62254-74-4|5-Methylisoxazole-3-carboxaldehyde| Ambeed

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Quality Control of [ 62254-74-4 ] Purity: 95% SDS Specification

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Product Details of [ 62254-74-4 ]

CAS No. :	62254-74-4
Formula :	C₅H₅NO₂
M.W :	111.10
SMILES Code :	O=CC1=NOC(C)=C1
MDL No. :	MFCD06797459
InChI Key :	OCOCVXUEFWNRJU-UHFFFAOYSA-N
Pubchem ID :	2795222

Safety of [ 62254-74-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H228-H302
Precautionary Statements:	P210-P280
Class:	4.1
UN#:	1325
Packing Group:	Ⅲ

Application In Synthesis of [ 62254-74-4 ]

* 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.

Downstream synthetic route of [ 62254-74-4 ]

[ 62254-74-4 ] Synthesis Path-Downstream 1~41

1
[ 23429-22-3 ]
[ 62254-74-4 ]

References: [1]Gazzetta Chimica Italiana,1942,vol. 72,p. 99,106.

2
[ 35166-33-7 ]
[ 62254-74-4 ]

Yield	Reaction Conditions	Operation in experiment
39.71%	With manganese(IV) oxide; In dichloromethane; at 25℃; for 16h;	To a solution of (5-methylisoxazol-3-yl) methanol (10.0 g, 88.0 mmol, 1 eq.) in DCM (100 mL) was added MnO2 (38.4 g, 442 mmol, 5 eq.). The mixture was stirred at 25 C for 16 hours and filtrated. The filtrate was concentrated in vacuum to give 5- methylisoxazole-3-carbaldehyde (6.50 g, 35.0 mmol, 39.71 % yield) as yellow oil.1H NMR (400 MHz, CDCl3) δ = 10.12 (s, 1H), 6.40 (s, 1H) 2.53 (s, 3H).
39.71%	With manganese(IV) oxide; In dichloromethane; at 25℃; for 16h;	To a solution of (5-methylisoxazol-3-yl) methanol (10.0 g, 88.0 mmol, 1 eq.) in DCM (100 mL) was added MnO2 (38.4 g, 442 mmol, 5 eq.). The mixture was stirred at 25 C for 16 hours and filtrated. The filtrate was concentrated in vacuum to give 5- methylisoxazole-3-carbaldehyde (6.50 g, 35.0 mmol, 39.71 % yield) as yellow oil.1H NMR (400 MHz, CDCl3) δ = 10.12 (s, 1H), 6.40 (s, 1H) 2.53 (s, 3H).

References: [1]Patent: WO2019/238633,2019,A1 .Location in patent: Page/Page column 104.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 3168 - 3185.
[3]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.
[4]Patent: WO2022/11123,2022,A1 .Location in patent: Paragraph 0731; 0739; 0740.
[5]Patent: WO2022/11123,2022,A1 .Location in patent: Paragraph 0731; 0739; 0740.

3
[ 62254-74-4 ]
[ 141-82-2 ]
[ 71810-79-2 ]

References: [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 581 - 593.

4
[ 62254-74-4 ]
[ 7071-15-0 ]
[ 74531-30-9 ]

References: [1]Liebigs Annalen der Chemie,1980,p. 542 - 556.

5
[ 62254-74-4 ]
[ 4244-84-2 ]
[ 344332-58-7 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.

6
[ 62254-74-4 ]
[ 3633-17-8 ]
[ 344347-58-6 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.

7
5-N,N-Trimethylisoxazol-3-carbonsaeureamid [ No CAS ]
[ 62254-74-4 ]

References: [1]Liebigs Annalen der Chemie,1980,p. 542 - 556.

8
[ 62254-74-4 ]
[ 13633-26-6 ]
1-(5-methyl-isoxazol-3-yl)-2-phenyl-penta-2,4-dien-1-ol [ No CAS ]
1-(5-methyl-isoxazol-3-yl)-2-phenyl-penta-2,4-dien-1-ol [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 16448 - 16449.

9
[ 62254-74-4 ]
[ 145441-04-9 ]

References: [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 581 - 593.

10
[ 62254-74-4 ]
[ 83222-59-7 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.

11
[ 62254-74-4 ]
[ 83232-65-9 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.

12
[ 62254-74-4 ]
[ 83222-52-0 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.

13
[ 62254-74-4 ]
[ 83222-53-1 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.

14
[ 3209-72-1 ]
[ 62254-74-4 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.

15
[ 615-79-2 ]
[ 62254-74-4 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 557 - 560.

16
[ 62254-74-4 ]
[ 74531-39-8 ]

References: [1]Liebigs Annalen der Chemie,1980,p. 542 - 556.

17
[ 62254-74-4 ]
[ 113077-70-6 ]
[ 850646-74-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol; at 90℃; for 5h;Heating / reflux;	P--Toluenesulfonyl methyl isocyanide (1.75 gm, 8. 97 mmol) and Potassium carbonate (1.24 gm, 8.97 mmol) were added to a solution of 5-Methyl-isoxazole-3-carbaldehyde (1.0 gm, 8. 97 mmol) in 35 ml of dry methanol and the reaction mixture was refluxed (90C) for 5 hours. The reaction was cooled to room temperature and concentrated under reduce pressure. The residue was partitioned in diethyl ether (100 ml) and water (200 ml). The organic layer was separated and the aqueous extracted with diethyl ether. The organic extracts were washed with brine and water, dried over sodium sulfate and concentrated under reduced pressure to give the title compound as yellowish solid (1.25gm). LC/MS: 87%, 238 (M+1)

References: [1]Patent: WO2005/40142,2005,A1 .Location in patent: Page/Page column 39.

18
[ 19788-35-3 ]
[ 62254-74-4 ]

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 5.5h;	Diisobutylaluminumhydride (1. OM in DCM, 25. 5ni, 25.5 mmol) was added drop wise over 20 minutes to a solution of methyl-5-methylisoxazole-3-carboxylate (3.0 gm, 21.3 mmol) in 35 ml of dry methylene chloride, with stirring at-78C, and the reaction mixture was stirred at-78C for 5.5 hours. The reaction was warmed to-40C and quenched with ice (60 gm). After the biphasic mixture was allowed to warm to room temperature, potassium sodium tartrate tetrahydrate (100 ml saturated aqueous solution) was added. The bilayer were separated, the aqueous was extracted with methylene chloride. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure to give 5-Methyl-isoxazole-3-carbaldehyde as white solid (1.3 gm).
		In anhydrous THF (40 ml), 5-methylisoxazole-3-carboxylic acid methyl ester (Avogato Co., Ltd.) (2.00 g) was dissolved. In an ice bath, a solution (20 ml) of lithium aluminum hydride (0.67 g) in anhydrous THF was dropped in the solution over 15 minutes. After 10 minutes, the mixture was taken from the ice bath and then stirred at room temperature for 1 hour. After completion of the reaction, the resultant solution was added with anhydrous sodium sulfate and then added with a 20% sodium hydroxide aqueous solution (15 ml). The solution was filtrated through Celite and the solvent was distilled off. The residue was dissolved in chloroform (85 ml) and added with manganese dioxide (chemically processed product) (17.0 g), followed by stirring for 4.5 hours. After completion of the reaction, the solution was filtrated through Celite and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (164 mg) as a white solid. MS(EI,Pos.):m/z=111[M]+ 1H-NMR(500MHz,CDCl3):δ=2.53(3H,s),6.39(1H,s),10.12(1H,s).

References: [1]Patent: WO2005/40142,2005,A1 .Location in patent: Page/Page column 38-39.
[2]Patent: EP1550657,2005,A1 .Location in patent: Page/Page column 81.
[3]Patent: WO2019/238633,2019,A1 .

19
[ 62254-74-4 ]
[ 675137-32-3 ]
[ 675135-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid; In methanol; at 20℃; for 17.0833h;pH 5;	The compound (110 mg) obtained in Example 47-3 and the compound (58.0 mg) obtained in Example 85-1 were dissolved in anhydrous methanol (5.0 ml). The solution was added with sodium cyanoborohydride (39.4 mg) and then added with acetic acid (1.0 ml) to adjust the solution to pH 5, followed by stirring for 5 minute and then stirring at room temperature for 17 hours. After completion of the reaction, methanol was distilled off and a 1 mol/l sodium hydroxide aqueous solution was added to adjust the solution to pH 11, followed by extraction with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous magnesium sulfate, followed by distilling the solvent off. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol), added with methanol and 1 mol/l hydrochloric acid, and distilled off, thereby obtaining the subject compound (21.3 mg) as a white crystal. MS(FAB,Pos.):m/z=515[M+H]+ 1H-NMR(500MHz,DMSO-d6+D2O):δ=0.82(6H,t,J=7.3Hz),1.43(4H,sext.,J=7.3Hz),2.32 (4H,t,J=7.5Hz),2.40(3H,s),3.48(2H,s),3.59(2H,s),3.67(2H,s),3.70(2 H,s),6.34(1H,s),6.87(1H,s),7.12(1H,s),7.27(2H,d,J=8.5Hz),7.5 4(2H,d,J=8.3Hz),7.68(2H,J=8.5Hz),7.89(2H,d,J=8.1Hz).

References: [1]Patent: EP1550657,2005,A1 .Location in patent: Page/Page column 81.

20
[ 62254-74-4 ]
[ 638-07-3 ]
2-(5-Methylisoxazol-3-ylidene)-3-oxo-4-chlorobutyric acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 69 2-(5-Methylisoxazol-3-ylidene)-3-oxo-4-chlorobutyric acid ethyl ester STR92 79.5 g of 5-methylisoxazole-3-aldehyde were reacted with 4-chloroacetoacetic acid ethyl ester as described in Example 24. A crude product, which was chromatographically pure, was obtained. This isomer ratio was 2:1. IR (film): 2950, 1720, 1590, 1420, 1255, 1225, 1020 cm-1. NMR (CDCl3): δ=7.64/7.61 [1] s, 6.21/6.08 [1] s, 4.47 [2] s, 4.40/4.32 [2] q, J=7 Hz, 2.43 [3] s, 1.32 [3] t, J=7 Hz ppm.

References: [1]Patent: US4416880,1983,A .

21
[ 62254-74-4 ]
[ 62254-75-5 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 26 STR175 14.0 pts. by wt. of 5-methyl-3-formyl-isoxazole are reacted with 25.6 pts. by wt. of 1-amino-2-oxo-imidazolidine hydrochloride in 100 pts. by vol. of water as in Example 25.1. After 90 minutes, the precipitate is filtered off, washed with water, dried and recrystallized from absolute acetonitrile. 12.5 pts. by wt. of 1-(5-methyl-isoxazol-3-yl-methyleneamino)-2-oxo-imidazolidine of melting point 195-7 C. are obtained. IR (paraffin oil): 3,220, 1,695 and 1,610 cm-1. NMR (CD3 OD): 7.65(s,1H), 7.47(s,broad,1H), 6.53(s,1H), 3.7(m,4H), 2.50(s,3H)δ. calculated: C 49.48; H 5.19; N 28.85; found: C 49.6; H 5.2; N 29.2. STR176 12.0 pts. by wt. of 1-(5-methyl-isoxazol-3-yl-methyleneamino)-2-oxo-imidazolidine, 21.0 pts. by wt. of triethylamine, 20.8 pts. by wt. of chlorotrimethylsilane and 12.3 pts. by wt.

References: [1]Patent: US4147693,1979,A .

22
[ 62254-74-4 ]
[ 868541-95-1 ]
[ 932400-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 40℃; for 2h;	To a solution of 2-amino-3-(1 ,3-thiazol-4-yl)propanoic acid, te/f-butyl ester (prepared in a similar manner to that described in Intermediate 3; 3.718 g) in dichloromethane (20 mL) was added a solution of <strong>[62254-74-4]5-methylisoxazole-3-carboxaldehyde</strong> (2.716 g) in dichloro- methane (35 mL). The mixture was heated at 40C for 2 hours, cooled to 200C and concentrated in vacuo to give the title compound as an oil.1H NMR (CDCI3): δ 8.75 (d, 1 H), 8.11 (s, 1 H), 7.01 (d, 1 H), 6.45 (s, 1 H), 4.44 (dd, 1 H), 3.57 (dd, 1 H), 3.30 (dd, 1 H), 2.44 (s, 3H) and 1.45 (s, 9H).
	In dichloromethane; at 40℃; for 2h;	To a solution of 2-amino-3-(1 ,3-thiazol-4-yl)propanoic acid, te/f-butyl ester (prepared in a similar manner to that described in Intermediate 3; 3.718 g) in dichloromethane (20 mL) was added a solution of <strong>[62254-74-4]5-methylisoxazole-3-carboxaldehyde</strong> (2.716 g) in dichloromethane (35 mL). The mixture was heated at 400C for 2 hours, cooled to 200C and concentrated in vacuo to give the title compound as an oil. 1H NMR (CDCI3): δ 8.75 (d, 1 H), 8.11 (s, 1 H), 7.01 (d, 1 H), 6.45 (s, 1 H), 4.44 (dd, 1 H), 3.57 (dd, 1 H), 3.30 (dd, 1 H), 2.44 (s, 3H) and 1.45 (s, 9H).

References: [1]Patent: WO2007/39144,2007,A1 .Location in patent: Page/Page column 21.
[2]Patent: WO2007/39145,2007,A1 .Location in patent: Page/Page column 20.

23
[ 62254-74-4 ]
[ 4276-09-9 ]
C₁₀H₁₆N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1318 - 1322.

24
[ 62254-74-4 ]
[ 1099-45-2 ]
[ 1065478-58-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7388 - 7398.

25
[ 62254-74-4 ]
[ 15174-69-3 ]
[ 1076188-34-5 ]

Yield	Reaction Conditions	Operation in experiment
		00267) To a mixture of commercially available 4'-hydroxy-3'-methylacetophenone (700 mg, 4.66 mmol) and NaOH (365 mg, 9.1 mmol) in 10 mL of absolute EtOH was added commercially available 5-methylisoxazole-3-carbaldehyde (518 mg, 4.66 mmol). The reaction mixture was stirred at room temperature for 18 hr. 5 mL of water was added and the reaction mixture was acidified with concentrated HCI to pH 5-6. The precipitate was filtered, washed15 <n="117"/>with water and dried to give (E)-l-(4-hydroxy-3-methylphenyl)-3-(5-methylisoxazol-3- yl)prop-2-en-l-one. MS (EI) for Ci4H13NO3: 244 (MH+).

References: [1]Patent: WO2008/133955,2008,A1 .Location in patent: Page/Page column 115-116.

26
[ 62254-74-4 ]
[ 89322-78-1 ]
C₅H₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydroxylamine hydrochloride; In dichloromethane; at 20℃; for 12h;	To a solution of S-methyl-3-isoxazolecarboxaldehyde (1.00 g, 9.00 mmol) in DCM (5 mL) was added subsequently pyridine (0.73 mL, 9.00 mmol) and hydroxylamine hydrochloride (0.63g, 9.00 mmol). After being stirred at room temperature for 12 h, the reaction mixture was diluted with methylene chloride (50 mL) and extracted with water (2 x 50 mL). The organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to provide a white solid. The crude product, obtained as a mixture of syn- and αn'-oximes, was used in the next reaction without further purification.

References: [1]Patent: WO2009/70485,2009,A1 .Location in patent: Page/Page column 135.

27
[ 62254-74-4 ]
[ 180-44-9 ]
[ 1162762-61-9 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 8066 - 8076.

28
[ 62254-74-4 ]
[ 623-00-7 ]
[ 1188281-46-0 ]

References: [1]European Journal of Organic Chemistry,2009,p. 4041 - 4050.

29
[ 62254-74-4 ]
[ 868541-95-1 ]
[ 922-67-8 ]
rel-(2S,5R)-5-(5-methylisoxazol-3-yl)-2-(1,3-thiazol-4-ylmethyl)-2,5-dihydro-1H-pyrrole-2,4-dicarboxylic acid, 2-tert-butyl ester, 4-methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 14; rel-(2S,5R)-5-(5-Mefihyl isoxazol-3-yl)-2-(1,3-th iazol-4-yl methyl)-2,5-d i hydro-1 H- pyrrole-2,4-dicarboxylic acid, 2-tert-butyl ester, 4-methyl ester; A mixture of Intermediate 13 (0.96 g, 4.20 mmol) and 5-methylisoxazol-3-carboxaldehyde (0.93 g, 8.37 mmol) in dichloromethane (15 mL) was heated at 40C for 3h, allowed to cool to room temperature and left to stand overnight. The reaction mixture was evaporated under reduced pressure, to give a mixture of 2-[[N-(5-methylisoxazol-3- yl)methylene]amino]-3-(1,3-thiazol-4-yl)propanoic acid, tert-butyl ester and intermediate 13 (3: 1 ratio). This mixture was dissolved in dry THF (15 mL), lithium bromide (0.355 g, 4.09 mmol) was added and the mixture stirred under nitrogen at 0C. Triethylamine (0.57 mL, 4.09 mmol) was added followed by methyl propiolate (0.3 mL, 3.37 mmol) and the resulting mixture was stirred at 0C for 20 min and allowed to warm to room temperature. After 2 hours, saturated ammonium chloride solution (40 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel using ethyl acetate-cyclohexane (1: 2 v/v) as eluent to give the title compound as an oil which solidified on standing. MS calcd for (C19H23N3O5S + H) +: 406. MS found (electrospray) : (M+H) (at) = 406

References: [1]Patent: WO2005/103045,2005,A1 .Location in patent: Page/Page column 24-25.

30
[ 62254-74-4 ]
[ 1083049-06-2 ]
C₂₀H₂₆N₆O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7946 - 7949.

31
[ 62254-74-4 ]
[ 1052094-42-4 ]
[ 1062093-78-0 ]

References: [1]ChemBioChem,2010,vol. 11,p. 1224-1227+1158.

32
[ 62254-74-4 ]
[ 1293396-31-2 ]
[ 1293396-04-9 ]

Yield	Reaction Conditions	Operation in experiment
		Method A: Reductive amination, exemplified by synthesis of 4-{4-(4-fluorophenyl)-1-[(1-substituted)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidines (Example 29) A solution of 4-[4-(4-fluorophenyl)-1-piperidin-4-yl-1H-imidazol-5-yl]pyrimidine (C15) (0.068 mmol) in dichloroethane (1 mL) was added to a vial containing the appropriate aldehyde (0.075 mmol), and the mixture was treated with triethylamine (0.15 mmol) and acetic acid (0.38 mmol). The vial was shaken for 30 minutes, at which time sodium triacetoxyborohydride (0.22 mmol) was added and shaking was continued for an additional 66 hours. The reaction was quenched with aqueous sodium hydroxide solution (1 N, 2 mL), added to dichloroethane (2 mL) and shaken. The organic layer was separated and filtered through an empty solid-phase extraction cartridge, and the filtrate was concentrated in vacuo. The residue was dissolved in dimethyl sulfoxide (1 mL) and purified by reversed-phase HPLC (Column: Waters XBridge C18, 5 μm; Mobile phase A: 0.03% NH4OH in water (v/v); Mobile phase B: 0.03% NH4OH in acetonitrile (v/v); Gradient: 15% to 95% B).

References: [1]Patent: US2011/98272,2011,A1 .Location in patent: Page/Page column 30; 33.

33
[ 62254-74-4 ]
[ 1219004-56-4 ]
[ 1219004-82-6 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of 19 (300 mg, 0.70 mmol) in tetrahydrofuran (3 mL) was slowly added to a solution of lithium diisopropylamide (LDA) in heptane/tetrahydrofuran/ethylbenzene (2 M, 0.38 mL, 0.76 mmol) at 78oC, and the resultant solution was stirred at -78oC for 30 minutes. Chlorotitanium triisopropoxide (1 M, 2.8 mL) was then added slowly, and the resulting mixture was stirred at 40oC for 1 hour. The reaction was cooled to -78oC, and propionaldehyde (49 mg, 0.84 mmol) was added slowly. This mixture was then warmed to 40oC, and stirred at 40oC for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (1 mL), diluted with 10 mL of tetrahydrofuran, and treated with Celite for 1 hour. The resultant slurry was filtered and concentrated. The resultant residue was purified by silica gel chromatography (gradient: 95:5 hexanes:ethyl acetate to 65:35 hexanes:ethyl acetate) to provide 20 as a white solid. Yield: 230 mg, 68%.

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2536 - 2543.

34
[ 62254-74-4 ]
[ 1400639-13-5 ]
[ 1400639-30-6 ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: Phenanthropiperidine 6 (1.00 equiv, 0.05-0.08 mmol) and aldehyde (3.00 equiv) were dissolved in anhydrous DCE (0.02 M) and allowed to stir for 5 min at rt. Na(OAc)3BH (5.00 equiv) was added in one portion (as a solid) and the reaction was allowed to stir at room temperature until completion (6-24 h, monitored via TLC). The reaction was quenched with 10% NaOH and extracted with CH2Cl2 (3×). The combined organic layers were dried over anhydrous MgSO4, concentrated, and purified via prep TLC (2.5-5% MeOH (2.0 M NH3 in MeOH)/CH2Cl2).

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5893 - 5900.

35
[ 62254-74-4 ]
[ 942949-34-0 ]
[ 1402709-79-8 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 8721 - 8734,14.

36
[ 62254-74-4 ]
[ 536-90-3 ]
[ 1428972-20-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 60℃; for 6h;Sealed tube;	General procedure: A mixture of an aldehyde (1.0 eq) and an amine (1.0 eq) was heated in a sealed tube at 60 C for 6 h. The crude material was dried under vacuum over phosphorus(V) oxide to give quantitatively the imine which was used in the next step without further purification.

References: [1]Patent: WO2013/45516,2013,A1 .Location in patent: Page/Page column 130; 141.
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 8390 - 8401.

37
[ 62254-74-4 ]
[ 1428969-01-0 ]

References: [1]Patent: WO2013/45516,2013,A1 .

38
[ 62254-74-4 ]
[ 1428969-02-1 ]

References: [1]Patent: WO2013/45516,2013,A1 .

39
[ 62254-74-4 ]
[ 1428968-12-0 ]

References: [1]Patent: WO2013/45516,2013,A1 .
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 8390 - 8401.

40
[ 62254-74-4 ]
[ 20265-39-8 ]
[ 1428972-63-7 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium sulfate; In ethanol; at 80℃;	General procedure: To a mixture of an aldehyde (1.0 eq) and magnesium sulfate (1.3 eq) in ethanol was added an amine (1.0 eq). The mixture was heated overnight at 80 C and filtered. The filtrate was concentrated under reduced pressure to give quantitatively the imine which was used without further purification in the next step.

References: [1]Patent: WO2013/45516,2013,A1 .Location in patent: Page/Page column 130; 173.

41
[ 62254-74-4 ]
(+/-)-α-methylserine methyl ester hydrochloride [ No CAS ]
C₁₀H₁₄N₂O₄ [ No CAS ]

References: [1]Chemical Biology and Drug Design,2013,vol. 81,p. 645 - 649.

Historical Records

Technical Information

• Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 62254-74-4 ]

Aldehydes

A117227 [54593-26-9]

3,5-Dimethyl-4-isoxazolecarbaldehyde

Similarity: 0.75

A110131 [16401-14-2]

Isoxazole-5-carbaldehyde

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A104829 [220780-57-4]

3-Bromoisoxazole-5-carbaldehyde

Similarity: 0.58

Related Parent Nucleus of
[ 62254-74-4 ]

Isoxazoles

A247872 [24068-54-0]

1-(5-Methylisoxazol-3-yl)ethanone

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A113298 [300-87-8]

3,5-Dimethylisoxazole

Similarity: 0.87

A104403 [3445-52-1]

5-Methylisoxazole-3-carboxamide

Similarity: 0.87

A104932 [3405-77-4]

5-Methylisoxazole-3-carboxylic acid

Similarity: 0.85

A311062 [1050590-34-5]

(5-Methylisoxazol-3-yl)methanamine hydrochloride

Similarity: 0.80

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CAS No.: 62254-74-4

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