Pyridine → (3-Chloro-4-fluoro-phenyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

HRID 2252753노트

반응식

HRID 2252753 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].N1C=CC=CC=1.S(Cl)([Cl:35])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][Cl:35])=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

5

반응물 3

HCID 1049Pyridine2회HCID 24386Thionyl Chloride2회HCID 11234001{4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

생성물 1

HCID 11383626(3-Chloro-4-fluoro-phenyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

184 mg (0.5 mmol) {4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol are suspended in 15 ml toluene. Pyridine (44 μl, 0.55 mmol) and thionyl chloride (40 μl, 0.55 mmol) are added and the mixture is stirred at RT for 16 h. A second portion of the same amounts of pyridine and thionyl chloride are then added and the mixture stirred for 1 additional hour. The solvent is evaporated and the residue suspended in water containing a small amount of sodium bicarbonate (pH ˜8). After filtration, the product was thoroughly washed with water and ether and dried to give crude title compound; m.p.>300° C.; Rf(dichloromethane/ethanol 95:5 plus 1% conc. ammonia)=0.42; HPLC tR=11.33 min.

후처리

  1. stirringthe mixture stirred for 1 additional hour
  2. customThe solvent is evaporated
  3. filtrationAfter filtration
  4. washthe product was thoroughly washed with water and ether
  5. customdried

출처 및 근거

ORD 기록
ord-d2e049496b7c4ee88c1cfd08813e8f36
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323469B2

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