 (s, 1H), 8.19 (s, 1H), 8.09 (s, 1H), 7.96-7.94 (d, J = 8.8 Hz, 2H), 7.75-7.72 (d, J = 8.8 Hz, 2H), 7.35 (s, 1H), 5.24 (s, 2H), 3.46 (s, 3H), 3.19 (s, 3H). LC-MS: m/z 379.3 (M+H) with a purity of 96.48 %. HPLC: At 254 nm with a purity of 97%.

Reference： [1]Patent: WO2014/189466,2014,A1 .Location in patent: Paragraph 000151-000152

15
[ 62882-11-5 ]
C₂₂H₂₇ClN₆O₂ [ No CAS ]
6-(1-methyl-3-(2-morpholinoethyl)-1H-indazol-6-yl)-2-morpholino-N-(4-(oxazol-2-yl)phenyl)pyrimidin-4-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(1,3-oxazol-2-yl)aniline; C₂₂H₂₇ClN₆O₂ With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; Inert atmosphere; Stage #2: With hydrogenchloride In methanol at 20℃; for 0.5h;	150-156 [000524j 6-(l-methyl-3-(2-morpholinoethyl)-1H-indazol-6-yl)-2-morpholino-N-(4- (oxazol-2-yl) phenyl) pyrimidin-4-amine General procedure: General Procedure for Buchwald Coupling[000172j A mixture of the intermediate of formula 101 (1 eq) or formula 100, R3NH2 (1 eq) and cesium carbonate (1.5 eq) in 1 ,4-dioxane was taken and purged with argon for 10 mm, followed by the addition of BNAP (0.22 eq) and purged argon for additional 5 mm. Palladium acetate (0.2 eq) was added and stirred at 100 °C for overnight. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated to dryness. The residue was taken in ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to afford a Compound of Formula I or formula 102, respectively.:_[000201j The title compound (crude) has been synthesized by following the General procedure for Buchwald Coupling described above using methyl 5-aminopicolinate 6 and compound 5.:_[000524j 6-(l-methyl-3-(2-morpholinoethyl)-1H-indazol-6-yl)-2-morpholino-N-(4- (oxazol-2-yl) phenyl) pyrimidin-4-amine: The title compound has been synthesized by following the general procedure described above for Buchwald coupling by using chloro compound 1 and aniline. The compound was taken in methanol (3 mE), methanol HC1( 1.5 mL) was added and stirred at rt for 30 mm. The reaction mixture was evaporated under reduced pressure to afford title compound as HC1 salt. ‘H NMR (400 MHz, DMSO-d6) ö 11.11 (s, 1H), 8.23 (s, 1H), 8.18 (s, 1H), 8.01 -7.86 (m, 5H), 7.74 (d, J= 8.4 Hz, 1H), 7.35 (s, 1H), 6.82 (s, 1H), 4.10 (s, 3H), 4.06-3.98 (m, 2H), 3.84 (d, J= 11.9Hz, 8H), 3.76 (q, J= 7.3, 4.8 Hz, 6H),

Reference： [1]Current Patent Assignee: BIOMARIN PHARMACEUTICAL INC - WO2016/57834, 2016, A1 Location in patent: Paragraph 000172; 000524

16
[ 62882-11-5 ]
2,4-dimethylpyrrolo[1,2-a]pyrimidine-8-carboxylic acid [ No CAS ]
2,4-dimethyl-N-(4-(1,3-oxazol-2-yl)phenyl)pyrrolo[1,2-a]pyrimidine-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With HATU; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 16h;	9 EXAMPLE 9 - PREPARATION OF 2,4-DIMETHYL-N-(4-(1,3-OXAZOL-2-YL)PHENYL) PYRROLO[1,2-A] PYRIMEDINE-8-CARBOXAMEDE [00221] To a stirring solution of 2,4-dimethylpyrrolo[l,2-a]pyrimidine-8-carboxylic acid 3 (38 mg, 0.2 mmol), HATU (152 mg, 0.4 mmol), and DIPEA (103 mg, 0.8 mmol) in 1 mL of DMF was added 4-(oxazol-2-yl)aniline (38.4 mg, 0.24 mmol). The reaction mixture was stirred at 60 °C for 16 hours, cooled and filtered. The resulting solid was washed with H20, DCM and diethyl ether, and dried in vacuo to give the title compound (18 mg, 27%) as a yellow solid. XH NMR (400 MHz, DMSO-i) δ 11.02 (s, IH), 8.19 (s, IH), 7.98 (d, J= 8.8 Hz, 2H), 7.92 (d, J = 8.8 Hz, 2H), 7.50 (d, J= 3.2 Hz, IH), 7.39 (d, J= 2.8 Hz, IH), 7.36(s, IH), 6.93 (s, IH), 2.67 (s, 6H).ES-MS m/z: 333.1 [M+H+]. HPLC Purity (214 nm): > 99%; tR= 9.94 min.

Reference： [1]Current Patent Assignee: BIAL R D INVESTMENTS - WO2016/73891, 2016, A1 Location in patent: Paragraph 00221

17
[ 62882-11-5 ]
[ 32704-61-3 ]
2,4-dimethyl-N-(4-(oxazol-2-yl)phenyl)imidazo[1,5-a]pyrimidine-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(1,3-oxazol-2-yl)aniline With trimethylaluminum In toluene at 0℃; for 0.5h; Stage #2: ethyl 2,4-dimethylimidazo[1,5-a]pyrimidine-8-carboxylate In toluene at 0 - 100℃; for 14.1667h;	8 EXAMPLE 8- PREPARATION OF 2,4-DIMETHYL-N-(4-(OXAZOL-2-YL)PHENYL)IMIDAZO[1,5- a]PYRIMIDINE-8-CARBOXAMIDE EXAMPLE 8- PREPARATION OF 2,4-DIMETHYL-N-(4-(OXAZOL-2-YL)PHENYL)IMIDAZO[1,5- a]PYRIMIDINE-8-CARBOXAMIDE A solution of 4-(oxazol-2-yl)aniline (80 mg, 0.54 mmol) in toluene (4 mL) at 0C was charged with 2M solution of trimethyl aluminum in toluene (0.9 mL, 1.60 mmol) and stirred at 0C for 30 min. To the resulting mixture was added a solution of ethyl 2,4- dimethylimidazo[1,5-a]pyrimidine-8-carboxylate 2 (100 mg, 0.45 mmol) in toluene (1 mL) and stirred for 10 min. Then, the reaction mixture was heated to 100C for 14 h. Next, the reaction mixture was quenched with 1N HCl and extracted with DCM (2 x 10 mL) to obtain crude compound. The crude compound was purified by FCC (eluent, 1% methanol in DCM) to afford the title compound as a yellow solid (25 mg, 16%).1H NMR (400 MHz, DMSO-d6) δ 10.04 (s, 1H), 8.04 (d, J=8.9 Hz, 2H), 8.00 (d, J=8.8 Hz, 1H), 7.90 (d, J=8.9 Hz, 2H), 7.69 (s, 1H), 7.22 (d, J=8.8 Hz, 1H), 6.56 (s, 1H), 2.68 (s, 6H). ES-MS m/z 333.35 (M+H)+. HPLC purity 92.5%.

Reference： [1]Current Patent Assignee: BIAL R D INVESTMENTS - WO2016/73889, 2016, A1 Location in patent: Paragraph 00211

18
[ 555-16-8 ]
[ 62882-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sulfuric acid / water / 2 h / 20 °C 1.2: 0.5 h / 180 °C 2.1: hydrogen / palladium 10% on activated carbon / methanol / 1551.49 Torr

Reference： [1]Current Patent Assignee: F2G LTD - WO2006/123145, 2006, A1

19
[ 62882-11-5 ]
[ 77718-46-8 ]
2-hydroxy-5-(N-(4-(oxazol-2-yl)phenyl)sulfamoyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88 mg	With pyridine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	38 Example 38 2-Hvdroxy-5-(N-(4-(oxazol-2-yl)phenyl)sulfamoyl)benzamide To a solution of 4-(oxazol-2-yl)aniline (200 mg) in DCM (10 mL) at 0 °C was added pyridine (0.631 mL) followed by 3-carbamoyl-4-hydroxybenzene-1 -sulfonyl chloride (lnt-1 , 368 mg). The reaction mixture was allowed to warm to RT and stirred for 16 hr. The reaction mixture was diluted with water (15 mL) and filtered to obtain the crude product. The crude product was purified by preparative reversed phase HPLC (Xterra C18, 19x250 mm) using a gradient of 16-98% acetonitrile in 10 mM ammonium bicarbonate (aq). The desired fractions were concentrated under reduced pressure to afford the titled compound (88 mg). LCMS m/z 359.97 (M+H)+. NMR (400 MHz, DMSO-c/6) δ ppm 7.05 (d, J=8.77 Hz, 1 H) 7.16 - 7.38 (m, 3 H) 7.73 - 7.95 (m, 3 H) 8.04 (br. s., 1 H) 8.14 (s, 1 H) 8.42 (d, J=1 .75 Hz, 1 H) 8.59 (br. s., 1 H) 10.55 (br. s., 1 H) 13.50 (br. s., 1 H).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2017/153952, 2017, A1 Location in patent: Page/Page column 122

20
[ 62882-11-5 ]
(R)-(5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrobenzofuro[5,4-d]thiazol-7-yl)methyl carbonochloridate [ No CAS ]
(R)-(5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrobenzofur [5,4-d]thiazol-7-yl)methyl (4-(oxazol-2-yl)phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With pyridine; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.833333h;	207 EXAMPLE 207(R)-(5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrobenzofuro [5 ,4-djthiazol-7-yl)methyl (4-(oxazol-2-yl)phenyl)carbamate 4-(Oxazol-2-yl)aniline (15.67 mg, 0.098 mmol) was dissolved in DCM (1.0 mL) along with pyridine (0.021 mL, 0.261 mmol) and DIEA (0.017 mL, 0.098 mmol). Intermediate 14SF (15 mg, 0.033 mmol) in 2 mL of DCM was added dropwise, and the reaction mixture was stirred at room temperature for 50 minutes. The reaction was quenched with 1.0 N HC1 (0.5 mL). All solvent was removed under vacuum. The crudewas dissolved in DMSO/THF (2:1, 6 mL) and purified via preparative LC/MS (method C,55-100% B over 20 mm, then a 5-mm hold at 100% B). Fractions containing the desired product were combined and dried via centrifugal evaporation to yield Example 207 (7.5 mg, 39% yield). ‘H NMR (500MHz, DMSO-d6) 8.72 (s, 1H), 8.57 (d, J1.5 Hz, 1H), 8.15-8.10 (m, 1H), 7.90-7.85 (m, 3H), 7.81 (s, 2H), 7.62 (br. s., 1H), 7.33-7.28 (m, 1H),5.48-5.40 (m, 1H), 4.55 (dd, J=12.4, 2.6 Hz, 1H), 4.42 (dd, J=12.4, 6.9 Hz, 1H), 4.08 (s,3H), 3.66 (dd, J=15.9, 9.8 Hz, 1H), 2.55 (s, 3H); LC-MS: method C, 2 to 98% B. RT =2.54 mm, MS (ESI) m/z: 584.25 (M+H). Analytical HPLC purity (method B): 100%.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2018/13776, 2018, A1 Location in patent: Page/Page column 421; 422

21
[ 62882-11-5 ]
[ 13395-36-3 ]
[ 135-02-4 ]
C₂₅H₂₄N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In 1,4-dioxane Reflux;

Reference： [1]Tobinaga, Hiroyuki; Kameyama, Takayuki; Asahi, Kentarou; Horiguchi, Tohru; Oohara, Miho; Taoda, Yoshiyuki; Hata, Kayoko; Hasegawa, Tsuyoshi; Tada, Yukio; Kurihara, Naoko; Kanda, Yasuhiko; Yagi, Shigenori; Tomari, Maki; Tanaka, Yoshikazu; Takahashi, Fumiyo; Taniguchi, Emiko; Takahara, Yukio; Shimada, Shinji; Takeyama, Chie; Yamamoto, Shoichi; Shinohara, Shunji; Kai, Hiroyuki [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 24]

22
[ 62882-11-5 ]
[ 13395-36-3 ]
[ 135-02-4 ]
C₂₅H₂₄N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid / 1,4-dioxane / Reflux 2: hydrazine hydrate; acetic acid / 95 °C

23
[ 62882-11-5 ]
[ 79-04-9 ]
C₁₁H₉ClN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(1,3-oxazol-2-yl)aniline; chloroacetyl chloride In acetic acid at 10 - 15℃; for 0.5h; Stage #2: With sodium acetate In water; acetic acid at 20℃; for 1.5h;

Reference： [1]Švajger, Urban; Bratkovič, Tomaž; Dolšak, Ana; Gobec, Stanislav; Mlinarič, Larisa; Ogorevc, Eva; Sova, Matej [Pharmaceuticals, 2021, vol. 14, # 3]

24
[ 62882-11-5 ]
C₂₂H₁₄FN₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: acetic acid / 0.5 h / 10 - 15 °C 1.2: 1.5 h / 20 °C 2.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydride / acetonitrile; N,N-dimethyl-d<SUB>6</SUB>-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere

Reference： [1]Švajger, Urban; Bratkovič, Tomaž; Dolšak, Ana; Gobec, Stanislav; Mlinarič, Larisa; Ogorevc, Eva; Sova, Matej [Pharmaceuticals, 2021, vol. 14, # 3]

25
[ 62882-11-5 ]
1-((2-chlorophenyl)sulfonyl)piperidine-4-carboxylic acid [ No CAS ]
1-((2-chlorophenyl)sulfonyl)-N-(4-(oxazol-2-yl)phenyl)piperidine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 80℃; for 0.333333h; Irradiation;	5.1.2 General procedure for the preparation of 6a to 6p General procedure: 2-chlorobenzenesulfonyl chloride (9.5mmol), methyl isonipecotate (14.25mmol) and N,N-diisopropylethylamine (28.5mmol) were dissolved in anhydrous dichloromethane (20mL) and were subjected to microwave irradiation at 80°C for 20min. After removal of the solvent under reduced pressure, the residue was re-dissolved in ethyl acetate (25mL), the organic layer was washed twice with 1N HCl (25mL), then aqueous solution of saturated sodium bicarbonate (25mL), brine (25mL), and was then dried over anhydrous sodium sulfate, filtered and concentrated. The crude product, a yellowish oil, was purified by flash chromatography (1:4 ethyl acetate/hexane solvent system) and the final product 4 was obtained as a yellow oil. Saponification of this methyl ester was achieved via the following procedure: a stirred solution of 4 (2.2g, 6.92mmol) in tetrahydrofuran (25mL) was treated with a 2M aqueous solution of lithium hydroxide (2mL) and the reaction was stirred overnight at room temperature. Following concentration in vacuo, water (15mL) and ethyl acetate were added (50mL). The mixture was then cooled to 0°C and 1N HCl was added dropwise, while stirring, until the reaction became acidic. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was recrystallized in diethyl ether, and 5 was obtained as a white solid (1.93g, 91% yield). Next, 0.23mmol of a carboxylic acid 5, 0.575mmol of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), 0.46mmol of corresponding aniline and a catalytic amount of 4-dimethylaminopyridine (DMAP) were dissolved in 20mL anhydrous dichloromethane and subjected to microwave irradiation at 80°C for 20min. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (20mL), washed twice with 1N HCl (2×25 mL) and aqueous solution of saturated sodium bicarbonate (25mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography using 1:1 ethyl acetate/hexane solvent system and final compounds were obtained.

Reference： [1]Wilt, Stephanie; Kodani, Sean; Valencia, Leah; Hudson, Paula K.; Sanchez, Stephanie; Quintana, Taylor; Morisseau, Christophe; Hammock, Bruce D.; Kandasamy, Ram; Pecic, Stevan [Bioorganic and Medicinal Chemistry, 2021, vol. 51]

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P321
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P337	If eye irritation persists:
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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.
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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.
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P401
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P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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. 62882-11-5 ] {[proInfo.proName]}

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[ 62882-11-5 ] Synthesis Path-Downstream 1~25

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Aryls

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Oxazoles

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