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【结 构 式】

【分子编号】31897

【品名】5-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-oxoethyl]-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one

【CA登记号】

【 分 子 式 】C21H19FN2O3S

【 分 子 量 】398.4579432

【元素组成】C 63.3% H 4.81% F 4.77% N 7.03% O 12.05% S 8.05%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

This compound has been obtained by several related ways: 1.- The Sam and Thompson cyclization of 3-(2-thienyl)acrylic acid (I) gives the thienocyclopentanone (II), which is condensed with oxoacetic acid (III) yielding 2-(4-oxo-5,6-dihydro-4H-cyclopenteno[b]furan-5-ylidene)acetic acid (IV). The reduction of (IV) with Zn and acetic acid affords the corresponding saturated compound (V), which is condensed with 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (VI) by means of DCC and HOBt in dichloromethane to give the corresponding piperidide (VII). The protection of the ketonic group of (VII) with ethylene glycol and TsOH yields the ethylene ketal (VIII), which is reduced at the piperidide group with LiAlH4 in ethyl ether yielding the final intermediate (IX). Finally, this compound is treated with HCl to eliminate the ethylene ketal protecting group. 2.- The condensation of the thienocyclopentanone (II) with ethyl bromoacetate (X) by means of LDA gives the acetate (XI), which is hydrolyzed with KOH in ethanol affording the previously reported saturated acetic acid derivative (V). 3.- The condensation of acetate (XI) with piperidine (VI) by means of Me3Al gives also the previously reported piperidide (VII).

1 Negreira, J.; Cid, J.; Raviña, E.; et al.; Conformationally constrained butyrophenones with mixed dopaminergic (D(2)) and serotoninergic (5-HT(2A), 5-HT(2C)) affinities: Synthesis, pharmacology, 3D-QSAR, and molecular modeling of (aminoalkyl)benzo- and -thienocycloalkanones as putative atypical an. J Med Chem 1999, 42, 15, 2774.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(I) 31893 (Z)-3-(2-thienyl)-2-propenoic acid 15690-25-2 C7H6O2S 详情 详情
(II) 31894 5,6-dihydro-4H-cyclopenta[b]thiophen-4-one C7H6OS 详情 详情
(III) 15618 2-Oxoacetic acid; Glyoxylic Acid 298-12-4 C2H2O3 详情 详情
(IV) 31895 2-(4-oxo-4,6-dihydro-5H-cyclopenta[b]thiophen-5-ylidene)acetic acid C9H6O3S 详情 详情
(V) 31896 2-(4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophen-5-yl)acetic acid C9H8O3S 详情 详情
(VI) 17910 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole C12H13FN2O 详情 详情
(VII) 31897 5-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-oxoethyl]-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one C21H19FN2O3S 详情 详情
(VIII) 31898 3-[4,4-(Ethylenedioxy)-5,6-dihydro-4H-cyclopeta[b]thiophen-5-yl]-1-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)-1-propanone C23H23FN2O4S 详情 详情
(IX) 31899 1-[2-[4,4-(Ethylenedioxy)-5,6-dihydro-4H-cyclopenta[b]thiophen-5-yl]ethyl]-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine C23H25FN2O3S 详情 详情
(X) 16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
(XI) 31900 ethyl 2-(4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophen-5-yl)acetate C11H12O3S 详情 详情
Extended Information