Dimethylcarbamoyl Chloride → 5-((4-(Propargyl)piperidin-1-yl)methyl)quinolin-8-yl dimethylcarbamate

HRID 2403465

反応式

HRID 2403465 の反応式
[H-].[Na+].C#CCN1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]3[C:14]=2[CH:15]=[CH:16][CH:17]=[N:18]3)[CH2:8][CH2:7]1.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27]>C1COCC1>[CH3:24][N:25]([CH3:29])[C:26](=[O:27])[O:23][C:20]1[CH:21]=[CH:22][C:13]([CH2:12][N:9]2[CH2:8][CH2:7][CH:15]([CH2:14][C:13]#[CH:12])[CH2:11][CH2:10]2)=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2

参加物

5

反応物 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 6918819Hla-20

生成物 1

HCID 468430605-((4-(Propargyl)piperidin-1-yl)methyl)quinolin-8-yl dimethylcarbamate収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of NaH (24 mg, 0.6 mmol 1.2 equiv) in anhydrous THF, HLA20 (140 mg, 0.5 mmol, 1.0 equiv) was added under Ar at 0° C. The resulting mixture was stirred for 20 min at 0° C. A solution of dimethyl carbamoyl chloride (1.1 equiv) in anhydrous THF was added, and the stirring was continued for 24 h at room temperature. After evaporation of the solvent, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine and dried with NaSO4. Evaporation of the solvent gave a crude product that was purified by RP HPLC.

後処理

  1. additionwas added under Ar at 0° C
  2. waitthe stirring was continued for 24 h at room temperature
  3. customAfter evaporation of the solvent, water
  4. additionwas added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried with NaSO4
  8. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-e7f96697f09a4939978d60fabfd9c626
出典データセット
uspto-grants-2014_08
特許番号
US08802675B2

関連ノート

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