92901-94-5|(2,5-Dimethyloxazol-4-yl)methanol| Ambeed

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Quality Control of [ 92901-94-5 ] Purity: 95% SDS Specification

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Product Details of [ 92901-94-5 ]

CAS No. :	92901-94-5
Formula :	C₆H₉NO₂
M.W :	127.14
SMILES Code :	OCC1=C(C)OC(C)=N1
MDL No. :	MFCD07772804
InChI Key :	YURZVIJMKNBRIC-UHFFFAOYSA-N
Pubchem ID :	7162083

Safety of [ 92901-94-5 ]

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

Application In Synthesis of [ 92901-94-5 ]

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

Downstream synthetic route of [ 92901-94-5 ]

[ 92901-94-5 ] Synthesis Path-Downstream 1~33

1
[ 23000-14-8 ]
[ 92901-94-5 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 5003 - 5006.

2
[ 92901-94-5 ]
[ 92901-88-7 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 5003 - 5006.

3
[ 23000-15-9 ]
[ 92901-94-5 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5310 - 5311.

4
[ 32315-10-9 ]
[ 3830-10-2 ]
[ 92901-94-5 ]
[ 903576-24-9 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5310 - 5311.

5
[ 92901-94-5 ]
[ 940879-46-9 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2399 - 2407.

6
[ 141567-53-5 ]
[ 333-27-7 ]
2-ethyl-4-(hydroxymethyl)oxazole [ No CAS ]
[ 92901-94-5 ]

References: [1]Organic Letters,1999,vol. 1,p. 87 - 90.
[2]Organic Letters,1999,vol. 1,p. 87 - 90.

7
[ 92901-94-5 ]
[ 859850-62-7 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2399 - 2407.

8
[ 92901-94-5 ]
[ 1026044-87-0 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2399 - 2407.

9
[ 92901-94-5 ]
[ 940879-52-7 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2399 - 2407.

10
[ 92901-94-5 ]
[ 1026742-99-3 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2399 - 2407.

11
[ 92901-94-5 ]
C₃₄H₅₄N₆O₈S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2399 - 2407.

12
[ 5431-93-6 ]
[ 92901-94-5 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1.6Dimethyloxazolyl Methanol; Sodium nitrite (12.2 g, 0.18 mol) in water was added dropwise to a solution of ethyl acetoacetate (19.5 mL, 0.15 mol) in glacial acetic acid at r.t. for 1 h. The resulting mixture was stirred for further 1 h at r.t, 80 mL of water added, and stirring continued for 2 h. The reaction mixture was extracted with ether for three times, washed with aqueous Na HCO3, water and brine. The organic layer was dried, concentrated to afford the crude product. Without further purification, the crude product (6.5 g, 40.8 mmol) in a mixture of acetic anhydrous (19.3 mL, 0.21 mol), acetic acid (58 mL), and 210 mg of Pd/C (10% w/w) was hydrogenated at 50 Psi pressure for 1.5 h. The catalyst and solvent were removed and the residue was triturated with hexanes to give ethyl N-acetylacetoacetate as solid, m.p. 38-40 C.The above solid product (3.3 g, 17.6 mmol) was treated with thionyl chloride (1.3 mL, 17.6 mmol) in dry benzene at r.t. The mixture was warmed to 30 C. for 1 h, and for 30 min under water-pump vacuum. The residue was diluted with EtOAc and washed with aqueous NaHCO3, water, and brine. The organic layer was dried, concentrated to give the crude product as a brown oil, which was further reduced by LAH to provide the desired alcohol as a light yellow solid. 1H-NMR: (300 MHz, CDCl3), δ: 4.51 (s, 2H); 2.58 (s, 3H); 2.43 (s, 3H), 2.31 (s, 3H).
		The above solid product (3.3 g, 17.6 mmol) was treated with thionyl chloride (1.3 mL, 17.6 mmol) in dry benzene at r.t. The mixture was warmed to 30 0C for 1 h, and for 30 min under water-pump vacuum. The residue was diluted with EtOAc and washed with aqueous NaHCO3, water, and brine. The organic layer was dried, concentrated to give the crude product as a brown oil, which was further reduced by LAH to provide the desired alcohol as a light yellow solid. 1H-NMR: (300 MHz, CDCl3), δ: 4.51 (s, 2 H); 2.58 (s, 3 H); 2.43 (s, 3 H), 2.31 (s, 3 H).

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5310 - 5311.
[2]Patent: US2008/125467,2008,A1 .Location in patent: Page/Page column 20.
[3]Patent: WO2006/34277,2006,A1 .Location in patent: Page/Page column 62.

13
[ 92901-94-5 ]
[ 887606-08-8 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5310 - 5311.

14
[ 92901-94-5 ]
[ 1008795-53-6 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5310 - 5311.

15
[ 92901-94-5 ]
{(R)-1-[(1S,2S,4R)-2-Hydroxy-1-isobutyl-4-((S)-1-isobutylcarbamoyl-2-methyl-propylcarbamoyl)-pentylcarbamoyl]-2-methanesulfonyl-ethyl}-carbamic acid 2,5-dimethyl-oxazol-4-ylmethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5310 - 5311.

16
[ 92901-94-5 ]
[ 92901-92-3 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 5003 - 5006.
[2]Journal of Organic Chemistry,1984,vol. 49,p. 5003 - 5006.

17
[ 92901-94-5 ]
[ 92901-91-2 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 5003 - 5006.

18
[ 92901-94-5 ]
[ 92901-90-1 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 5003 - 5006.

19
[ 92901-94-5 ]
[ 92901-89-8 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 5003 - 5006.

20
[ 92901-94-5 ]
[ 92901-84-3 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 5003 - 5006.

21
[ 342023-61-4 ]
[ 92901-94-5 ]
methyl 3-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20℃; for 8h;	Diethyl azodicarboxylate (40% in toluene, 1.00 g) was added dropwise slowly to a mixture of methyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate (500 mg), (2,5-dimethyl-4-oxazolyl]methanol (275 mg), triphenylphosphine (585 mg) and tetrahydrofuran (10 ml) at room temperature. After the mixture was stirred at room temperature for 8 hours, the reaction solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography, and methyl 3-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]3-phenyl-1H-pyrazol-4-yl]propionate (288 mg, yield: 44%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (6:5, volume ratio). NMR(CDCl3) δ : 2.31(3H, s), 2.41(3H, s), 2.49-2.58(2H, m), 2.90-2.99(2H, m), 3.62(3H, s), 4.86(2H, s), 5.24(2H, s), 6.97(2H, d, J=8.8 Hz), 7.18-7.47(6H, m), 7.59-7.66(2H, m).

References: [1]Patent: EP1228067,2004,B1 .Location in patent: Page 88-89.

22
[ 92901-94-5 ]
[ 141567-52-4 ]

Yield	Reaction Conditions	Operation in experiment
26.4 parts (100%)	With thionyl chloride; In chloroform;	EXAMPLE 7 To a solution of 18.5 parts of 2,5-dimethyl-4-oxazolemethanol in 200 parts of trichloromethane there were added dropwise 21.1 parts of thionyl chloride. After stirring for 2 hours at room temperature, the reaction mixture was evaporated and the residue was co-evaporated with methylbenzene, yielding 26.4 parts (100%) of 4-(chloromethyl)-2,5-dimethyloxazole hydrochloride (interm. 26).

References: [1]Patent: US5217980,1993,A .

23
[ 92901-94-5 ]
[ 124-63-0 ]
methanesulfonic acid 2,5-dimethyl-oxazol-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 187 1'-({6-Chloro-1-[(2,5-dimethyl-1,3-oxazol-4-yl)methyl]-1H-indol-3-yl}carbonyl)-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one Following the general procedure III as described above, the alkylation of 1'-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one (prepared according to example 19 above) with methanesulfonic acid 2,5-dimethyl-oxazol-4-ylmethyl ester (prepared by mesylation of (2,5-dimethyl-oxazol-4-yl)-methanol, described in Organic Letters (1999), 1(1), 87-90) gave the title compound.; Example 242 1'-({6-Chloro-1-[(2,5-dimethyl-1,3-oxazol-4-yl)methyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine Following the general procedure III as described above, the alkylation of 1'-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4'-piperidine] (prepared according to example 69) with methanesulfonic acid 2,5-dimethyl-oxazol-4-ylmethyl ester (prepared by mesylation of (2,5-dimethyl-oxazol-4-yl)-methanol, described in Organic Letters 1999, 1(1), 87-90) gave the title compound. ES-MS m/e (%): 476.2(M+H+).

References: [1]Patent: US2007/27173,2007,A1 .Location in patent: Page/Page column 87-88; 102.

24
tert-butyl 4-(4-(3,5-dichloro-4-hydroxyphenyl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]
[ 92901-94-5 ]
C₂₆H₃₀Cl₂N₄O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9790 - 9806.

25
[ 98432-01-0 ]
[ 92901-94-5 ]