ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate -Drug Synthesis Database

【结构式】

【分子编号】51810

【品名】ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate

【CA登记号】

【分子式】C₁₂H₁₂F₂O₃

【分子量】242.2222864

【元素组成】C 59.5% H 4.99% F 15.69% O 19.82%

与该中间体有关的原料药合成路线共 7 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5 合成路线6 合成路线7

合成路线1

该中间体在本合成路线中的序号：(III)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with lmalonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)--3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with cyclopentyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

参考文献中间体

合成目标

【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	51809	2,6-Difluorophenylacetic acid	85068-28-6	C₈H₆F₂O₂	详情	详情
(II)	14338	potassium 3-ethoxy-3-oxopropanoate	6148-64-7	C₅H₇KO₄	详情	详情
(III)	51810	ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate		C₁₂H₁₂F₂O₃	详情	详情
(IV)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(V)	51811	6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone		C₁₁H₈F₂N₂OS	详情	详情
(VI)	51794	1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride	930-28-9	C₅H₉Cl	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with malonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with methyl chloride by means of K2CO3 to afford the target pyrimidinone.

参考文献中间体

合成目标

【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	51809	2,6-Difluorophenylacetic acid	85068-28-6	C₈H₆F₂O₂	详情	详情
(II)	14338	potassium 3-ethoxy-3-oxopropanoate	6148-64-7	C₅H₇KO₄	详情	详情
(III)	51810	ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate		C₁₂H₁₂F₂O₃	详情	详情
(IV)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(V)	51811	6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone		C₁₁H₈F₂N₂OS	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with malonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with isopropyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

参考文献中间体

合成目标

【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	51809	2,6-Difluorophenylacetic acid	85068-28-6	C₈H₆F₂O₂	详情	详情
(II)	14338	potassium 3-ethoxy-3-oxopropanoate	6148-64-7	C₅H₇KO₄	详情	详情
(III)	51810	ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate		C₁₂H₁₂F₂O₃	详情	详情
(IV)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(V)	51811	6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone		C₁₁H₈F₂N₂OS	详情	详情
(VI)	29984	2-chloropropane	75-29-6	C₃H₇Cl	详情	详情

合成路线4

该中间体在本合成路线中的序号：(III)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with malonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with butyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

参考文献中间体

合成目标

【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	51809	2,6-Difluorophenylacetic acid	85068-28-6	C₈H₆F₂O₂	详情	详情
(II)	14338	potassium 3-ethoxy-3-oxopropanoate	6148-64-7	C₅H₇KO₄	详情	详情
(III)	51810	ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate		C₁₂H₁₂F₂O₃	详情	详情
(IV)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(V)	51811	6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone		C₁₁H₈F₂N₂OS	详情	详情
(VI)	51818	n-Butyl chloride; Butyl chloride; N-Propylcarbinyl chloride; 1-Chlorobutane	109-69-3	C₄H₉Cl	详情	详情

合成路线5

该中间体在本合成路线中的序号：(III)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with malonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with isobutyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

参考文献中间体

合成目标

【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	51809	2,6-Difluorophenylacetic acid	85068-28-6	C₈H₆F₂O₂	详情	详情
(II)	14338	potassium 3-ethoxy-3-oxopropanoate	6148-64-7	C₅H₇KO₄	详情	详情
(III)	51810	ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate		C₁₂H₁₂F₂O₃	详情	详情
(IV)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(V)	51811	6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone		C₁₁H₈F₂N₂OS	详情	详情
(VI)	13624	1-Chloro-2-methylpropane; Isobutyl chloride	513-36-0	C₄H₉Cl	详情	详情

合成路线6

该中间体在本合成路线中的序号：(III)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with lmalonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with 1-ethylpropyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

参考文献中间体

合成目标

【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	51809	2,6-Difluorophenylacetic acid	85068-28-6	C₈H₆F₂O₂	详情	详情
(II)	14338	potassium 3-ethoxy-3-oxopropanoate	6148-64-7	C₅H₇KO₄	详情	详情
(III)	51810	ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate		C₁₂H₁₂F₂O₃	详情	详情
(IV)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(V)	51811	6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone		C₁₁H₈F₂N₂OS	详情	详情
(VI)	51797	1-methylpropyl chloride; 2-Chlorobutane; 1-Chloro-1-methylpropane; Sec-Butyl Chloride	78-86-4	C₄H₉Cl	详情	详情

合成路线7

该中间体在本合成路线中的序号：(III)

The condensation of 2-(2,6-difluorophenyl)acetic acid (I) with lmalonic acid monoethyl ester sodium salt (II) gives 4-(2,6-difluorophenyl)--3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) to yield 6-(2,6-difluorobenzyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is reacted with cyclohexyl chloride (VI) by means of K2CO3 to afford the target pyrimidinone.

参考文献中间体

合成目标

【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	51809	2,6-Difluorophenylacetic acid	85068-28-6	C₈H₆F₂O₂	详情	详情
(II)	14338	potassium 3-ethoxy-3-oxopropanoate	6148-64-7	C₅H₇KO₄	详情	详情
(III)	51810	ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate		C₁₂H₁₂F₂O₃	详情	详情
(IV)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(V)	51811	6-(2,6-difluorobenzyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone		C₁₁H₈F₂N₂OS	详情	详情
(VI)	51795	chlorocyclohexane; Hexahydrochlorobenzene; Cyclohexyl chloride	542-18-7	C₆H₁₁Cl	详情	详情

Extended Information