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 1642440ノート

反応式

HRID 1642440 の反応式
[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

参加物

5

反応物 3

HCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66753580HCID 66753580、化合物

生成物 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-one収率 46.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)+.

出典と根拠

ORDレコード
ord-1add290fb15b44cc9fbf201d445c9329
出典データセット
uspto-grants-2012_02
特許番号
US08119647B2

反応ノート

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