4-Aminopyrimidine → 4-chloro-N-(pyrimidin-4-yl)quinoline-7-sulfonamide

HRID 1473413노트

반응식

HRID 1473413 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([S:19](OC3C(F)=C(F)C(F)=C(F)C=3F)(=[O:21])=[O:20])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([S:19]([NH:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][N:3]=3)(=[O:20])=[O:21])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 689584-AminopyrimidineHCID 2733832Lithium HexamethyldisilazideHCID 86687458Perfluorophenyl 4-chloroquinoline-7-sulfonate

생성물 1

HCID 866874614-chloro-N-(pyrimidin-4-yl)quinoline-7-sulfonamide수율 67.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A flask containing a solution of 4-aminopyrimidine (0.026 g, 0.268 mmol) and perfluorophenyl 4-chloroquinoline-7-sulfonate (from Step 2, Intermediate LLLL; 0.100 g, 0.244 mmol) in THF (1.220 ml) was cooled to −78° C. for 10 minutes, and then lithium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (0.488 ml, 0.488 mmol) was added dropwise. After 20 minutes, the reaction had gone to completion. The reaction mixture was quenched with aq ammonium chloride, and concentrated under a vacuum. A 2:1 mixture of DCM:H2O was added, the flask sonicated, and the solids filtered to yield 4-chloro-N-(pyrimidin-4-yl)quinoline-7-sulfonamide (0.053 g, 0.165 mmol, 67.7% yield) as a light brown solid (carried forward crude). m/z (ESI) 321.0 (M+H)+.

후처리

  1. customThe reaction mixture was quenched with aq ammonium chloride
  2. concentrationconcentrated under a vacuum
  3. additionA 2:1 mixture of DCM
  4. additionH2O was added
  5. customthe flask sonicated
  6. filtrationthe solids filtered

출처 및 근거

ORD 기록
ord-82eb3998c80f42eb9221a4af2c845e92
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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