Sodium ethoxide → 7-[(E)-2-(2-Cyclopropylmethoxy-3-methoxyphenyl)-1-ethenyl]-6-(4-(2,2,2-tri fluoroethoxy)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642440노트

반응식

HRID 1642440 반응식
[CH3:1][C:2]1[N:3]=[C:4]2[S:23][CH:22]=[CH:21][N:5]2[C:6](=[O:20])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:10][CH:9]=1.[CH:24]1([CH2:27][O:28][C:29]2[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]=O)[CH2:26][CH2:25]1.[O-]CC.[Na+]>C(O)C>[CH:24]1([CH2:27][O:28][C:29]2[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:30]=2/[CH:31]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:23][CH:22]=[CH:21][N:5]3[C:6](=[O:20])[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([F:18])([F:19])[F:17])=[CH:10][CH:9]=2)[CH2:25][CH2:26]1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66753580HCID 66753580, 화합물

생성물 1

HCID 444674607-[(E)-2-(2-Cyclopropylmethoxy-3-methoxyphenyl)-1-ethenyl]-6-(4-(2,2,2-tri fluoroethoxy)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one수율 46.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The title compound was synthesized by condensation of Intermediate 11 (325 mg, 0.95 mmol) with 2-cyclopropylmethoxy-3-methoxybenzaldehyde (255 mg, 1.20 mmol) in presence of sodium ethoxide (129 mg, 1.90 mmol) in ethanol (25 ml) according to the procedure of Example 24 to give 235 mg of the desired product; 1H NMR (300 MHz, DMSO-d6) δ 0.27 (br s, 2H), 0.51 (br s, 2H), 1.04-1.06 (m, 1H), 3.68-3.70 (m, 2H), 3.77 (m, 3H), 4.81-4.83 (m, 2H), 6.89-6.98 (m, 4H), 7.13-7.15 (m, 2H), 7.27-7.29 (m, 2H), 7.49 (br s, 1H), 7.98 (br s, 1H), 8.14 (d, J=16.2 Hz, 1H); ESI-MS (m/z) 529.23 (M+H)+.

출처 및 근거

ORD 기록
ord-1add290fb15b44cc9fbf201d445c9329
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119647B2

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