4,5-Dimethylthiazole → HCID 57754582、化合物

HRID 227049

反応式

HRID 227049 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH3:7].[Li]CCCC.[Br-].[Mg+2].[Br-].CON(C)[C:19]([C:21]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Br:39])[N:34]=2)[CH:22]=1)=[O:20]>C1COCC1.S1C=CN=C1>[Br:39][C:35]1[N:34]=[C:33]([CH2:32][N:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30](=[O:31])[C:21]([C:19]([C:4]3[S:5][C:6]([CH3:7])=[C:2]([CH3:1])[N:3]=3)=[O:20])=[CH:22]2)[CH:38]=[CH:37][CH:36]=1

参加物

7

反応物 4

HCID 625104,5-DimethylthiazoleHCID 82241Magnesium BromideHCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 178418339Butyllithium

生成物 1

HCID 57754582HCID 57754582、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 9256Thiazole溶媒

反応条件

温度
-78 °C

実験手順

585 mg (5.17 mmol) of 4,5-dimethylthiazole was dissolved in 10 mL of anhydrous THF and cooled down to −78° C. 2.07 mL of 2.5 M BuLi in hexanes was added dropwise, followed after 15 minutes by 1.0 g of anhydrous magnesium bromide. The solution was warmed up to rt. The final compound was prepared from 120 mg (0.30 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 2 mL THF and 1.64 mL of the thiazole salt solution. Yield: 13 mg of a white solid. LC-MSD, m/z for C21H16BrN3O2S [M+H]+=454.0, 456.0; HPLC retention time: 2.2 min.

後処理

  1. temperatureThe solution was warmed up to rt

出典と根拠

ORDレコード
ord-059639348c8b42119398978851e28049
出典データセット
uspto-grants-2009_07
特許番号
US07557213B2

関連ノート

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