[ CAS No. 54593-26-9 ] {[proInfo.proName]}

Name: 54593-26-9|3,5-Dimethyl-4-isoxazolecarbaldehyde|98%
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Quality Control of [ 54593-26-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 54593-26-9 ]

Product Details of [ 54593-26-9 ]

CAS No. :	54593-26-9	MDL No. :	MFCD02681977
Formula :	C₆H₇NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TVAYXKLCEILMEA-UHFFFAOYSA-N
M.W :	125.13	Pubchem ID :	289576
Synonyms :

Calculated chemistry of [ 54593-26-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	31.82
TPSA :	43.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	0.63
Log Po/w (WLOGP) :	1.1
Log Po/w (MLOGP) :	-0.25
Log Po/w (SILICOS-IT) :	1.81
Consensus Log Po/w :	0.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.36
Solubility :	5.49 mg/ml ; 0.0439 mol/l
Class :	Very soluble
Log S (Ali) :	-1.11
Solubility :	9.71 mg/ml ; 0.0776 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.92
Solubility :	1.51 mg/ml ; 0.0121 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.57

Safety of [ 54593-26-9 ]

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 [ 54593-26-9 ]

* 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 [ 54593-26-9 ]
Downstream synthetic route of [ 54593-26-9 ]

[ 54593-26-9 ] Synthesis Path-Upstream 1~7

1
[ 19788-36-4 ]
[ 54593-26-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1.16667 h;	To a solution of (3,5-dimethylisoxazol-4-yl)methano3 (1.00 g, 7.86 mmol) in CH₂CI₂ (20 mL) at 0 °C was added Dess-Martin periodinane (4.17 g, 9.83 mmol) over 10 min and the reaction mixture was warmed to rt. The reaction mixture was stirred at rt for 60 min and then filtered through CeHte* and washed through with 0¾¾. The organic layer was dried over N82SO4, concentrated, and purified by column chromatography (15percent EtO Ac/hex anes) to provide the title compound (0.450 g, 46percent). T NMR (400 MHz, DM80-d₆) δ ppm 9.92 (s, 1H), 2.68 (s, 3H), 2.3^' (s, 3H).
46%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1.16667 h;	To a solution of (3,5-dimethylisoxazol-4-yl)methanol (1.00 g, 7.86 mmol) in CH₂CI₂ (20 mL) at 0 °C was added Dess-Martin periodinane (4.17 g, 9.83 mmol) very slowly over 10 min and the reaction mixture was warmed to rt. The reaction mixture was stirred at rt for 60 min and then filtered through Celite^® and washed through with CH₂C1₂. The organic layer was dried over Na₂S0₄, concentrated, and purified by column chromatography (15percent EtOAc/hexanes) to provide the title compound (0.450 g, 46percent). ¾ NMR (400 MHz, DMSO-d₆) δ ppm 9.92 (s, 1H), 2.68 (s, 3H), 2.37 (s, 3H).
45.73%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1.16667 h;	(h) 3,&-dimethvlisoxazoin-4-carbaidehyde: To a solution of (3,5dimethyhsoxazoi-4 yl)methanoi (1.00 g, 7.86 minol) in C]ET2CI2 (20 mE) at 0 °C was added Dess-Martin periodinane (4.17 g, 9.83 inmol) slowly i,,fjthjn 10 nun and the resulting nrixture was warmed to it. The reaction mixture was stirred at rt for 60 mm. After completion of the reaction, the reaction mixture was filtered through Cebte® and washed with Ci-12C12. The organic layer was dried overNa2SO, concentrated, and purified by silica gel colurmi chromatography (15percent EtOAc/Hexanes) to provide the title compound (0.450 g, 45.73 percent). ‘H NMR (400 MHz, DMSO-d6) 3 ppm 9.92 (s, I H), 2.68 (s, 3 H), 2.37 (s. 3 H).

37%

With manganese dioxide In dichloromethane

Example 39
Preparation of 3,5-dimethylisoxazole-4-carboxaldehyde
Manganese dioxide (5.48 g, 62.9 mmol) and dichloromethane (20 mL) were added to a solution of 3,5-dimethylisoxazole-4-methanol prepared according to the literature procedure: Saucy, G.; Scott, J. W. U.S. Pat. No. 3,984,428 Oct. 5, 1976; 1.00 g, 7.9 mmol) in dichloromethane (25 mL).
The mixture was stirred at room temperature overnight, then filtered through Celite.(R)., evaporated under reduced pressure and the residual material was chromatographed over silica gel (10percent ethyl acetate/hexanes) to give 3,5-dimethylisoxazole-4-carboxaldehyde (365 mg, 37percent yield) as a colorless solid.

Reference： [1] Organic Preparations and Procedures International, 2003, vol. 35, # 2, p. 207 - 214
[2] Synthetic Communications, 1983, vol. 13, # 10, p. 817 - 822
[3] Patent: WO2013/19635, 2013, A1, . Location in patent: Page/Page column 71
[4] Patent: WO2013/19682, 2013, A1, . Location in patent: Page/Page column 92
[5] Patent: WO2013/19626, 2013, A1, . Location in patent: Page/Page column 26
[6] Patent: US2002/161237, 2002, A1,
[7] Patent: EP1186604, 2002, A1, . Location in patent: Page 108

2
[ 201008-69-7 ]
[ 54593-26-9 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 50, p. 17151 - 17162

3
[ 2510-36-3 ]
[ 54593-26-9 ]

Reference： [1] Synthetic Communications, 1983, vol. 13, # 10, p. 817 - 822
[2] Patent: WO2013/19635, 2013, A1,
[3] Patent: WO2013/19682, 2013, A1,
[4] Patent: WO2013/19626, 2013, A1,

4
[ 56328-87-1 ]
[ 54593-26-9 ]

Reference： [1] Patent: WO2013/19635, 2013, A1,
[2] Patent: WO2013/19682, 2013, A1,
[3] Patent: WO2013/19626, 2013, A1,

5
[ 100596-16-5 ]
[ 54593-26-9 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 50, p. 17151 - 17162

6
[ 55727-23-6 ]
[ 54593-26-9 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 50, p. 17151 - 17162

7
[ 300-87-8 ]
[ 54593-26-9 ]

Reference： [1] Patent: EP1186604, 2002, A1,

[ 54593-26-9 ] Synthesis Path-Downstream 1~88

1
[ 54593-26-9 ]
[ 1530-45-6 ]
[ 81190-82-1 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 711 - 722

2
[ 54593-26-9 ]
[ 1826-67-1 ]
[ 110773-98-3 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 5501 - 5505

3
[ 54593-26-9 ]
phenylmagnesium bromide [ No CAS ]
[ 39511-14-3 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4011 - 4019
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2519 - 2525

4
[ 54593-26-9 ]
[ 141-97-9 ]
[ 87967-96-2 ]

Reference： [1]Organic Preparations and Procedures International,2003,vol. 35,p. 207 - 214
[2]Synthetic Communications,1983,vol. 13,p. 817 - 822

5
[ 54593-26-9 ]
[ 105-45-3 ]
[ 100-46-9 ]
[ 107378-04-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 711 - 713

6
[ 54593-26-9 ]
[ 1118-61-2 ]
4-(3,5-Dimethyl-isoxazol-4-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbonitrile [ No CAS ]

Reference： [1]Magnetic Resonance in Chemistry,1996,vol. 34,p. 495 - 504

7
[ 201008-69-7 ]
[ 54593-26-9 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 17151 - 17162

9
[ 14282-76-9 ]
[ 54593-26-9 ]
(3,5-dimethyl-isoxazol-4-yl)-(3-methyl-thiophen-2-yl)-methanol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2519 - 2525

10
[ 866788-63-8 ]
[ 54593-26-9 ]
(E)-3-(3,5-dimethylisoxazol-4-yl)acrylic acid 4'-[(E)-3-(3,5-dimethylisoxazol-4-yl)acryloyloxymethyl]-[2,2']bipyridinyl-4-ylmethyl ester [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 3140 - 3160

11
[ 54593-26-9 ]
[ 1003583-71-8 ]
1-(3,4-dichlorobenzyl)-3-(4-((((3,5-dimethylisoxazol-4-yl)methyl)(methyl)amino)methyl)thiazol-2-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 133 l-(3,4-Dichlorobenzyl)-3-(4-((((3,5-dimethylisoxazol-4-yl)methyl)(methyl) amino)methyI)thiazol-2-yl)urea; [00230] Sodium triacetoxyborohydride (86 mg, 0.4 mmol, 2.0 eq) was added to a dichloromethane (2 mL) solution of l-(3,4-Dichloro-benzyl)-3-(4-methylaminomethyl- thiazol-2-yl)-urea (Example 132, 70 mg, 0.2 mmol) and 3,5-dimethylisoxazole-4- carbaldehyde (33 mg,0.25 mmol, 1.25 eq). After 16 hours of stirring, methanol (1 mL) and aqueous HCl (0.5 mL, IN) were added. The mixture was neutralized with dilute NaHCO3 solution. An aqueous work-up with dichloromethane and a chromatography (silica 0-3% <n="69"/>MeOH in CH2Cl2) afforded the title compound. 1H NMR (400 MHz, CDCl3): delta 7.36 (m, 2H), 7.10 (dd, IH), 6.64 (s, IH), 4.32 (d, 2H), 3.46 (s, 3H), 3.21 (s, 3H), 2.28 (s, 3H), 2.16 (s, 3H), 2.07 (s, 3H). MS (ES+): M/Z 454 (M+ 1).

Reference： [1]Patent: WO2008/11191,2008,A1 .Location in patent: Page/Page column 67-68

12
[ 54593-26-9 ]
1-(3-fluoro-benzyl)-3-(3-methylaminomethyl-[1,2,4]thiadiazol-5-yl)-urea [ No CAS ]
1-(3-[(3,5-dimethyl-isoxazol-4-ylmethyl)-methyl-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-3-(3-fluoro-benzyl)-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 170 l-(3-{((3,5-Dimethyl-isoxazol-4-ylmethyl)-methyl-amino]-methyl}-[l,2,4]thiadiazol-5- yl)-3-(3-fluoro-benzyl)-urea;[00276] l-(3-Fluoro-benzyl)-3-(3-methylaminomethyl-[l,2,4]thiadiazol-5-yl)-urea(Intermediate XXVII) was taken up in DCM and methanol with 3,5-Dimethyl-isoxazole-4- carbaldehyde (2 eq.) and acetic acid (several drops). Reaction was stirred for several hours at ambient temperature. Sodium cyanoborohydride (2 eq.) was added at once and the reaction was stirred overnight at ambient temperature. An additional equivalent of 3,5-Dimethyl- isoxazole-4-carbaldehyde and sodium cyanoborohydride (2 eq.) was added and stirred 4 more <n="80"/>hours. Crude rxn mixture was loaded directly onto a silica plug and eluted with 10% saturated NH3/MeOH in DCM. Purified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3) to give the title compound. 1H NMR (400 MHz, DMSO): delta 1 1.45 (br s, IH), 7.43-7.35 (m, 2H), 7.17-7.05 (m, 3H), 4.38 (d, 2H), 3.58 (s, 2H), 3.33 (s, 2H), 2.31 (s, 3H), 2.16 (s, 3H), 2.15 (s, 3H).

Reference： [1]Patent: WO2008/11191,2008,A1 .Location in patent: Page/Page column 78-79

13
[ 54593-26-9 ]
[ 93548-06-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2519 - 2525

14
[ 54593-26-9 ]
4-[chloro-(3-methyl-thiophen-2-yl)-methyl]-3,5-dimethyl-isoxazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2519 - 2525

15
[ 54593-26-9 ]
1-[(3,5-dimethyl-isoxazol-4-yl)-phenyl-methyl]-piperazine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2519 - 2525

16
[ 54593-26-9 ]
1-[(3,5-dimethyl-isoxazol-4-yl)-(3-methyl-thiophen-2-yl)-methyl]-piperazine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2519 - 2525

17
[ 54593-26-9 ]
3,5-dimethyl-4-phenyl[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazino]methylisoxazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2519 - 2525

18
[ 54593-26-9 ]
4-{4-[(3,5-dimethyl-isoxazol-4-yl)-(3-methyl-thiophen-2-yl)-methyl]-piperazin-1-yl}-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2519 - 2525

19
[ 54593-26-9 ]
[ 556782-39-9 ]

Reference： [1]Organic Preparations and Procedures International,2003,vol. 35,p. 207 - 214

20
[ 54593-26-9 ]
2-phentlthiomethyl-6-methyl-3,5-dicarboethoxy-4-(3,5-dimethyl-4-isoxazolyl)-1,4-dihydropyridine [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2003,vol. 35,p. 207 - 214

21
[ 54593-26-9 ]
4-(3,5-dimethyl-isoxazol-4-yl)-2-methyl-6-(1-methyl-1H-imidazol-2-ylsulfanylmethyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2003,vol. 35,p. 207 - 214

22
[ 54593-26-9 ]
4-(3,5-dimethyl-isoxazol-4-yl)-2-methyl-6-(naphthalen-2-yloxymethyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2003,vol. 35,p. 207 - 214

23
[ 100596-16-5 ]
[ 54593-26-9 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 17151 - 17162

24
[ 123-54-6 ]
CH₃CH₂CH=CHCH₂CH₂-halide [ No CAS ]
[ 54593-26-9 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 17151 - 17162

25
[ 55727-23-6 ]
[ 54593-26-9 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 17151 - 17162

26
[ 54593-26-9 ]
[ 653579-56-7 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 5501 - 5505

27
[ 54593-26-9 ]
[ 110774-00-0 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 5501 - 5505

28
[ 54593-26-9 ]
[ 110773-86-9 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 5501 - 5505
[2]Journal of Organic Chemistry,1987,vol. 52,p. 5501 - 5505

29
[ 54593-26-9 ]
[ 110773-93-8 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 5501 - 5505

30
[ 54593-26-9 ]
[ 110773-92-7 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 5501 - 5505

31
[ 2510-36-3 ]
[ 54593-26-9 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 817 - 822
[2]Patent: WO2013/19635,2013,A1
[3]Patent: WO2013/19682,2013,A1
[4]Patent: WO2013/19626,2013,A1

32
[ 54593-26-9 ]
[ 27428-42-8 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 711 - 722

33
[ 54593-26-9 ]
[ 129975-10-6 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 711 - 722

34
[ 54593-26-9 ]
[ 135510-62-2 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 711 - 722

35
[ 54593-26-9 ]
[ 135510-61-1 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 711 - 722

36
[ 54593-26-9 ]
[ 135510-64-4 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 711 - 722

37
[ 54593-26-9 ]
[ 135510-59-7 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 711 - 722

38
[ 54593-26-9 ]
[ 135510-63-3 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 711 - 722

39
[ 54593-26-9 ]
[ 31301-47-0 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4011 - 4019

40
[ 54593-26-9 ]
[ 127916-10-3 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4011 - 4019

41
[ 54593-26-9 ]
[ 313750-60-6 ]
methyl 7-(4-butoxyethoxyphenyl)-1-[(3,5-dimethylisoxazol-4-yl)methyl]-2,3-dihydro-1-benzazepine-4-carboxylate [ No CAS ]

Reference： [1]Patent: EP1186604,2002,A1 .Location in patent: Page 108

42
[ 54593-26-9 ]
2-(3-fluoro-phenyl)-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine [ No CAS ]
5-[4-(3,5-dimethyl-isoxazol-4-ylmethyl)-piperazin-1-yl]-2-(3-fluoro-phenyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 18.5h;	2-(3-Fluoro-phenyl)-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.15 mmol) was dissolved in 4 mL OF CH2Cl2 along with 2 eq. of 3,5-dimethyl-isoxazole-4-carbaldehyde and 25 mL of glacial acetic acid. The reaction mixture was stirred at room temperature for 30 minutes and sodium triacetoxyborohydride (4 eq. ) was added in a single portion. The resulting reaction mixture was then stirred at room temperature for 18 hours. It was then concentrated under a stream of N2 and purified by preparative HPLC using a mixture of aqueous CH3CN that has been buffered with 0.1 % TFA. 1H NMR (DMSO-d6) delta 6.9-7.25 (m, 3 H), 3.8 (br s, 2 H), 2.2-3.2 (m, 8H), 1.6 (br s, 6H). MS: M/Z : 424 [M + H] +.

Reference： [1]Patent: WO2004/92170,2004,A2 .Location in patent: Page 27; 28

43
[ 54593-26-9 ]
[ 23834-14-2 ]
C₁₅H₁₃ClN₄O [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 1333 - 1343

44
[ 54593-26-9 ]
[ 81290-20-2 ]
C₁₀H₁₆F₃NO₂Si [ No CAS ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 6611 - 6625

45
[ 300-87-8 ]
[ 54593-26-9 ]

Reference： [1]Patent: EP1186604,2002,A1

46
[ 54593-26-9 ]
C₂₉H₃₃ClN₂O₄ [ No CAS ]

Reference： [1]Patent: EP1186604,2002,A1

47
[ 54593-26-9 ]
7-(4-butoxyethoxyphenyl)-1-[(3,5-dimethylisoxazol-4-yl)methyl]-2,3-dihydro-1-benzazepine-4-carboxylic acid [ No CAS ]

Reference： [1]Patent: EP1186604,2002,A1

48
[ 54593-26-9 ]
7-(4-butoxyethoxyphenyl)-1-[(3,5-dimethylisoxazol-4-yl)methyl]-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide [ No CAS ]

Reference： [1]Patent: EP1186604,2002,A1

49
[ 54593-26-9 ]
[ 75-16-1 ]
[ 59402-44-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 1.66667h;	To a solution of <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (0.450 g, 0.36 mmol) in dry THF (3 mL) at 0 C was added MeMgBr (3.0 M solution in Et20) (1.2 mL, 3.60 mmol) dropwise over 10 min and the reaciion mixture was warmed to rt. The reaction mixture was stirred at rt for 90 min. Water ( 10 mL) was added very slowly and ihe reaciion mixture was extracted wiih EtO Ac ( 100 rnL). The organic layer was dried over Na2SQ4, concentrated, and purified by column chromatography (27% EtOAc/hexanes) to provide the title compound (0,480 g, 95%). NMR (400 MHz, DMSO-de) delta ppm 5.07 (d, 1H), 4.65 - 4.70 (m, IH), 2.33 (s, 3H), 2.20 (s, 3H), 1.32 (d, 3H).
95%		To a solution of <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (0.450 g, 0.36 mmol) in dry THF (3 mL) at 0 C was added MeMgBr (3.0 M solution in Et20) (1.2 mL, 3.60 mmol) dropwise over 10 min and the reaction mixture was warmed to rt. The reaction mixture was stirred at rt for 90 min. Water (10 mL) was added very slowly and the reaction mixture was extracted with EtOAc (100 mL). The organic layer was dried over Na2S04, concentrated, and purified by column chromatography (27% EtOAc/hexanes) to provide the title compound (0.480 g, 95%). H NMR (400 MHz, DMSO-d6) delta ppm 5.07 (d, 1H), 4.65 - 4.70 (m, 1H), 2.33 (s, 3H), 2.20 (s, 3H), 1.32 (d, 3H).

Reference： [1]Patent: WO2013/19635,2013,A1 .Location in patent: Page/Page column 71-72
[2]Patent: WO2013/19682,2013,A1 .Location in patent: Page/Page column 92; 93

50
[ 56328-87-1 ]
[ 54593-26-9 ]

Reference： [1]Patent: WO2013/19635,2013,A1
[2]Patent: WO2013/19682,2013,A1
[3]Patent: WO2013/19626,2013,A1

51
[ 54593-26-9 ]
[ 1421838-38-1 ]

Reference： [1]Patent: WO2013/19635,2013,A1

52
[ 54593-26-9 ]
[ 1421838-41-6 ]

Reference： [1]Patent: WO2013/19635,2013,A1

53
[ 54593-26-9 ]
[ 1421837-32-2 ]

Reference： [1]Patent: WO2013/19635,2013,A1

54
[ 54593-26-9 ]
[ 1421838-42-7 ]

Reference： [1]Patent: WO2013/19635,2013,A1

55
[ 54593-26-9 ]
[ 1421837-91-3 ]

Reference： [1]Patent: WO2013/19635,2013,A1

56
[ 54593-26-9 ]
[ 35166-20-2 ]

Reference： [1]Patent: WO2013/19635,2013,A1
[2]Patent: WO2013/19682,2013,A1

57
[ 54593-26-9 ]
[ 1402652-24-7 ]

Reference： [1]Patent: WO2013/19635,2013,A1
[2]Patent: WO2013/19682,2013,A1

58
[ 54593-26-9 ]
[ 1421838-37-0 ]

Reference： [1]Patent: WO2013/19635,2013,A1

59
[ 54593-26-9 ]
[ 1422169-60-5 ]

Reference： [1]Patent: WO2013/19682,2013,A1

60
[ 54593-26-9 ]
[ 1421948-85-7 ]

Reference： [1]Patent: WO2013/19682,2013,A1

61
[ 54593-26-9 ]
[ 1421949-06-5 ]

Reference： [1]Patent: WO2013/19682,2013,A1
[2]Patent: WO2013/19626,2013,A1

62
[ 54593-26-9 ]
[ 1421949-03-2 ]
[ 1421949-05-4 ]

Yield	Reaction Conditions	Operation in experiment
38%		2-(2-((3,5-dimethylisoxazol-4-yl)(ethoxy)methyl)benzofuran-5-yl)-N-((2,4- dimethylphenyl)(phenyl)methyl)acetamidea) methyl 2-(2-((3,5-dimethylisoxazol-4-yl)(hydroxy)methyl)benzofuran-5-yl)acetateTo a solution of methyl 2-(2-bromobenzofuran-5-yl)acetate (2.0 mg, 7.46 mmol) in THF (50 mL) at 0 C was added z-PrMgCl (5.6 mL, 1 1.2 mmol, 2 N in THF). The reaction mixture was stirred at 0 C for 30 min. <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (1.5 g, 12 mmol) was added and the reaction mixture was stirred for 2 h. Saturated NH4C1 (10 mL) was added and the reaction mixture was extracted with EtO Ac (3 x 50 mL). The combined organic layers were washed with brine (3 x 15 mL), dried over Na2S04, filtered, and concentrated. The resultant residue was purified by column chromatography (30% EtO Ac/petroleum ether) to afford the title compound (900 mg, 38%) as a yellow oil. LCMS-P 1 : 316 [M+H]+; Rt: 1.481 min.
38%		(i) methyl 2-(2-((3,5-dimethylisoxazoi-4-yl)(hydroxy)methyl)benzofuran-Syl)acetate: To a solution of methyl 2?(2-brornoberizofuran-5-yl)acetate (2.0 mg, 7.46 nmmnol) in. 50 niL TI-IF at 0 Cwas added i-PrMgC1 (5.6 mE, 11.2 mniol, 2N in THF). The mixture was stirred at 0 C for 30 mm. Then 3,Sdimethylisoxazole4-carbaldehyde (1.5 g, 12 mmol) was added to the mixture. The resulting mixture was stirred for 2 h. Saturated aq. NHCi (10 mL) was added to the mixture and the mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (3 x 15 mL) and dried over Na2504. The solvent was evaporated to aresidue which was purified by silica gel column chromatography (30% EtOAc/petroleum ether) to afford the title compound (900 mg, yield 38%) as a yellow oil. LCMS-P1: 316 [M+H] R = i.48i mm.

Reference： [1]Patent: WO2013/19682,2013,A1 .Location in patent: Page/Page column 98; 99
[2]Patent: WO2013/19626,2013,A1 .Location in patent: Page/Page column 26

63
[ 54593-26-9 ]
2-(2-((R)-(3,5-dimethylisoxazol-4-yl)(hydroxy)methyl)benzofuran-5-yl)-N-((R)-(2,4-dimethylphenyl)(phenyl)methyl)acetamide [ No CAS ]
2-(2-((S)-(3,5-dimethylisoxazol-4-yl)(hydroxy)methyl)benzofuran-5-yl)-N-((R)-(2,4-dimethylphenyl)(phenyl)methyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2013/19626,2013,A1

64
[ 54593-26-9 ]
[ 1421949-53-2 ]

Reference： [1]Patent: WO2013/19626,2013,A1

65
[ 54593-26-9 ]
[ 1600562-81-9 ]
[ 1600563-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 1h;Inert atmosphere; Cooling with acetone-dry ice;	THF (5 mL) was added to a mixture of 6-bromo-2,4-dichloro-3-phenylquinoline (363 mg, 1.03 mmol, Intermediate 1, step c) and <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (180 mg, 1.44 mmol) under a nitrogen atmosphere. The resulting colorless solution was cooled in a dry ice/acetone bath. n-BuLi (1.6 M in hexane, 0.771 mL, 1.23 mmol) was added dropwise and the mixture was stirred at -78 C. for 30 min, then moved to an ice bath and stirred for 30 min. The reaction was quenched by addition of saturated aqueous NH4Cl and was diluted with water. The mixture was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated to afford crude (2,4-dichloro-3-phenylquinolin-6-yl)(3,5-dimethylisoxazol-4-yl)methanol which was used without further purification in the next step. 1,4-dioxane (7.5 mL) and manganese (IV) dioxide (447 mg, 5.14 mmol) were added to the crude alcohol from the prior step. The resulting black suspension was heated in a 100 C. oil bath in a sealed tube overnight. The mixture was allowed to cool, was diluted with DCM, and was filtered through Celite. The filtrate was concentrated and the residue was purified by flash column chromatography-(silica gel, 3-15% EtOAc-heptane) to isolate the title compound.
		THF (5 mL) was added to a mixture of 6-bromo-2,4-dichloro-3-phenylquinoline (363 mg, 1.03 mmol, Intermediate 1: step c) and <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (180 mg, 1.44 mmol) under a nitrogen atmosphere. The resulting colorless solution was cooled in a dry ice/acetone bath. n-BuLi (1.6 M in hexane, 0.77 mL, 1.23 mmol) was added dropwise and the mixture was stirred at -78 C. for 30 minutes, then moved to an ice bath and stirred for 30 minutes. The reaction was quenched by addition of saturated aqueous NH4Cl and was diluted with water. The mixture was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated to afford the crude title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.35 (s, 1H), 8.04 (d, J=8.80 Hz, 1H), 7.74 (dd, J=1.71, 8.80 Hz, 1H), 7.48-7.62 (m, 3H), 7.35-7.48 (m, 2H), 6.25 (d, J=4.16 Hz, 1H), 5.99 (d, J=3.42 Hz, 1H), 2.37 (s, 3H), 1.99 (s, 3H); MS m/e 398.9 (M+H)+.
	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 1h;Inert atmosphere;	Example 1: (2,4-Dichloro-3-phenylquinolin-6-yl)(3,5-dimethylisoxazol-4-yl)methanolTHF (5 mL) was added to a mixture of 6-bromo-2,4-dichloro-3-phenylquinoline (363 mg, 1.03 mmol, Intermediate 1 : step c) and 3,5-dimefhyiisoxazole-4-carbaldehyde (1 80 mg, 1.44 mmol) under a nitrogen atmosphere. The resulting colorless solution was cooled in a dry ice/acetone bath. n-BuLi (1.6 M in hexane, 0.77 mL, 1.23 mmol) was added dropwise and the mixture was stirred at -78 C for 30 minutes, then moved to an ice bath and stirred for 30 minutes. The reaction was quenched by addition of saturated aqueous NH4Cl and was diluted with water. The mixture was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated to afford the crude title compound, 1H NMR (400 MHz, DMSO-d6) delta ppm 8.35 (s, 1H), 8.04 (d, J = 8.80 Hz, 1H), 7,74 (dd, J = 1.71 , 8.80 Hz, 1H), 7,48 - 7.62 (m, 3H), 7.35 - 7.48 (m, 2H), 6.25 (d, J = 4, 16 Hz, 1H), 5,99 (d, J = 3.42 Hz, 1H), 2.37 (s, 3H), 1 .99 (s, 3H); MS m/e 398.9 (M+H)+.

With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 1h;Inert atmosphere; Cooling with acetone-dry ice;

THF (5 mL) under a nitrogen atmosphere, 6-bromo-2,4-di-chloro-3-phenyl-quinoline (363 mg, 1.03 mmol, Intermediate 1: step c) and 3,5-dimethyl-isoxazol -4 - carbaldehyde (180 mg, 1.44 mmol)It was added to a mixture of. The resulting colorless solution was cooled in a dry ice / acetone bath.n-BuLi was stirred (1.6 M, 0.77 mL, 1.23 mmol in hexane) was added dropwise to the 30 minutes to the mixture at -78 then, transferred to an ice bath and stirred for 30 minutes. The reaction was quenched by the addition of saturated NH4Cl solution, and diluted with water. The mixture was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated to give the crude title compound

Reference： [1]Patent: US2014/107097,2014,A1 .Location in patent: Paragraph 0366; 0367
[2]Patent: US2015/105372,2015,A1 .Location in patent: Paragraph 0306; 0307
[3]Patent: WO2015/57206,2015,A1 .Location in patent: Page/Page column 75
[4]Patent: KR2016/68948,2016,A .Location in patent: Paragraph 0406-0408

66
[ 54593-26-9 ]
[ 1599529-50-6 ]
(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline-6-yl)(3,5-dimethylisoxazol-4-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (2.0 g, 4.64 mmol, Intermediate 10: step d) was added THF (65 mL) at room temperature which resulted in a colorless homogeneous mixture. The solution was cooled to -70 C. which remained homogeneous and then n-BuLi (2.5 M in hexanes, 2.1 mL, 5.25 mmol) was added dropwise. The color of the solution became a dark opaque reddish-brown color. After 2 minutes, <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (705 mg, 5.63 mmol in 2 mL THF) was introduced. The reaction mixture immediately became a homogeneous yellow solution. After 25 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous layer was extracted with EtOAc (3*50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to afford a faint yellow oil. FCC on silica gel (100% DCM increasing to 20% CH3CN-DCM) afforded the title compound as an off white amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.17 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.56-7.48 (m, 3H), 7.39 (d, J=8.1 Hz, 2H), 5.96 (d, J=3.2 Hz, 1H), 4.35 (s, 2H), 4.07 (s, 3H), 2.34 (s, 3H), 2.32 (br. s, 1H), 2.10 (s, 3H). MS (ESI): mass calcd. for C24H20ClF3N2O3, 476.1; m/z found, 476.9 [M+H]+.
		Example 20a: (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(3,5-dimethylisoxazol-4-yl)methanolTo a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (2.0 g, 4.64 mmol, intermediate 10: step d) was added THF (65 mL) at room temperature which resulted in a colorless homogeneous mixture. The solution was cooled to -70 C which remained homogeneous and then n-BuLi (2.5 M in hexanes, 2.5 mL, 5.25 mmol) was added dropwise. The color of the solution became a dark opaque reddish-brown color. After 2 minutes, <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (705 mg, 5.63 mmol in 2 mL THF) was introduced. The reaction mixture immediately became a homogeneous yellow solution. After 25 minutes the reaction mixture was quenched with aqueous NH4CI solution and the aqueous layer was extracted with EtOAc (3 x 50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to afford a faint yellow oil. FCC on silica gel (100% DCM increasing to 20% CH3CN-DCM) afforded the title compound as an off white amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.17 (s, 1H), 7.82 (d, J= 8.6 Hz, 1H), 7.56 - 7.48 (m, 3H), 7.39 (d, J = 8.1 Hz, 2H), 5.96 (d, J = 3.2 Hz, 1H), 4.35 (s, 2H), 4.07 (s, 3H), 2.34 (s, 3H), 2.32 (br. s, 1H), 2.10 (s, 3H). MS (ESI): mass calcd. for C24H20ClF3N2O3, 476.1; m/z found, 476.9 [M+H]+. Example 20a was purified by chiral SFC (Stationary phase: Chiralpak AD-H 5 mum 250 x 20 mm, Mobile phase: 70% C02, 30% mixture of MeOH/i-PrOH (50/50 v/v). The first eluting enantiomer was Example 20b and the second eluting enantiomer was Example 20c.
		To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (2.0 g, 4.64 mmol, Intermediate 12: step d) was added THF (65 mL) and the solution was cooled to -78 C. n-BuLi (2.5 M in hexanes, 2.1 mL, 5.25 mmol) was added dropwise producing a dark reddish-brown mixture. After 2 minutes, a THF solution of <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (700 mg, 5.63 mmol in 2 mL THF) was introduced. The reaction mixture immediately became a homogeneous yellow solution. After 25 minutes the mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc (3*50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to dryness. Chromatography on silica gel (100% DCM increasing to 20% CH3CN/DCM) provided the titled compound an off white amorphous solid.

		Intermediate 63: step a (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(3,5-dimethylisoxazol-4-yl)methanol To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoiine (2.0 g, 4.64 nimol, Intermediate 12: step d) was added THF (65 mL) and the solution was cooled to - 78 C. w-BuLi (2,5 M in hexanes, 2.1 mL, 5,25 mmol) was added dropwise producing a dark reddish-brown mixture. After 2 minutes, a. THF solution of 3,5-dimethylisoxazole-4- carbaldehyde (700 mg, 5.63 mmol in 2 mL THF) was introduced. The reaction mixture immediately became a homogeneous yellow solution. After 25 minutes the mixture was quenched with aqueous NH4CI solution and the aqueous portion was extracted with EtOAc (3 x 50 mL). The combined organics were washed with brine, dried over MgS04, filtered and concentrated to dryness. Chromatography on silica gel (100% DCM increasing to 20% CH3CN/DCM) provided the titled compound an off white amorphous solid.
		At room temperature for 6-bromo-4-chloro-2-methoxy-3 - (4 - (trifluoromethyl) benzyl) quinoline (2.0 g, 4.64 mmol, Intermediate 10: step d) comprises that the flask, THF It was added (65 mL) to obtain a colorless, homogeneous mixture.The solution cooled to -70 , to maintain a uniform state was Next,n-BuLi(hexane of 2.5 M, 2.1 mL, 5.25 mmol) was the added dropwise.The color of the solution became a dark reddish brown opaque.After two minutes, was introduced 3,5-dimethyl-isoxazole-4-carbaldehyde (705 mg, mmol of 5.63, 2 mL THF).The reaction mixture was immediately uniform yellow solution.After 25 minutes, the reaction mixture NH4quenched with Cl solution, and extracted the aqueous portion with EtOAc (3 × 50 mL).The combined organics were washed with brine, MgSO4dried, filtered, and concentrated to give a pale yellow oil.Silica gel (100% DCM, 20% CH3CN-DCM as increased) on the FCC in by, yellow-white amorphous solid as the title compound was obtained.

Reference： [1]Patent: US2015/105372,2015,A1 .Location in patent: Paragraph 0346; 0347
[2]Patent: WO2015/57206,2015,A1 .Location in patent: Page/Page column 89
[3]Patent: US2015/105366,2015,A1 .Location in patent: Paragraph 0499; 0500
[4]Patent: WO2015/57205,2015,A1 .Location in patent: Page/Page column 138; 139
[5]Patent: KR2016/68948,2016,A .Location in patent: Paragraph 0465-0467

67
[ 54593-26-9 ]
[ 1599529-50-6 ]
(S)-(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(3,5-dimethylisoxazol-4-yl)methanol [ No CAS ]
(R)-(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(3,5-dimethylisoxazol-4-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (2.0 g, 4.64 mmol, Intermediate 10: step d) was added THF (65 mL) at room temperature which resulted in a colorless homogeneous mixture. The solution was cooled to -70 C. which remained homogeneous and then n-BuLi (2.5 M in hexanes, 2.1 mL, 5.25 mmol) was added dropwise. The color of the solution became a dark opaque reddish-brown color. After 2 minutes, <strong>[54593-26-9]3,5-dimethylisoxazole-4-carbaldehyde</strong> (705 mg, 5.63 mmol in 2 mL THF) was introduced. The reaction mixture immediately became a homogeneous yellow solution. After 25 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous layer was extracted with EtOAc (3*50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to afford a faint yellow oil. FCC on silica gel (100% DCM increasing to 20% CH3CN-DCM) afforded the title compound as an off white amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.17 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.56-7.48 (m, 3H), 7.39 (d, J=8.1 Hz, 2H), 5.96 (d, J=3.2 Hz, 1H), 4.35 (s, 2H), 4.07 (s, 3H), 2.34 (s, 3H), 2.32 (br. s, 1H), 2.10 (s, 3H). MS (ESI): mass calcd. for C24H20ClF3N2O3, 476.1; m/z found, 476.9 [M+H]+.

Reference： [1]Patent: US2015/105372,2015,A1 .Location in patent: Paragraph 0346; 0347

68
[ 54593-26-9 ]
[ 1475-91-8 ]
(1E,4E)-1,5-bis(3,5-dimethylisoxazol-4-yl)penta-1,4-dien-3-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 4713 - 4726

69
[ 54593-26-9 ]
1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one [ No CAS ]
1-(3,5-dimethylisoxazol-4-yl)-3-(triisopropylsilyl)prop-2-yn-1-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 8745 - 8749

70
[ 4319-49-7 ]
[ 54593-26-9 ]
C₁₀H₁₅N₃O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 2939 - 2943
Angew. Chem.,2016,vol. 128,p. 2992 - 2996,5

71
[ 54593-26-9 ]
C₁₄H₁₉F₂N₃O₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 2939 - 2943
Angew. Chem.,2016,vol. 128,p. 2992 - 2996,5

72
[ 54593-26-9 ]
methyl 2-((3-benzyl-5-phenylpyrazin-2-yl)amino)-2-(diethoxyphosphoryl)acetate [ No CAS ]
C₂₅H₂₀N₄O₂ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 10369 - 10375

73
[ 54593-26-9 ]
[ 7677-24-9 ]
2-(3,5-dimethylisoxazol-4-yl)-2-hydroxyacetonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 3325 - 3349

74
[ 54593-26-9 ]
2-amino-1-(3,5-dimethylisoxazol-4-yl)ethanol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 3325 - 3349

75
[ 54593-26-9 ]
tert-butyl (2-(3,5-dimethylisoxazol-4-yl)-2-hydroxyethyl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 3325 - 3349

76
[ 54593-26-9 ]
tert-butyl (2-azido-2-(3,5-dimethylisoxazol-4-yl)ethyl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 3325 - 3349

77
[ 54593-26-9 ]
2-azido-2-(3,5-dimethylisoxazol-4-yl)ethanamine trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 3325 - 3349

78
[ 54593-26-9 ]
(3R)-3-((7-((2-azido-2-(3,5-dimethylisoxazol-4-yl)ethyl)amino)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)amino)-3-(3-chlorophenyl)propanenitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 3325 - 3349

79
[ 54593-26-9 ]
(R)-3-((7-(((S)-2-amino-2-(3,5-dimethylisoxazol-4-yl)ethyl)amino)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)amino)-3-(3-chlorophenyl)propanenitrile [ No CAS ]
(R)-3-((7-(((R)-2-amino-2-(3,5-dimethylisoxazol-4-yl)ethyl)amino)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)amino)-3-(3-chlorophenyl)propanenitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 3325 - 3349

80
[ 54593-26-9 ]
[ 19335-11-6 ]
[ 108-94-1 ]
3,5-dimethyl-4-(8,9,10,11-tetrahydro-3H-pyrazolo[4,3-a]phenanthridin-7-yl)isoxazole [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 4521 - 4524

81
[ 54593-26-9 ]
N-[4-methyl-2-(piperidin-1-yl)phenyl](5-methylfuran-2-yl)methyl}-2-(2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide [ No CAS ]
2-{3-[(dimethyl-1,2-oxazol-4-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-5-yl}-N-[4-methyl-2-(piperidin-1-yl)phenyl](5-methylfuran-2-yl)methyl}acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With piperidine; In ethanol; at 80℃;	To a solution of previously synthesized N-[4-methyl-2- (piperid in-i -yl)phenyl](5-methylfuran-2-yl)methyl}-2-(2-oxo- 2,3-dihydro-i H-indol-5-yl)acetamide Cpd.24 (75 mg, 0.16 mmol) and 3,5-dimethyl-i ,2-oxazole-4-carbaldehyde (25 mg, 0.20 mmol) in EtOH (2 mL) was added few drops ofcatalytic piperidine. The reaction mixture was heated at080 C overnight. The solvents were removed under reducedpressure. The crude material was purified by silica gelcolumn chromatography using CH2CI2/MeOH (95:5) aseluent to afford 2-{3-[(dimethyl-i 2-oxazol-4-yl)methylidene]-2-oxo-2,3-dihydro-i H-indol-5-yl}-N-[4-methyl-2-(piperidin-i-yl)phenyl](5-methylfuran-2-yl)methyl}acetamide (80 mg, 86%) as yellow solid, mp:128C1H NMR (300 MHz, din ppm): 1.40-i .54 (m, 6H), 2.16 (s,3H), 2.20 (s, 3H), 2.22 (s, 3H), 2.24 (s, 3H), 2.50-2.60 (m,2H), 2.71-2.81 (m, 2H), 3.34 (s, i.5H), 3.44 (s, 0.5H), 5.77(d, 0.75H, J=3.OHz), 5.82 (d, 0.25H, J=2.9Hz), 5.90-5.95(m, 1H), 6.44 (d, 0.75H, J=8.3Hz), 6.49 (d, 0.25H, J=8.iHz),6.74 (d, 0.25H, J=7.8Hz), 6.78 (d, 0.75H, J=8.OHz), 6.85-6.93 (m, 2.75H), 7.11-7.13 (m, i.75H), 7.20 (s, 0.75H), 7.22(s, 0.25H), 7.41 (s, 0.25H), 7.51 (s, 0.25H), 8.68 (d, 0.75H,J=8.5Hz), 8.72 (d, 0.25H, J=8.OHz), 10.47 (s, 0.25H), 10.57(s, 0.75H); m/z: 565 [M+H]+ (calc. mass: 564).

Reference： [1]Patent: WO2018/138362,2018,A1 .Location in patent: Page/Page column 151; 164

82
C₁₉H₁₇NO₃ [ No CAS ]
[ 54593-26-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetrakis(dimethylsilyloxy)silane; iron(II) sulfate; In ethanol; at 80℃; for 24h;	In the air, a 25 mL reaction flask was sequentially charged with ferrous sulfate (0.05 mmol), alkene 1ad (0.5 mmol), and tetrakis(dimethylsiloxy)silane (2.0 mmol).Ethanol (2.0 mL). After mixing at room temperature,The reaction mixture is reacted at 80 C24h. At the end of the reaction, direct chromatography gave a yield of 87%.

Reference： [1]Patent: CN109796293,2019,A .Location in patent: Paragraph 0123-0125; 0151

83
[ 54593-26-9 ]
[ 765-30-0 ]
C₉H₁₂N₂O [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 2170 - 2178

84
[ 54593-26-9 ]
N3-cyclopropyl-N3-((3,5-dimethylisoxazol-4-yl)methyl)-N1,N1-dimethyl-1H-1,2,4-triazole-1,3-disulfonamide [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 2170 - 2178

85
[ 54593-26-9 ]
N-((3,5-dimethylisoxazol-4-yl)methyl)cyclopropylamine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 2170 - 2178

86
[ 54593-26-9 ]
C₂₀H₂₄ClN₃O₅S [ No CAS ]

Reference： [1]Patent: WO2019/171379,2019,A1

87
[ 54593-26-9 ]
C₂₂H₃₀N₄O₅S [ No CAS ]

Reference： [1]Patent: WO2019/171379,2019,A1

88
[ 41661-47-6 ]
[ 54593-26-9 ]
C₁₇H₁₉N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃;Inert atmosphere;	[000298] 4-Piperidinone (0.92 gr, 6 mmol) was placed in a 25 ml round bottom flask and cooled to 0 C. Boron trifluoride (10 mL) was added dropwise followed by the aldehyde (1.5 gr, 12 mmol) in one portion. The reaction mixture was stirred overnight at room temperature under nitrogen atmosphere. The reaction was carefully quenched with a saturated solution of NaHCC . The solid precipitated out from the solution was filtered under reduced pressure, washed with water and EtOH to give the intermediate El-1 (Scheme 7) as a yellow solid (1.2 gr, 3.8 mmol, 63%).

Reference： [1]Patent: WO2019/171379,2019,A1 .Location in patent: Paragraph 000298

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[ CAS No. 54593-26-9 ] {[proInfo.proName]}

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[ 54593-26-9 ] Synthesis Path-Upstream 1~7

[ 54593-26-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 54593-26-9 ]

Aldehydes

Related Parent Nucleus of [ 54593-26-9 ]

Isoxazoles

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[ 54593-26-9 ]

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[ 54593-26-9 ]