[ CAS No. 118994-90-4 ] {[proInfo.proName]}

Name: 118994-90-4|Oxazole-5-carboxylic acid|98%
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Quality Control of [ 118994-90-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 118994-90-4 ]

Product Details of [ 118994-90-4 ]

CAS No. :	118994-90-4	MDL No. :	MFCD04114931
Formula :	C₄H₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QCGMEWVZBGQOFN-UHFFFAOYSA-N
M.W :	113.07	Pubchem ID :	16340557
Synonyms :

Calculated chemistry of [ 118994-90-4 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	23.46
TPSA :	63.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.62
Log Po/w (XLOGP3) :	0.2
Log Po/w (WLOGP) :	0.37
Log Po/w (MLOGP) :	-1.21
Log Po/w (SILICOS-IT) :	0.31
Consensus Log Po/w :	0.06

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.06
Solubility :	9.77 mg/ml ; 0.0864 mol/l
Class :	Very soluble
Log S (Ali) :	-1.09
Solubility :	9.22 mg/ml ; 0.0815 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.55
Solubility :	31.6 mg/ml ; 0.279 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.79

Safety of [ 118994-90-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 118994-90-4 ]

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

Upstream synthesis route of [ 118994-90-4 ]
Downstream synthetic route of [ 118994-90-4 ]

[ 118994-90-4 ] Synthesis Path-Upstream 1~1

1
[ 118994-89-1 ]
[ 118994-90-4 ]

Yield	Reaction Conditions	Operation in experiment
87.5%	at 25℃; for 6.5 h; Large scale	An aqueous solution of lithium hydroxide monohydrate (124.5 kg of a solution preparedfrom 49.44 kg lithium hydroxide monohydrate dissolved in 319 kg water, 398 mol) was added to asolution of ethyl 5-oxazolecarboxylate (54 kg, 382.7 mol) in water (54 kg) maintaining the temperature below 25 °C. The reaction was stirred for 6.5 h and then conc. aqueous HCI (64.8 kg) was added maintaining the temperature below 25 °C, the crystallisation cooled to 5 °C and held forh. The product was filtered off, washed with cold water (88 kg), then isopropanol (171 kg) anddried under vacuum at 50 °C to give the title compound (37.88 kg, 87.Spercent).1H NMR (400 MHz, DMSO-d6) ppm 13.68 (br. 5., 1 H), 8.59 (5, 1 H), and 7.88 (5, 1 H).
87.5%	With lithium hydroxide monohydrate In water at 25℃; for 6.5 h; Large scale	An aqueous solution of lithium hydroxide monohydrate (124.5 kg of a solution prepared from 49.44 kg lithium hydroxide monohydrate dissolved in 319 kg water, 398 mol) was added to a solution of ethyl 5-oxazolecarboxylate (54 kg, 382.7 mol) in water (54 kg) maintaining the temperature below 25 °C. The reaction was stirred for 6.5 h and then cone, aqueous HCI (64.8 kg) was added maintaining the temperature below 25 °C, the crystallisation cooled to 5 °C and held for 1 h. The product was filtered off, washed with cold water (88 kg), then isopropanol (171 kg) and dried under vacuum at 50 °C to give the title compound (37.88 kg, 87.5percent). (0437) *H NMR (400 MHz, DMSO-cfe) δ ppm 13.68 (br. s., 1 H), 8.59 (s, 1 H), and 7.88 (s, 1 H).

Reference： [1] Patent: WO2016/193255, 2016, A1, . Location in patent: Page/Page column 21
[2] Patent: WO2018/29126, 2018, A1, . Location in patent: Page/Page column 49

[ 118994-90-4 ] Synthesis Path-Downstream 1~56

1
[ 118994-90-4 ]
methyl 5-(4-aminophenyl)-3-[[(trans-4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-2-thiophenecarboxylate [ No CAS ]
methyl 3-[[(trans-4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-5-{4-[(1,3-oxazol-5-ylcarbonyl)amino]phenyl}-2-thiophenecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 1 ,3-<strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (30 mg) in DMF (4 ml.) was added DIPEA (125 mg), followed by HATU (138 mg). The reaction was stirred at room temperature for 15 mins. Methyl 5-(4-aminophenyl)-3-[[(frans-4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-2- thiophenecarboxylate (100 mg, a synthesis of which is described as Intermediate 9) was added and the reaction mixture was stirred at 5O0C for 5 h. The reaction mixture was cooled and concentrated in vacuo. The residue was partitioned between DCM and sodium bicarbonate. The organic phase was collected and dried by passing through a hydrophobic frit and was concentrated in vacuo. The residue was loaded onto a 4Og silica ISCO cartridge. The cartridge was eluted with a gradient 5-100% EtOAc in cyclohexane to give the title compound. <n="99"/>MS calcd for (C27H3IN3O5S + H)+: 510 MS found (electrospray): (M+H)+ = 510

Reference： [1]Patent: WO2008/59042,2008,A1 .Location in patent: Page/Page column 97-98

2
[ 118994-90-4 ]
[ 1009627-18-2 ]
[ 1099774-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 17 - 25℃; for 2h;	Example 7: N-Methyl-iV-[4-[4-[(3S)-3-methylmorpholin-4-yll-6- (methylsulfbnylmethyl)pyrimidin-2-yll phenyll - 1.,2-oxazole-5-carboxamidelambda/-Methyl-4-[4-[(35)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2- yljaniline (191 mg, 0.53 mmol), l,2-<strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (90 mg, 0.79 mmol) and HATU (301 mg, 0.79 mmol) were dissolved in DMF (3 mL). Triethylamine (0.146 mL, 0.84 mmol) was added. The mixture was stirred at RT for 2 hours. Water (10 mL) was added to the stirred orange solution and the product was extracted into ethyl acetate (2 x 15 mL), dried over magnesium sulfate and evaporated to dryness. The crude product was purified by reverse phase chromatography to give the desired material as a white solid (41 mg).NMR Spectrum: 1U NMR (400.13 MHz, DMSOd6) delta 1.25 (3H, d), 3.20 (3H, s), 3.21 - 3.25 (IH, m), 3.42 (3H, s), 3.47 - 3.54 (IH, m), 3.63 - 3.67 (IH, m), 3.78 (IH, d), 3.97 - 4.01 (IH, m), 4.18 (IH, d), 4.52 (3H, s), 6.25 (IH, s), 6.88 (IH, s), 7.43 (2H, d), 8.33 - 8.35 (2H, m), 8.49 (IH, d) LCMS Spectrum: MH+ 472, Retention Time 1.76min, Method Monitor Acid

Reference： [1]Patent: WO2009/7749,2009,A2 .Location in patent: Page/Page column 128

3
[ 916570-23-5 ]
[ 118994-90-4 ]
1'-(1,3-oxazol-5-ylcarbonyl)-7,8-dihydro-6H-spiro[imidazo[1,5-a]pyridine-5,3'-pyrrolidine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 5 1'-(1,3-Oxazol-5-ylcarbonyl)-7,8-dihydro-6H-spiro[imidazo[1,5-a]pyridine-5,3'-pyrrolidine] 1.5 mmol of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> [118994-90-4] are dissolved in 5 ml of dichloro-methane and the solution is admixed at 0 C. with 1.6 mmol of chlorenamine. The reaction solution is subsequently stirred at room temperature for an hour and then added dropwise at 0 C. to a solution of 1 mmol of 7,8-dihydro-6H-spiro[imidazo[1,5-a]pyridine-5,3'-pyrrolidine] (Example 3a) and 2 mmol of triethylamine in 5 ml of dichloromethane. The reaction mixture is subsequently stirred at room temperature for 3 hours, poured into saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (3*). The combined organic extracts are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60 F) on the basis of the Rf value.
		1.5 mmol of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> [118994-90-4] are dissolved in 5 ml of dichloro- methane and the solution is admixed at 0C with 1.6 mmol of chlorenamine. The reaction solution is subsequently stirred at room temperature for an hour and then added dropwise at 00C to a solution of 1 mmol of Z.delta-dihydro-ThetaH-spirotimidazoti.S-aJpyridine-S.S'-pyrrolidine] (Example 3a) and 2 mmol of triethylamine in 5 ml of dichloromethane. The reaction mixture is subsequently stirred at room temperature for 3 hours, poured into saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (3x). The combined organic extracts are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Reference： [1]Patent: US2009/111840,2009,A1 .Location in patent: Page/Page column 9
[2]Patent: WO2006/128853,2006,A1 .Location in patent: Page/Page column 23

4
[ 118994-90-4 ]
[ 658700-12-0 ]
[ 1129250-00-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 773 - 777

5
[ 118994-90-4 ]
[ 518048-03-8 ]
[ 1064707-05-6 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5843 - 5855

6
[ 118994-90-4 ]
[ 869804-84-2 ]
[ 1148157-04-3 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3028 - 3038

7
[ 118994-90-4 ]
[ 1199814-68-0 ]
[ 1174651-12-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3204 - 3208

8
[ 118994-90-4 ]
[ 1207358-58-4 ]
[ 1207359-93-0 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;	Example 147;ca fv[0060] Synthesis of l-ethyl-3-(4-(4-morpholino-7-(oxazole-5-carbonyl)-5,6,7,8- tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (fv): (S)-l-ethyl-3-(4-(4-(3- methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (71 mg, 0.18 mmol) and N,N-diisopropylethylamine (6.0El uL, 0.34 mmol) were dissolved in N5N- Dimethylformamide (1.0 mL, 13 mmol). Oxazole-5-carboxylic acid (30.0 mg, 0.265 mmol) 1-hydroxybenzotriazole (27.8 mg, 0.206 mmol) and N-(3-dimethylaminopropyl)-N'- ethylcarbodiimide hydrochloride (49.9 mg, 0.260 mmol) were weighed out into a vial, and the solution of the amines was added, then the reaction stirred overnight. The resultant precipitate was removed by filtration and washed with H2O. The resulting solid was purified by reverse phase HPLC: 1H NMR (400 MHz, DMSO) delta 8.68 (s, IH), 8.63 (s, IH), 8.19 (d, J = 8.4 Hz, 2H), 7.88 (s, IH), 7.49 (d, J = 8.7 Hz, 2H), 6.18 (t, J = 5.5 Hz, IH), 4.98 - 4.54 (m, 2H), 4.19 - 4.07 (m, IH), 4.00 - 3.54 (m, 7H), 3.48 - 3.37 (m, IH), 3.15 - 3.08 (m, 2H), 2.92 - 2.65 (m, 2H), 1.26 (d, J = 6.6 Hz, 3H), 1.06 (t, J = 7.2 Hz, 3H)LC-MS: m/z = + 492.2 (M+H)+.

Reference： [1]Patent: WO2010/14939,2010,A1 .Location in patent: Page/Page column 175-176

9
[ 118994-90-4 ]
oxazole-5-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane;	Acylating reagent: Oxazole-5-carbonoyl chloride, generated from oxazole-5- carboxylic acid by standard treatment with 1.5 eq oxalyl chloride in DCM and catalytic amounts of DMF Compound 503 was obtained as a 70:30 mixture of starting material, impurities and compound 503 respectively. The mixture was used without further purification.
	With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 0℃; for 1.5h;Inert atmosphere;	General procedure: To the acid (1 eq) in 1 mL of THF and 1 drop of DMF at 0C, oxalyl chloride (1.2 eq) was added. The reaction was stirred under nitrogen for 1.5 hours and then the solution was concentrated. The acid chloride was continued to the next step.

Reference： [1]Patent: WO2010/22725,2010,A1 .Location in patent: Page/Page column 39-40
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 1127 - 1131

10
[ 118994-90-4 ]
[ 1257443-12-1 ]
[ 1257444-27-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In dichloromethane; N,N-dimethyl-formamide; for 2h;	Example 4-13: Synthesis of (R)-ethyl 4-(5'-fluoro-2'-methoxybipheny}-4-yI)«3-{oxazole~ 5«carboxamido)butanoate; To a solution of oxazole-5-carboxyiic acid (70 mg, 0.61 mmol) in DMF (1.5 mL) and DCM (1.5 mL) is added (R)-ethyl 3-amino«4~(5'-fluoro-2'-methoxybiphenyl-4-yi)butanoate hydrochloride, intermediate 10, (150 mg, 0.41 mmol), HATU (233 mg. 0.61 mmol), and TEA (284 muL, 2.04 mmol). After stirring for 2 hours, the reaction is quenched with H2O, and the crude is diluted with EtOAc, the organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue is purified by RP- HPLC (SupsilonnFire C18, H8O(0.1% TFA)ZCH3CN), and then lyophilized to give (R)-ethyl 4-(5'- ftuoro-2'-methoxybiphenyl-4-y[)-3-(oxazole-5-carboxamido)butanoate (157 mg). HPLC retention time = 1.50 minutes (condition A); MS (rn-M) = 427.4: 1 H NMR (400 MHz, CHLOROFORM-cO delta ppm 1.19 (t, J-7.2 Hz1 3 H) 2.46 - 2.62 (m, 2 H) 2.86 (dd, ,/=13.6, 8.1 Hz, 1 H) 3.02 (dd, J=13.6, 6.1 Hz, 1 H) 3.67 (s, 3 H) 4.05 - 4.15 (m, 2 H) 4.52 - 4.69 (m, 1 H) 6,76 - 6.82 (m, 1 H) 6.83 - 6.96 (m, 2 H) 7.1 1 - 7.21 (m, 3 H) 7.37 (d, J=8.1 Hz, 2 H) 7.61 (S1 1 H) 7.80 (s, 1 H)
157 mg	With triethylamine; HATU; In dichloromethane; N,N-dimethyl-formamide; for 2h;	To a solution of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (70 mg, 0.61 mmol) in DMF (1.5 mL) and DCM (1.5 mL) is added (R)-ethyl 3-amino-4-(5'-fluoro-2'-methoxybiphenyl-4-yl)butanoate hydrochloride, intermediate 8-3, (150 mg, 0.41 mmol), HATU (233 mg, 0.61 mmol), and TEA (284 muL, 2.04 mmol). After stirring for 2 hours, the reaction is quenched with H2O, and the crude is diluted with EtOAc, the organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue is purified by RP-HPLC (SunFire C18, H2O(0.1% TFA)/CH3CN), and then lyophilized to give (R)-ethyl 4-(5'-fluoro-2'-methoxybiphenyl-4-yl)-3-(oxazole-5-carboxamido)butanoate (157 mg). HPLC retention time = 1.50 minutes (condition A); MS (m+1) = 427.4; 1 H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19 (t, J=7.2 Hz, 3 H) 2.46 - 2.62 (m, 2 H) 2.86 (dd, J=13.6, 8.1 Hz, 1 H) 3.02 (dd, J=13.6, 6.1 Hz, 1 H) 3.67 (s, 3 H) 4.05 - 4.15 (m, 2 H) 4.52 - 4.69 (m, 1 H) 6.76 - 6.82 (m, 1 H) 6.83 - 6.96 (m, 2 H) 7.11 - 7.21 (m, 3 H) 7.37 (d, J=8.1 Hz, 2 H) 7.61 (s, 1 H) 7.80 (s, 1 H)

Reference： [1]Patent: WO2010/136493,2010,A1 .Location in patent: Page/Page column 115-116
[2]Patent: EP2640375,2016,B1 .Location in patent: Paragraph 0304-0305

11
[ 118994-90-4 ]
4-phenyldecahydroquinolin-4-ol [ No CAS ]
C₁₉H₂₂N₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2359 - 2364

12
[ 118994-90-4 ]
AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) [ No CAS ]
[(C₃H₂NO)Au(1,3-bis(2,6-diisopropyl)phenyl-imidazol-2-ylidene)] [ No CAS ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 5455 - 5457

13
[ 118994-90-4 ]
1-amino-cyclopropanecarboxylic acid 4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylamide-trifluoroacetic acid salt [ No CAS ]
[ 1126632-11-8 ]

Yield	Reaction Conditions	Operation in experiment
25%		125a) <strong>[118994-90-4]oxazole-5-carboxylic acid</strong>{1-[4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylcarbamoyl]-cyclopropyl}-amide57.5 muL (0.41 mmol) of TEA and 48 mg (0.15 mmol) of TBTU were added to a solution of 15.4 mg (0.14 mmol) of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> in 1.5 mL DMF and the mixture was stirred for 5 min at RT. Then 67.5 mg (0.14 mmol) of 1-amino-cyclopropanecarboxylic acid 4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylamide-trifluoroacetic acid salt (from 85a) were added and the mixture was stirred for 2 h at ambient temperature. The reaction mixture was purified by chromatography (reversed phase).Yield: 25% of theoryC23H20F3N3O5 (475.42)Mass spectrum: [M+H]+=476

Reference： [1]Patent: US2011/263626,2011,A1 .Location in patent: Page/Page column 59

14
[ 118994-90-4 ]
(R)-ethyl 3-amino-4-(5'-fluoro-2'-methoxybiphenyl-4-yl)butanoate hydrochloride [ No CAS ]
[ 96042-30-7 ]
(R)-ethyl 4-(5'-fluoro-2'-methoxybiphenyl-4-yl)-3-(oxazole-5-carboxamido)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethanolamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide;	Example 4-6 Synthesis of (R)-ethyl 4-(5'-fluoro-7-methoxybiphenyl-4-yl)-3-(oxazole-5-carboxamido)butanoate To a solution of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (70 mg, 0.61 mmol) in DMF (1.5 mL) and DCM (1.5 mL) is added (R)-ethyl 3-amino-4-(5'-fluoro-2'-methoxybiphenyl-4-yl)butanoate hydrochloride, intermediate 8-3, (150 mg, 0.41 mmol), HATU (233 mg, 0.61 mmol), and TEA (284 muL, 2.04 mmol). After stirring for 2 hours, the reaction is quenched with H2O, and the crude is diluted with EtOAc, the organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue is purified by RP-HPLC (SunFire C18, H2O (0.1% TFA)/CH3CN), and then lyophilized to give (R)-ethyl 4-(5'-fluoro-2'-methoxybiphenyl-4-yl)-3-(oxazole-5-carboxamido)butanoate (157 mg). HPLC retention time=1.50 minutes (condition A); MS (m+1)=427.4; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19 (t, J=7.2 Hz, 3H) 2.46-2.62 (m, 2H) 2.86 (dd, J=13.6, 8.1 Hz, 1H) 3.02 (dd, J=13.6, 6.1 Hz, 1H) 3.67 (s, 3H) 4.05-4.15 (m, 2H) 4.52-4.69 (m, 1H) 6.76-6.82 (m, 1H) 6.83-6.96 (m, 2H) 7.11-7.21 (m, 3H) 7.37 (d, J=8.1 Hz, 2H) 7.61 (s, 1H) 7.80 (s, 1H)

Reference： [1]Patent: US2012/122844,2012,A1

15
[ 141449-85-6 ]
[ 118994-90-4 ]
C₁₅H₂₁N₃O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9181 - 9194,14

16
[ 118994-90-4 ]
[ 1333425-31-2 ]
[ 1333426-28-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7189 - 7193

17
[ 500-22-1 ]
[ 118994-90-4 ]
[ 119072-55-8 ]
[ 769-92-6 ]
[ 1417699-73-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 534 - 546

18
[ 118994-90-4 ]
[ 1447911-00-3 ]
[ 1447911-94-5 ]

Yield	Reaction Conditions	Operation in experiment
40.7 mg	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h;	Example 69 4- ( (4-Fluorobenzyl) oxy) -1- (l-methyl-2- (1, 3-oxazol-5-yl) -1H- benzimidazol-6-yl) pyridin-2 (1H) -one A mixture of 1- ( 4-amino-3- (methylamino) phenyl) -4- ( ( 4- fluorobenzyl) oxy) pyridin-2 ( 1H) -one (100 mg) , oxazole-5- carboxylic acid (33.3 mg) , HATU (118 mg) , N,N- diisopropylethylamine (0.154 ml) and DMF (2 ml) was stirred at room temperature for 2 h. The mixture was poured into saturated NaHCC>3 solution and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgS04 and concentrated in vacuo. The resulting residue was dissolved in AcOH (2 ml) , and the mixture was stirred at 80C for 2 h. The mixture was concentrate in vacuo. The residue was purified by NH silica gel column chromatography (MeOH/EtOAc) . The resulting solid was washed with EtOAc/hexane to give the title compound (40.7 mg) as an off-white solid. MS (ESI+) : [M+H]+ 417.2. 1H NMR (300 MHz, DMSO-d6) : delta 4.03 (3H, s) , 5.15 (2H, s) , 6.01 (1, d, J = 2.6 Hz), 6.12 (1H, dd, J = 2.6, 7.6 Hz), 7.18-7.32 (3H, m) , 7.54 (2H, dd, J = 5.3, 8.7 Hz), 7.64 (1H, d, J = 7.6 Hz), 7.70-7.80 (2H, m) , 8.02 (1H, s) , 8.72 (1H, s) .

Reference： [1]Patent: WO2013/105676,2013,A1 .Location in patent: Page/Page column 157; 158

19
[ 52333-90-1 ]
[ 118994-90-4 ]
[ 1448806-52-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 45℃;Inert atmosphere;	General procedure: To a solution of the benzoxazole core (1.0 eq) in DCM (2 mL) was added the carboxylic acid (1.2 eq), EDCI (1.2 eq) and DMAP (0.1 eq). The solution was stirred under nitrogen at 45 C overnight. Work-up 1 (W1): The solution was extended with DCM, a saturated solution of sodium bicarbonate was added and the mixture was extracted three times with DCM. The combined organic layers were then washed with brine, dried with sodium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel, eluting ethyl acetate/cyclohexane 50:50 led to the desired carboxamide. Work-up 2 (W2): Water (approximately 2 mL) was added to the reaction mixture and it was transferred to the fridge overnight. The resulting precipitate was filtered and gave the desired carboxamide.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 450 - 465

20
[ 118994-90-4 ]
4-chloro-3-(oxazolo[4,5-b]pyridin-2-yl)benzenamine [ No CAS ]
[ 1448806-06-1 ]

Yield	Reaction Conditions	Operation in experiment
9%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 45℃;Inert atmosphere;	General procedure: To a solution of the benzoxazole core (1.0 eq) in DCM (2 mL) was added the carboxylic acid (1.2 eq), EDCI (1.2 eq) and DMAP (0.1 eq). The solution was stirred under nitrogen at 45 C overnight. Work-up 1 (W1): The solution was extended with DCM, a saturated solution of sodium bicarbonate was added and the mixture was extracted three times with DCM. The combined organic layers were then washed with brine, dried with sodium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel, eluting ethyl acetate/cyclohexane 50:50 led to the desired carboxamide.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 450 - 465

21
[ 118994-90-4 ]
[ 1448807-26-8 ]
[ 1448806-73-2 ]

Yield	Reaction Conditions	Operation in experiment
6%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 45℃;Inert atmosphere;	General procedure: To a solution of the benzoxazole core (1.0 eq) in DCM (2 mL) was added the carboxylic acid (1.2 eq), EDCI (1.2 eq) and DMAP (0.1 eq). The solution was stirred under nitrogen at 45 C overnight. Work-up 1 (W1): The solution was extended with DCM, a saturated solution of sodium bicarbonate was added and the mixture was extracted three times with DCM. The combined organic layers were then washed with brine, dried with sodium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel, eluting ethyl acetate/cyclohexane 50:50 led to the desired carboxamide.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 450 - 465

22
[ 118994-90-4 ]
[ 1448807-27-9 ]
[ 1448806-87-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 45℃;Inert atmosphere;	General procedure: To a solution of the benzoxazole core (1.0 eq) in DCM (2 mL) was added the carboxylic acid (1.2 eq), EDCI (1.2 eq) and DMAP (0.1 eq). The solution was stirred under nitrogen at 45 C overnight. Work-up 1 (W1): The solution was extended with DCM, a saturated solution of sodium bicarbonate was added and the mixture was extracted three times with DCM. The combined organic layers were then washed with brine, dried with sodium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel, eluting ethyl acetate/cyclohexane 50:50 led to the desired carboxamide. Work-up 2 (W2): Water (approximately 2 mL) was added to the reaction mixture and it was transferred to the fridge overnight. The resulting precipitate was filtered and gave the desired carboxamide.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 450 - 465
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 828 - 835

23
[ 118994-90-4 ]
(S)-9-ethyl-8-(2-methylpyrimidin-5-yl)-N-(pyrrolidin-3-yl)-9H-purin-6-amine dihydrochloride [ No CAS ]
[ 76-05-1 ]
(R)-(3-((9-ethyl-8-(2-methylpyrimidin-5-yl)-9H-purin-6-yl)amino)pyrrolidin-1-yl)(oxazol-5-yl)methanone trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate IIA -7 A solution of (lS,)-9-ethyl-8-(2-methylpyrimidin-5-yl)-N-(pyrrolidin-3-yl)-9H-purin-6-amine, 2HC1 (Intermediate II A) (25 mg, 0.06 mmol) in DMF (771 L) was added to a 2 dram vial containing Si-Carbodiimide (209 mg, 0.193 mmol), HOBT (17.70 mg, 0.1 16 mmol), DIEA (53.8 mu, 0.308 mmol) and <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (1 lmg, 0.095 mmol). The vial was sealed and its contents were allowed to stir overnight at room temperature. Si-Carbonate (209mg, 0.92 mmol) was added to the vial along with 1 mL of DMF (to scavenge any HOBt or unreacted carboxylic acid) and the vial was resealed and its contents were allowed to stir for 7 hours at room temperature. The reaction mixture was filtered through a 10 micron Whatman filter and washed with DMSO (1 mL). The filtered liquid was directly was purified by HPLC (0: 100 to 95 :5 acetonitrile:water: 0.1% v/v TFA modifier). The purified fraction was concentrated in vacuo to afford (R)-(3-((9-ethyl-8-(2-methylpyrimidin-5-yl)-9H-purin-6-yl)amino)pyrrolidin- 1 - yl)(oxazol-5-yl)methanone as a TFA salt. 1H NMR (600 MHz, DMSO- d6) delta 9.10 - 9.06 (m, 2H), 8.55 - 8.50 (m, 1H), 8.37 - 8.25 (m, 1H), 7.78 - 7.69 (m, 1H), 4.86 - 4.70 (m, 1H), 4.32 - 4.21 (m, 2H), 4.1 1 - 3.35 (m, 5H), 2.73 - 2.67 (m, 3H), 2.36 - 2.02 (m, 2H), 1.32 - 1.23 (m, 3H). Calc'd for C20H22N9O2 [M+H]+, 420; found 420.

Reference： [1]Patent: WO2014/75393,2014,A1 .Location in patent: Page/Page column 76

24
[ 118994-90-4 ]
[ 1620690-92-7 ]
[ 1620688-37-0 ]

Yield	Reaction Conditions	Operation in experiment
		2-Acetamido-N-((1S)-1-(4-((3R)-1-(5-((2,2-difluorocyclopropyl)methoxy)pyrid rrolidin-3-yloxy)phenyl)ethyl)-4-methylthiazole-5-carboxamide 25.7 mg (0.13 mmol) 2-acetylamino-4-methyl-thiazole-5-carboxylic acid, 43.9 muIota (0.26 mmol) DIPEA and 45.3 mg (0.14 mmol) TBTU are added to 3 ml_ DMF and stirred for 10 min. Then 50.0 mg (0.13 mmol) of the amine XXII.1 are added and the resulting mixture is stirred at r.t. over night. Afterwards the mixture is directly purified by HPLC (MeOH/H2O/TFA). C28H31F2N5O4S (M= 57 .6 g/mol) ESI-MS: 572 [M+H]+ Rt (HPLC):1.11 min (method C) The following compounds are prepared analogously to example 2.1 : For the examples CIP is used as coupling reagent ACN is used as solvent.For the examples 2.3 - 2.8, 2.122 and 2.125 the reaction time is 2 h. For the examples 2.69 - 2.93 and 2.99-2.121 TEA is used as base. For example 2.55 the product is added to TFA/H20 (95/5) and stirred at r.t. 3 h to cleave the ferf-butyl group. For example 2.64 the product is added to methanol and treated with aq. HCI solution (c = 1 mol/L) to cleave the THP protecting group. For the examples where 1-chloro-N,N-2-trimethylpropenylamine is used, the reagent is added to the a mixture of the appropiate acid in DCM and stirred at r.t. for 30 min. Then the appropriate amine and DIPEA are added and the resulting mixture is stirred at r.t. for 1 h. After aq. work up the crude product is purified by HPLC.

Reference： [1]Patent: WO2014/114578,2014,A1 .Location in patent: Page/Page column 137; 138; 150

25
[ 118994-90-4 ]
[ 10269-01-9 ]
N-(3-bromobenzyl)oxazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 15 - 25℃;Inert atmosphere;	To a solution of (3-bromophenyl)methanamine (820 mg, 4.4 mmol) and oxazole- 5-carboxylic acid (500 mg, 4.4 mmol) in DCM (50 mL), was added HOBt (1.2 g, 8.8 mmol), TEA (2.2 g, 22 mmol) and EDCI (1.7 g, 8.8 mmol). The resulting mixture was stirred at r.t. overnight, then partitioned between water and DCM. The organic phase was dried over NaS04, filtered and concentrated in vacuo to afford a residue that was purified by column chromatography on silica gel (1 : 1 pet ether/ EtOAc) to afford the title compound. 1H NMR (400 MHz, CDCls): 57.83 (s, 1H), 7.70 (s, 1H), 7.41 (d, / = 1.6 Hz, 1H), 7.37 (dt, / = 7.6 Hz, 1.6 Hz, 1H), 7.21-7.14 (m, 1H), 7.16 (t, / = 7.6 Hz, 1H), 6.57 (br, 1H), 4.53 (d, / = 6.0 Hz, 2H).
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	To a solution of (3-bromophenyl)methanamine (820 mg, 4.4 mmol) and oxazole-5- carboxylic acid (500 mg, 4.4 mmol) in DCM (50 mL), was added HOBt (1.2 g, 8.8 mmol), TEA (2.2 g, 22 mmol) and EDCI (1.7 g, 8.8 mmol). The resulting mixture was stirred at r.t. overnight, then partitioned between water and DCM. The organic phase was dried over Na504, filtered and concentrated in vacuo to afford a residue that was purified by column chromatography on silicagel (1:1 pet ether EtOAc) to afford compound, 1-15. ?H NMR (400 MHz, CDC13): oe 7.83 (s,1H), 7.70 (s, 1H), 7.41 (d, J= 1.6 Hz, 1H), 7.37 (dt, J= 7.6 Hz, J= 1.6 Hz, 1H), 7.21-7.14 (m,1H), 7.16 (t, J= 7.6 Hz, 1H), 6.57 (br, 1H), 4.53 (d, J 6.0 Hz, 2H).

Reference： [1]Patent: WO2014/146490,2014,A1 .Location in patent: Page/Page column 74
[2]Patent: WO2014/146246,2014,A1 .Location in patent: Page/Page column 62

26
[ 118994-90-4 ]
[ 19348-53-9 ]
C₁₈H₁₀ClN₃O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 7959 - 7971

27
[ 118994-90-4 ]
[ 108-98-5 ]
5-(phenylthio)oxazole [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 8733 - 8736

28
[ 118994-90-4 ]
C₂₀H₂₃ClFNO₂*ClH [ No CAS ]
[ 1257266-56-0 ]

Yield	Reaction Conditions	Operation in experiment
103 mg		DIPEA (228 mu, 1.3 mmol) was added to a solution of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (49.4 mg, 437 muetaiotaomicron), Compound 11 (HCl; 175 mg, 437 mupiiotaomicron) and HATU (249 mg, 656 muetaiotaomicron) in DMF (2 mL). The resulting mixture was stirred for 10 minutes at room temperature, at which point LC/MS showed completion. 5.0 M aqueous LiOH (699 mu., 3.5 mmol) was added and the mixture was stirred at room temperature for 1 hour. Concentrated HCl (-0.5 mL) was added until the reaction mixture became acidic and the crude mixture was purified by preparative HPLC (20-80% MeCN in water with 0.05% TFA) to yield Comparison Compound C4 (103 mg) as a white solid. MS m/z [M+H]+ calc'd for C22H20CIFN2O4, 431.11 ; found 431.1. Comparison Compound C4 is described in example 68-1 of. U.S. Patent No. 8,263,629 to Coppola et al.

Reference： [1]Patent: WO2016/133803,2016,A1 .Location in patent: Page/Page column 57; 58

29
[ 118994-90-4 ]
[ 2993-24-0 ]
4-(oxazol-5-yl)carbonylamino(pentafluorosulfanyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		Example 79 Synthesis of Compound 82 Z?NH, p=0, n=1, q=1, m=0; Synthesis of 4-(oxazol-5-yl)carbonylaminopentafluorosulfanylbenzene Into a 100 ml flask equipped with a stirrer, 1.0 g (8.84 mmol) of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong>, 10 ml of ethyl acetate, and subsequently 1.58 g (9.72 mmol) of carbonyl diimidazole (CDI) were added, and refluxed for 2.5 hours. Subsequently, 1.84 g (8.40 mmol) of 4-aminopentafluorosulfanylbenzene was added and refluxed again for 9 hours. After completion of the reaction, 2 g of diatomaceous earth was added, and the reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a reversed-phase type column chromatography (eluent; acetonitrile/0.1% aqueous formic acid solution=0/100 to 95/5 (solvent ratio)), to obtain 4-(oxazol-5-yl)carbonylaminopentafluorosulfanylbenzene 1.37 g (yield 52%) as white powder. Herein, 4-(oxazol-5-yl)carbonylaminopentafluorosulfanylbenzene is a novel compound having the following property values. 1H-NMR (DMSO-d6, delta (ppm)); 7.89-8.00 (4H, m), 8.06 (1H, s), 8.71 (1H, s), 10.84 (1H, bs) MS (ES+); 356(M+1+CH3CN), 315(M+1)

Reference： [1]Patent: US2016/244407,2016,A1 .Location in patent: Paragraph 0694-0699

30
[ 118994-90-4 ]
2-(2-phenyl)thiazol-4-ylethylamine dihydrochloride [ No CAS ]
N-(2-(2-phenylthiazol-4-yl)ethyl)oxazole-5-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9686 - 9720

31
[ 1126-09-6 ]
[ 118994-90-4 ]
ethyl 1-(oxazole-5-carbonyl)piperidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.6 g	With O-(7-azabenzotriazol-lyl)-N,N,N?,N?-tetramethylyronium hexafluorophosphate; triethylamine; In 2-methyltetrahydrofuran; at 20℃; for 18h;	To a solution of ethyl piperidine-4-carboxylate (15.3 g, 97 mmol) on 2-MeTHF (300 mL) at rt, <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (11.00 g, 97 mmol), HATU (38.9 g, 102 mmol) and Et3N (14.92 mL, 107 mmol) were added. The reaction mixture was stirred at rt for 18 hours. Water (500 mL) was added and extracted with EtOAc (2 x 300 mL). The combined organic phases were dried over Na2504, filtered off and evapporated to dryness. The residue was purified bychromatography [silica, CyHI(EtOAc-EtOH 3:1) 100/0 to 75/25] to afford the title compound (23.6 g, purity: >95% by LCMS, recovery: 96%) as a yellow oil. LCMS (m/z) 253 (M+H), retention time: 1.68 mm, method 1 20V.

Reference： [1]Patent: WO2016/185423,2016,A1 .Location in patent: Page/Page column 78

32
[ 118994-89-1 ]
[ 118994-90-4 ]

Yield	Reaction Conditions	Operation in experiment
87.5%	With lithium hydroxide monohydrate; water; at 25℃; for 6.5h;Large scale;	An aqueous solution of lithium hydroxide monohydrate (124.5 kg of a solution preparedfrom 49.44 kg lithium hydroxide monohydrate dissolved in 319 kg water, 398 mol) was added to asolution of <strong>[118994-89-1]ethyl 5-oxazolecarboxylate</strong> (54 kg, 382.7 mol) in water (54 kg) maintaining the temperature below 25 C. The reaction was stirred for 6.5 h and then conc. aqueous HCI (64.8 kg) was added maintaining the temperature below 25 C, the crystallisation cooled to 5 C and held forh. The product was filtered off, washed with cold water (88 kg), then isopropanol (171 kg) anddried under vacuum at 50 C to give the title compound (37.88 kg, 87.S%).1H NMR (400 MHz, DMSO-d6) ppm 13.68 (br. 5., 1 H), 8.59 (5, 1 H), and 7.88 (5, 1 H).
87.5%	With lithium hydroxide monohydrate; In water; at 25℃; for 6.5h;Large scale;	An aqueous solution of lithium hydroxide monohydrate (124.5 kg of a solution prepared from 49.44 kg lithium hydroxide monohydrate dissolved in 319 kg water, 398 mol) was added to a solution of <strong>[118994-89-1]ethyl 5-oxazolecarboxylate</strong> (54 kg, 382.7 mol) in water (54 kg) maintaining the temperature below 25 C. The reaction was stirred for 6.5 h and then cone, aqueous HCI (64.8 kg) was added maintaining the temperature below 25 C, the crystallisation cooled to 5 C and held for 1 h. The product was filtered off, washed with cold water (88 kg), then isopropanol (171 kg) and dried under vacuum at 50 C to give the title compound (37.88 kg, 87.5%). (0437) *H NMR (400 MHz, DMSO-cfe) delta ppm 13.68 (br. s., 1 H), 8.59 (s, 1 H), and 7.88 (s, 1 H).

Reference： [1]Patent: WO2016/193255,2016,A1 .Location in patent: Page/Page column 21
[2]Patent: WO2018/29126,2018,A1 .Location in patent: Page/Page column 49

33
[ 4318-42-7 ]
[ 118994-90-4 ]
(4-isopropylpiperazin-1-yl)(oxazol-5-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		Oxalyl chloride (47.7 kg, 375.8 mol) was added to a solution of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (32.88 kg, 290.8 mol) in isopropyl acetate (144 kg) maintaining the temperature at 52-58 C. The temperature was increased to 58.5 C, stirred for 5 h and then cooled to 20 C. The reactionmixture was added to a solution of 1-(isopropyl)piperazine (41 kg, 319.8 mol) and potassium carbonate (118.4kg) in isopropyl acetate (348 kg) and water (103 kg) maintaining the temperature below 25 C. The reaction was stirred for 15 mins, the temperature was increased to 33 C and the organic phase washed with water (191 kg), concentrated under reduced pressure to 95 L and cooled to 20 C. n-Heptane (157 kg) was added and the crystallisation stirred for 2 h, and theproduct filtered off, washed with n-heptane (157 kg) and dried under vacuum 40 C to give the title compound (57.14 kg, 88.0%).1H NMR (400 MHz, CDCI3-d) ppm 7.94 (5, 1 H), 7.56 (5, 1 H), 3.91-3.73 (m, 4 H), 2.75 (spt., J=6.5 Hz, 1 H), 2.63-2.52 (m, 4 H) and 1.06 (d, J=6.6 Hz, 6 H).
88%		Oxalyl chloride (47.7 kg, 375.8 mol) was added to a solution of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (32.88 kg, 290.8 mol) in isopropyl acetate (144 kg) maintaining the temperature at 52-58 C. The temperature was increased to 58.5 C, stirred for 5 h and then cooled to 20 C. The reaction mixture was added to a solution of l-(isopropyl)piperazine (41 kg, 319.8 mol) and potassium carbonate (118.4kg) in isopropyl acetate (348 kg) and water (103 kg) maintaining the temperature below 25 C. The reaction was stirred for 15 mins, the temperature was increased to 33 C and the organic phase washed with water (191 kg), concentrated under reduced pressure to 95 L and cooled to 20 C. n- Heptane (157 kg) was added and the crystallisation stirred for 2 h, and the product filtered off, washed with n-heptane (157 kg) and dried under vacuum 40 C to give the title compound (57.14 kg, 88.0%). (0441) *H NMR (400 MHz, CDC -d) delta ppm 7.94 (s, 1 H), 7.56 (s, 1 H), 3.91-3.73 (m, 4 H), 2.75 (spt., J=6.5 Hz, 1 H), 2.63-2.52 (m, 4 H) and 1.06 (d, J=6.6 Hz, 6 H).
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃;	A mixture of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (80 mg, 0.708 mmol), DIPEEA (0.124 mL, 0.708 mmol), and 1- isopropylpiperazine (0.111 mL, 0.778 mmol) in THF (5 mL) was treated with a 50% by weight solution of 2,4,6-tripropyl-l,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (0.463 mL, 0.778 mmol) and stirred at room temperature overnight. The reaction mixture was diluted with a small amount of MeOH and poured directly onto an SCX-SPE cartridge (5 g) that had been preconditioned with MeOH. The cartridge was washed with MeOH and the product eluted using a 2 M solution of ammonia in MeOH to give the title compound (126 mg, 72%). LCMS (Method C): Rt = 0.59 min, MH+ 224. The crude compound was taken forward into the next reaction step without further purification.

Reference： [1]Patent: WO2016/193255,2016,A1 .Location in patent: Page/Page column 21
[2]Patent: WO2018/29126,2018,A1 .Location in patent: Page/Page column 49
[3]Patent: WO2018/192864,2018,A1 .Location in patent: Page/Page column 122

34
[ 118994-90-4 ]
2-(2-aminopyridin-4-yl)-3-(phenylamino)-1,7-dihydropyrano[3,4-b]pyrrol-4(5H)-one [ No CAS ]
N-{4-[4-oxo-3-(phenylamino)-1,4,5,7-tetrahydropyrano[3,4-b]pyrrol-2-yl]pyridin-2-yl}-1,3-oxazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl acetamide; at 20℃; for 18h;	A solution of 1 ,3-<strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (21 mg, 0.19 mmol) and HATU (71 mg, 0, 19 mmol) in DMA (1 mL) was added to a mixture of 2-(2-Aminopyridin-4-yl)-3-(phenylamino)- 1 ,7-dihydropyrano[3,4-b]pyrrol-4(5H)-one (22; 50 mg, 0.16 mmol) and DIPEA (236 muIota_. 1.36 mmol) in DMA (1 mL) and stirred for 18 h at T. The mixture was concentrated and purified by Biotage (SNAP NH 25g, EtOAc:Hexane; MeOH:DCM) to give the title compound (2 mg, 3%). 1H-NMR (400 MHz, DMSO-d6), delta [ppm]= 4.05 (2H), 4.90 (2H), 6.60 (3H), 7.04 (2H), 7.36 (1 H), 7.50 (1 H), 8.22 (1 H), 8.25 (1 H), 8.35 (1 H), 8.66 (1 H), 10.95 (1 H), 12.22 (1 H)

Reference： [1]Patent: WO2017/102649,2017,A1 .Location in patent: Page/Page column 146

35
[ 118994-90-4 ]
N-{4-[4-oxo-3-(phenylamino)-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-2-yl]pyridin-2-yl}acetamide [ No CAS ]
N-{4-[3-anilino-6-(1,3-oxazol-5-ylcarbonyl)-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-2-yl]pyridin-2-yl}acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl acetamide; at 20℃; for 3h;	A solution of 1 ,3-<strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (31 mg. 0.28 mmol) and HATU (105 mg, 0.28 mmol) in DMA (1 ml.) was added to a mixture of N-{4-[4-oxo-3-(phenylamino)-4, 5,6,7- tetra ydro-1 H-pyrrolo[2,3-c]pyridin-2-yl]pyridin-2-yl}acetamide (24; 50 mg, 0.14 mmol) and DIPEA (48 muIota_, 0.28 mmol) in DMA (1 mL) and stirred for 3 h at RT. The mixture was concentrated and purified by preparative TLC (silica, MeOH:DCM) and digested with diethyl ether to give the title compound (17 mg, 27%). 1H-NMR (400 MHz, DMSO-d6), delta [ppm]= 2.09 (3H), 4.36 (2H), 5.1 1 (2H), 6.57 (2H), 6.60 (1 H), 7.02 (2H), 7.23 (1 H), 7.45 (1 H), 7.84 (1 H), 8.14 (1 H), 8.28 (1 H), 8.65 (1 H), 10.42 (1 H), 12.26 (1 H)

Reference： [1]Patent: WO2017/102649,2017,A1 .Location in patent: Page/Page column 206; 207

36
[ 118994-90-4 ]
5-amino-2-(3,4-difluorophenyl)benzothiazole [ No CAS ]
N-(2-(3,4-difluorophenyl)benzo[d]thiazol-5-yl)oxazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		A solution of 74g (151 mg, 0.577 mmol), <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (81.3 mg, 0.719 mmol), and DIEA (350 muL, 2.01 mmol) in DMF (3 mL) under Ar was stirred for 15 min before the addition of HATU (0.276 mg, 0.7245 mmol). The reaction mixture was stirred for 3 hour before being diluted with water. The precipitate was filtered off, dried, and recrystallized from EtOH to give a solid (156 mg, 76%): mp 245-047 C; ?H NMR (400 MHz, DMSO-d6) 6 10.70 (s, 1H), 8.70 (s, 1H), 8.56 (d, J 2.0 Hz, 1H), 8.17 (ddd, J= 11.3, 7.7, 2.2 Hz, 1H),8.14 (d, J? 8.7 Hz, 1H), 8.04 (s, 1H), 7.96 (dt, J 7.8, 2.9 Hz, 1H), 7.80 (dd, J= 8.7, 2.1 Hz, 1H), 7.66 (dt, J 10.4, 8.4 Hz, 1H); ElMS m/z 358.0 (M + 1) HPLC 100 area % (290 nm). Anal. Calcd for C,7H9F2N30S?0.1H20: C, 56.85; H, 2.58; N, 11.70. Found: C, 56.61; H, 274;N, 11.55.

Reference： [1]Patent: WO2017/127627,2017,A1 .Location in patent: Paragraph 0220

37
[ 118994-90-4 ]
20'-aminovinblastine [ No CAS ]
C₅₀H₆₀N₆O₁₀ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7591 - 7604

38
[ 118994-90-4 ]
[ 57260-71-6 ]
tert-butyl 4-(oxazole-5-carbonyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 932 - 939

39
6-(2'-Aminothiazol-4'-yl)-3,4-dihydrocarbostyril [ No CAS ]
[ 118994-90-4 ]
N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; propylphosphonic anhydride; In ethyl acetate; acetonitrile; at 48.5℃; for 96h;Sealed tube;	To a suspension of 6-(2-aminothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.100 g, 0.408 mmol) and <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (0.051 g, 0.448 mmol), and pyridine (0.15 mL, 1.832 mmol) in acetonitrile (4 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.85 mL, 1.431 mmol). The sealed tube was heated to 48.5 C. for 4 days and the precipitation formed. After cooling, the solid was collected by filtration and washed with cold dichloromethane to give N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide (0.121 g, 87%) as a beige solid. 1H NMR (400 MHz, DMSO-d): delta 13.03 (bs, 1H), 10.18 (s, 1H), 8.72 (s, 1H), 8.29 (s, 1H), 7.75 (s, 1H), 7.71 (dd, 1H, J=8.4, 1.6 Hz), 7.56 (s, 1H), 6.90 (d, 1H, J=8.4 Hz), 2.93 (m, 2H), 2.48 (partial masked under d-DMSO, m, 2H). MS (ESI): Calcd. for C16H12N4O3S: 340, found 341 (M+1)+.

Reference： [1]Patent: US2018/86752,2018,A1 .Location in patent: Paragraph 0143; 0144

40
[ 118994-90-4 ]
6-chloro-N₄-(4-methoxybenzyl)pyridine-3,4-diamine [ No CAS ]
C₁₇H₁₅ClN₄O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4213 - 4227

41
[ 118994-90-4 ]
tert-butyl N-[1-[2-(aminomethyl)-8-[tert-butoxycarbonyl(methyl)amino]-6-fluoro-9H-pyrimido[4,5-b]indol-4-yl]pyrrolidin-3-yl]-N-methylcarbamate [ No CAS ]
tert-butyl N-[1-[8-[tert-butoxycarbonyl(methyl)amino]-6-fluoro-2-[(oxazole-5-carbonylamino)methyl]-9H-pyrimido[4,5-b]indol-4-yl]pyrrolidin-3-yl]-N-methylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice;	General procedure: Following the general procedure below, the data are reported as a) mass of starting material; b) mass of acid; c) mass of EDCI; d) volume of DCM; e) volume of NEt3; f) mass of product obtained.To an ice cold solution of corresponding primary amine 6a-d (0.05 - 0.38 mmol, 1 eq), corresponding acid (0.06 - 0.48 mmol, 1.3 eq) and EDCI (0.05 - 0.49 mmol, 1.3 eq) in DCM was added NEt3 (0.06 - 0.53 mmol, 1.4 eq) and the mixture was warmed to RT and stirred for 16 h. The reaction mixture was loaded directly onto a pre-equilibrated silica column and purified by silica gel column chromatography (gradient = 0-100% EtOAc in petroleum ether (bp. 40-60)). The appropriate fractions were combined and concentrated in vacuo to give the corresponding Boc-protected final compound 7.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2998 - 3003

42
[ 118994-90-4 ]
tert-butyl N-[2-(aminomethyl)-4-[3-(dimethylamino)pyrrolidin-1-yl]-6-fluoro-9H-pyrimido[4,5-b]indol-8-yl]-N-methylcarbamate [ No CAS ]
tert-butyl (4-(3-(dimethylamino)pyrrolidin-1-yl)-6-fluoro-2-((oxazole-5-carboxamido)methyl)-9H-pyrimido[4,5-b]indol-8-yl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice;	General procedure: Following the general procedure below, the data are reported as a) mass of starting material; b) mass of acid; c) mass of EDCI; d) volume of DCM; e) volume of NEt3; f) mass of product obtained.To an ice cold solution of corresponding primary amine 6a-d (0.05 - 0.38 mmol, 1 eq), corresponding acid (0.06 - 0.48 mmol, 1.3 eq) and EDCI (0.05 - 0.49 mmol, 1.3 eq) in DCM was added NEt3 (0.06 - 0.53 mmol, 1.4 eq) and the mixture was warmed to RT and stirred for 16 h. The reaction mixture was loaded directly onto a pre-equilibrated silica column and purified by silica gel column chromatography (gradient = 0-100% EtOAc in petroleum ether (bp. 40-60)). The appropriate fractions were combined and concentrated in vacuo to give the corresponding Boc-protected final compound 7.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2998 - 3003

43
[ 118994-90-4 ]
tert-butyl N-[2-(aminomethyl)-4-[3-[(tert-butoxycarbonylamino)methyl]pyrrolidin-1-yl]-6-fluoro-9H-pyrimido[4,5-b]indol-8-yl]-N-methylcarbamate [ No CAS ]
tert-butyl N-[4-[3-[(tert-butoxycarbonylamino)methyl]pyrrolidin-1-yl]-6-fluoro-2-[(oxazole-5-carbonylamino)methyl]-9H-pyrimido[4,5-b]indol-8-yl]-N-methylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice;	General procedure: Following the general procedure below, the data are reported as a) mass of starting material; b) mass of acid; c) mass of EDCI; d) volume of DCM; e) volume of NEt3; f) mass of product obtained.To an ice cold solution of corresponding primary amine 6a-d (0.05 - 0.38 mmol, 1 eq), corresponding acid (0.06 - 0.48 mmol, 1.3 eq) and EDCI (0.05 - 0.49 mmol, 1.3 eq) in DCM was added NEt3 (0.06 - 0.53 mmol, 1.4 eq) and the mixture was warmed to RT and stirred for 16 h. The reaction mixture was loaded directly onto a pre-equilibrated silica column and purified by silica gel column chromatography (gradient = 0-100% EtOAc in petroleum ether (bp. 40-60)). The appropriate fractions were combined and concentrated in vacuo to give the corresponding Boc-protected final compound 7.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2998 - 3003

44
[ 118994-90-4 ]
C₂₆H₃₆FN₇O₄ [ No CAS ]
tert-butyl N-[4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-6-fluoro-2-[(oxazole-5-carbonylamino)methyl]-9H-pyrimido[4,5-b]indol-8-yl]-N-methylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice;	General procedure: Following the general procedure below, the data are reported as a) mass of starting material; b) mass of acid; c) mass of EDCI; d) volume of DCM; e) volume of NEt3; f) mass of product obtained.To an ice cold solution of corresponding primary amine 6a-d (0.05 - 0.38 mmol, 1 eq), corresponding acid (0.06 - 0.48 mmol, 1.3 eq) and EDCI (0.05 - 0.49 mmol, 1.3 eq) in DCM was added NEt3 (0.06 - 0.53 mmol, 1.4 eq) and the mixture was warmed to RT and stirred for 16 h. The reaction mixture was loaded directly onto a pre-equilibrated silica column and purified by silica gel column chromatography (gradient = 0-100% EtOAc in petroleum ether (bp. 40-60)). The appropriate fractions were combined and concentrated in vacuo to give the corresponding Boc-protected final compound 7.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2998 - 3003

45
[ 118994-90-4 ]
C₁₃H₁₈F₃N₅ [ No CAS ]
C₁₇H₁₉F₃N₆O₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 5596 - 5604

46
[ 118994-90-4 ]
C₁₄H₂₂N₄S [ No CAS ]
C₁₈H₂₃N₅O₂S [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 5596 - 5604

47
[ 118994-90-4 ]
C₂₄H₂₇FN₆O₃ [ No CAS ]
C₂₃H₂₀FN₇O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%		Compound E-Y3 (46 mg, 0.1 mmol) was dissolved in 3 mL dichloromethane (DCM)And 1 mL of trifluoroacetic acid (TFA), stirred at room temperature for 30 min,After the solvent was concentrated to dryness, 1 mL of DMF and 0.1 mL of diisopropylethylamine (DIEPA) were added.Stir and dissolve, add HATU (76 mg, 0.2 mmol) at room temperature.Oxazole-5-carboxylic acid(18 mg, 0.16 mmol), reaction for 6 h, TLC showed reaction 675F(DCM: MeOH = 10:1, Rf = 0.5), and the reaction mixture was poured into water.Extracted with a large amount of ethyl acetate, dried and concentrated, and separated by column chromatography(DCM: MeOH = 30:1) gave the title compound E-Y41,White solid(10 mg, 22% yield in two steps).

Reference： [1]Patent: CN109575013,2019,A .Location in patent: Paragraph 0407-0410

48
[ 118994-90-4 ]
5-(6-[[6-methoxy-5-(4-methylpiperazin-1-yl)pyridin-2-yl]amino]pyrimidin-4-yl)-2-(piperidin-4-yloxy)benzonitrile [ No CAS ]
5-(6-[[6-methoxy-5-(4-methylpiperazin-1-yl)pyridin-2-yl]amino]pyrimidin-4-yl)-2-([1-[(1,3-oxazol-5-yl)carbonyl]piperidin-4-yl]oxy)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 12h;	The title compound was prepared from 5-(6-[[6-methoxy-5-(4-methylpiperazin- l-yl)pyridin-2- yl]amino]pyrimidin-4-yl)-2-(piperidin-4-yloxy)benzonitrile and l,3-<strong>[118994-90-4]oxazole-5-carboxylic acid</strong> using Method A. The final product was purified by prep-HPLC under the following conditions: column, XBridge Prep C 18 OBD Column, 150 x 19 mm, 5 um; mobile phase, acetonitrile in water (with 10 mmol/L NH4HCO3 and 0.1 % NH3.H2O), 25 % to 40 % gradient in 7 min; detector, UV 254 nm. 5-(6-[[6-methoxy-5-(4-methylpiperazin- l-yl)pyridin-2- yl]amino]pyrimidin-4-yl)-2-([l-[(l,3-oxazol-5-yl)carbonyl]piperidin-4-yl]oxy)benzonitrile was obtained as yellow solid (29 mg, 17 %). HPLC: 98.5 % purity, RT = 2.44 min. MS: m/z = 596.2 [M+H]+. lH NMR (300 MHz, Methanol-^) delta 8.70-8.63 (m, 1 H), 8.35 (s, 1 H), 8.33-8.23 (m, 2 H), 8.07 (s, 1 H), 7.69 (s, 1 H), 7.48-7.38 (m, 1 H), 7.36-7.27 (m, 1 H), 7.27-7.17 (m, 1 H), 5.08- 4.99 (m, 1 H), 4.06 (s, 3 H), 3.96-3.89 (m, 4 H), 3.11-3.04 (m, 4 H), 2.68-2.62 (m, 4 H), 2.36 (s, 3 H), 2.17-2.10 (m, 2 H), 2.08- 1.93 (m, 2 H).

Reference： [1]Patent: WO2019/79375,2019,A1 .Location in patent: Page/Page column 60; 61; 108

49
[ 118994-90-4 ]
6-([4-[3-cyano-4-(piperidin-4-yloxy)phenyl]pyrimidin-2-yl]amino)-2-methoxy-N,N-dimethylpyridine-3-carboxamide [ No CAS ]
6-([4-[3-cyano-4-([1-[(1,3-oxazol-5-yl)carbonyl]piperidin-4-yl]oxy)phenyl]pyrimidin-2-yl]amino)-2-methoxy-N,N-dimethylpyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 18h;	General procedure: To a solution of 6- chloro-2-methoxypyridine-3-carboxylic acid (190 mg, 1.01 mmol) in N,N-dimethylformamide (2 mL) was added HATU (722 mg, 1.90 mmol), dimethylamine hydrochloride (165 mg, 2.03 mmol) and DIEA (614 mg, 4.75 mmol) at room temperature. The resulting mixture was stirred for 6 h at 35 C. When the reaction was done, the reaction mixture was diluted with H20 (20 mL) and extracted with ethyl acetate (50 mL x 3). The organic phases were combined, washed with brine and dried over Na2S04. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with MeOH in EtOAc (0 % to 10 % gradient) to yield 6-chloro-2-methoxy-N,N-dimethylpyridine-3-carboxamide as an yellow oil (129 mg, 59 %). MS: m/z = 214.9 [M+H]+.

Reference： [1]Patent: WO2019/79373,2019,A1 .Location in patent: Paragraph 00180; 00297

50
[ 118994-90-4 ]
(5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)(piperidin-4-yl)methanone hydrochloride [ No CAS ]
oxazol-5-yl(4-(5-phenyl-4,5-dihydro-1H-pyrazole-1-carbonyl)piperidin-1-yl)methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 5096 - 5110

51
[ 118994-90-4 ]
N-(3-aminophenyl)-2-bromobenzamide hydrochloride [ No CAS ]
N-[3-(2-bromobenzamido)phenyl]-1,3-oxazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 24h;Sealed tube;	General procedure: To a vial with a magnetic stir bar was added aniline S3 (50.2 mg,0.173 mmol), <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (27 muL, 0.347 mmol), EDC-HCl (33.9 mg, 0.177 mmol), and HOBt (26.7 mg, 0.174). The vial was sealed and flushed with nitrogen for 5 min., then DCE (1.5 mL) and DMF (0.5 mL) were added. To the resulting solution was added a 10% solution of pyridine in DCE (0.14 mL, 0.173 mmol) by syringe, and the reaction was stirred for 24 h. A sample aliquot was taken from the reaction, concentrated under reduced pressure, dissolved in a minimal amount of HPLC grade MeCN, and analyzed by LC-MS to confirm reaction completion. The reaction was then diluted with EtOAc (30 mL)and washed with half-saturated aq. NaHCO3 (3×15 mL), brine (2×10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in a minimal amount of DCM, loaded onto a 10 g silica gel column, and purified by flash chromatography (MeOH:DCM, 0-8%) to give 38 as a yellow oil (40 mg,60%). TLC: mobile phase: MeOH:DCM (6:94), Rf=0.30; LC-MS tR=4.29 min. (Characterization Method A); m/z=387.29 (M+H);1H NMR (300 MHz, CD3OD) delta=8.36 (s, 1H), 8.15 (t, J=2.0 Hz, 1H),7.85 (s, 1H), 7.64 (dd, J=1.0, 7.9 Hz, 1H), 7.53-7.41 (m, 5H),7.41-7.28 (m, 3H); 13C NMR (100 MHz, CD3OD) delta=169.1, 157.2,154.7, 147.0, 140.2, 140.1, 139.3, 134.2, 132.3, 131.2, 130.2, 129.8,128.7, 120.5, 118.5, 118.1, 114.4. HRMS (ESI+) calculated forC17H12BrN3O3 (M+H) 386.0135, found 386.0147.

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3788 - 3796

52
[ 118994-90-4 ]
N-(3-fluoro-5-iodophenyl)-N-methylpiperidin-4-amine hydrochloride [ No CAS ]
(4-((3-fluoro-5-iodophenyl)(methyl)amino)piperidin-1-yl)(oxazol-5-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	A solution of piperidine (050) (50 mg, 0.15 mmol) and <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (25.4 mg, 0.224 mmol) in DMF (2 mL) was charged into a 4 mL vial with a magnetic stir bar. Hunig's Base (0.078 mL, 0.449 mmol), EDC (60.2 mg, 0.314 mmol) and HOBT (48.1 mg, 0.314 mmol) were added. The resulting solution was stirred overnight at room temperature and partitioned between water (10 mL) and EtOAc (10 mL). The solution was extracted with EtOAc (3 x 10 mL), washed with water (10 mL), dried with MgS04, filtered, and evaporated under vacuum. The crude material was dry loaded onto 2 g. silica and purified by column chromatography (ISCO normal phase, 12 g. gold column, 0-20% MeOH/DCM gradient) to isolate (4-((3-fluoro-5- iodophenyl)(methyl)amino)piperidin-l-yl)(oxazol-5-yl)methanone (052) (24 mg, 0.056 mmol, 37%). 1H NMR (400 MHz, CDCL) d ppm 1.68 - 1.85 (m, 2 H) 1.85 - 1.96 (m, 2 (0901) H) 2.77 (s, 3 H) 2.99 - 3.51 (m, 2 H) 3.82 (tt, 7=11.56, 4.06 Hz, 1 H) 4.37 - 5.02 (m, 2 H) 6.45 (dt, 7=12.55, 2.26 Hz, 1 H) 6.81 - 6.87 (m, 1 H) 6.91 (s, 1 H) 7.64 (s, 1 H) 7.96 - 8.00 (m, 1 H). LCMS: 430.3 [M+H]+.

Reference： [1]Patent: WO2019/200100,2019,A1 .Location in patent: Paragraph 00344

53
[ 118994-90-4 ]
2-((2-ethyl-7-methyl-5-(2,6-diazaspiro[3.3]heptan-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(methyl)amino)-4-(4-fluorophenyl)thiazole-5-carbonitrile 2,2,2-trifluoroacetate [ No CAS ]
2-((2-ethyl-7-methyl-5-(6-(oxazole-5-carbonyl)-2,6-diazaspiro[3.3]heptan-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(methyl)amino)-4-(4-fluorophenyl)thiazole-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;	Example 57 2-((2-ethyl-7-methyl-5-(6-(oxazole-5-carbonyl)-2,6-diazaspiro[3.3]heptan-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(methyl)amino)-4-(4-fluorophenyl)thiazole-5-carbonitrile (Compound 57) To a solution of <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (69 mg, 0.61 mmol) and HATU (233 mg, 0.61 mmol) in DCM (5 mL) was added triethylamine (0.7 mL, 5.1 mmol) and 28e (249 mg, 0.51 mmol) at rt. After 2 h, the reaction mixture was quenched with water, diluted with DCM (50 mL), washed with water (2*50 mL), and brine (100 mL). All volatiles were removed under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title Compound 57 (150 mg, 51%). 1H NMR (400 MHz, CDCl3) delta 8.15 (m, 2H), 7.97 (s, 1H), 7.70 (s, 1H), 7.16 (m, 2H), 6.09 (s, 1H), 5.89 (s, 1H), 4.72 (s, 2H), 4.40 (s, 2H), 4.18 (s, 4H), 3.58 (s, 3H), 2.81 (q, 2H), 2.76 (s, 3H), 1.34 (t, 3H). LC-MS (ESI): m/z=583.2 [M+H]+.

Reference： [1]Patent: US2019/367515,2019,A1

54
[ 118994-90-4 ]
2-((4-(trifluoromethyl)phenyl)amino)benzohydrazide [ No CAS ]
N’-(2-((4-(trifluoromethyl)phenyl)amino)benzoyl)oxazole-5-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.1%	With triethylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In N,N-dimethyl-formamide; at 20 - 25℃; for 16h;Inert atmosphere;	To a mixture of 37-la (138.4 mg, 1.22 mmol, 1.2 eq), PYAOP (638.2 mg, 1.22 mmol, 1.2 eq) and TEA (309.6 mg, 3.06 mmol, 425.92 uL, 3 eq) in DMF (3 mL) was added 37-1 (0.3 g, 1.02 mmol, 1 eq) in one portion at 20 C under N2. The mixture was stirred at 20 C for 16 h. LCMS showed 9% of starting material and 15% of desired product was detected. The mixture was diluted with EA (50 mL), washed with brine (15 mL) twice, dried by anhydrous Na2S04, filtered and concentrated to give a residue. The residue was purified by prep-HPLC to give 37-2 (0.04 g, 0.10 mmol, 10.1% yield). LCMS (ESI): RT = 0.749 min, mass calc for C18H13F3N4O3 390.09, m/z found 390.9 [M+l]+. 1H NMR (400 MHz, DMSO-i) d 10.79 (s, 1H), 10.67 (s, 1H), 9.38 (s, 1H), 8.67 (s, 1H), 7.94 (s, 1H), 7.75 (d, J= 8.0 Hz, 1H), 7.59 (d, J= 8.5 Hz, 2H), 7.53 - 7.43 (m, 2H), 7.29 (d, J= 8.5 Hz, 2H), 7.13 - 6.99 (m, 1H).

Reference： [1]Patent: WO2019/222431,2019,A1 .Location in patent: Paragraph 00286

55
[ 118994-90-4 ]
(S,E)-6-amino-N₇-(1-((4-isobutyl- 1H-benzo[d]imidazol-2-yl)methyl)-2-oxo-1,2-dihydropyridin-3-yl)-N₁,N₁-dimethylhept-2-enediamide trifluoroacetate [ No CAS ]
(S,E)-N₇-(1-((4-isobutyl-1H-benzo[d]imidazol-2-yl)methyl)-2-oxo-1,2-dihydropyridin-3-yl)-N₁,N₁-dimethyl-6-(oxazole-5-carboxamido)hept-2-enediamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 25℃; for 16h;	To a solution of (S,E)-6-amino-N7-(1-((4-isobutyl-1H-benzo[d]imidazol-2- yl)methyl)-2-oxo-1,2-dihydropyridin-3-yl)-N1,N1-dimethylhept-2-enediamide (200 mg, 0.337 mmol, TFA) and <strong>[118994-90-4]oxazole-5-carboxylic acid</strong> (57.2 mg, 0.506 mmol) in DMF (2 mL) were added HATU (257 mg, 0.675 mmol) and DIPEA (131 mg, 1.01 mmol) at 0 C. The mixture was stirred at 25 C for 16 h. The reaction mixture was purified by prep-HPLC to give (S,E)-N7-(1-((4-isobutyl-1H-benzo[d]imidazol-2-yl)methyl)-2-oxo-1,2-dihydropyridin- 3-yl)-N1,N1-dimethyl-6-(oxazole-5-carboxamido)hept-2-enediamide (Compound 32) (78.5 mg, 39% yield) as a white solid. LCMS m/z 574.3 (M+1)+.1H NMR (400 MHz, DMSO-d6) d 12.71 (s, 1H), 9.39 (s, 1H), 9.00 (d, J = 7.6 Hz, 1H), 8.59 (s, 1H), 8.25 (dd, J = 7.6, 2.0 Hz, 1H), 7.87 (s, 1H), 7.57 (dd, J = 6.8, 1.6 Hz, 1H), 7.32 (d, J = 7.6 Hz, 1H), 7.08 (t, J = 7.6 Hz, 1H), 6.95 (d, J = 7.2 Hz, 1H), 6.69-6.56 (m, 1H), 6.41-6.31 (m, 2H), 5.50-5.34 (m, 2H), 4.71- 4.58 (m, 1H), 2.95 (s, 3H), 2.81 (s, 3H), 2.76-2.69 (m, 2H), 2.36-2.19 (m, 2H), 2.08-1.77 (m, 3H), 0.88 (d, J = 6.4 Hz, 6H).

Reference： [1]Patent: WO2020/33784,2020,A1 .Location in patent: Paragraph 00332

56
[ 118994-90-4 ]
[ CAS Unavailable ]
[ 1346809-07-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With diphenyl phosphoryl azide; triethylamine for 18h; Inert atmosphere; Reflux;

Reference： [1]Jhaveri, Dishit P.; Osano, Mana; Wipf, Peter [Organic Letters, 2020, vol. 22, # 6, p. 2215 - 2219]

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[ 651059-70-0 ]

Methyl 2-methyloxazole-5-carboxylate

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Methyl 2-aminooxazole-5-carboxylate

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
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

[ CAS No. 118994-90-4 ] {[proInfo.proName]}

Quality Control of [ 118994-90-4 ]

Related Doc. of [ 118994-90-4 ]

Product Details of [ 118994-90-4 ]

Calculated chemistry of [ 118994-90-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 118994-90-4 ]

Application In Synthesis of [ 118994-90-4 ]

[ 118994-90-4 ] Synthesis Path-Upstream 1~1

[ 118994-90-4 ] Synthesis Path-Downstream 1~56

Related Functional Groups of [ 118994-90-4 ]

Carboxylic Acids

Related Parent Nucleus of [ 118994-90-4 ]

Oxazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 118994-90-4 ]

Related Parent Nucleus of
[ 118994-90-4 ]