Acetyl chloride → (2S,4S)-4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-N-(hex-5-enyl)-N-methylpyrrolidine-2-carboxamide hydrochloride

HRID 420092ノート

反応式

HRID 420092 の反応式
[Cl:1][C:2]1[C:3]([O:43][CH3:44])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][N:24](C(OC(C)(C)C)=O)[C@H:23]([C:33](=[O:42])[N:34]([CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:35])[CH2:22]1.C(Cl)(=O)C>CO>[ClH:1].[Cl:1][C:2]1[C:3]([O:43][CH3:44])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][NH:24][C@H:23]([C:33]([N:34]([CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:35])=[O:42])[CH2:22]1

参加物

4

反応物 2

HCID 6367Acetyl chlorideHCID 66650750(2S,4S)-tert-butyl 4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-2-(hex-5-enyl(methyl)carbamoyl)pyrrolidine-1-carboxylate2 回

生成物 1

HCID 66650405(2S,4S)-4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-N-(hex-5-enyl)-N-methylpyrrolidine-2-carboxamide hydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
40 °C

実験手順

Compound 134 (20.37 g) was suspended in anhydrous methanol (120 mL) under argon at room temperature. Separately acetyl chloride (3 eq.) was added to anhydrous methanol (70 mL) at 10-20° C. This solution was added to the compound 134 solution at 5° C. The reaction mixture was heated at 40° C. for 3-4 hrs. After the completion of the reaction, the reaction mixture was concentrated under vacuum and then co-evaporated with 100 mL of anhydrous dichloromethane. The product was then dried in a vacuum oven at 40-45° C. Compound 135 (19.81 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC).

後処理

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. customThe product was then dried in a vacuum oven at 40-45° C
  4. customCompound 135 (19.81 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC)

出典と根拠

ORDレコード
ord-f097c5c239544049a1b4429a3a55b870
出典データセット
uspto-grants-2012_01
特許番号
US08093379B2

反応ノート

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