o-Toluenesulfonyl chloride → 7-(3-Chloro-propylsulfanyl)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

HRID 8261

반응식

HRID 8261 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25][CH2:26][CH2:27][CH2:28]O)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.C1(C)C(S([Cl:39])(=O)=O)=CC=CC=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Cl:39][CH2:28][CH2:27][CH2:26][S:25][C:21]1[CH:20]=[C:19]2[C:24]([C:15]([C:8]3[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:11][N:10]4[CH2:12][CH2:13][CH2:14][C:9]=34)=[CH:16][CH:17]=[N:18]2)=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 8623o-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 219925373-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylsulfanyl]-propan-1-ol

생성물 1

HCID 101591567-(3-Chloro-propylsulfanyl)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of Preparation #21, 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylsulfanyl]-propan-1-ol (25.0 mg, 0.062 mmol) in dry pyridine (0.1 mL) is added toluene sulfonyl chloride (60.0 mg, 0.31 mmol) and the resulting mixture stirred at room temperature for 72 h. Saturated sodium bicarbonate solution is added and the resulting solution extracted with ethyl acetate. The organic layer is washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification of the residue on SiO2 (5% to 10% methanol in dichloromethane) gives the desired product, 11.2 mg (43%). MS ES+ m/e 421.1 (M+1).

후처리

  1. extractionthe resulting solution extracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue on SiO2 (5% to 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-cb9b6c262d904ba286a664c696baaedc
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

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