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

HRID 2403465

반응식

HRID 2403465 반응식
[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

참가 물질

5

반응물 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 6918819Hla-20

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e7f96697f09a4939978d60fabfd9c626
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802675B2

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