Water → (2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)piperidine-1-carboximidamide

HRID 75006

반응식

HRID 75006 반응식
Cl.[N:2]1([C:7]([NH2:9])=[NH:8])[CH:6]=[CH:5][CH:4]=N1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:19]([C:20]3[N:25]=[C:24]([NH:26][C@H:27]4CCCN[CH2:28]4)[C:23]([F:33])=[CH:22][N:21]=3)=[CH:18][N:17]([S:34]([C:37]3[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[C:14]2=[N:15][CH:16]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[Cl:10][C:11]1[CH:12]=[C:13]2[C:19]([C:20]3[N:25]=[C:24]([NH:26][CH:27]4[CH2:28][CH2:4][CH2:5][CH2:6][N:2]4[C:7](=[NH:8])[NH2:9])[C:23]([F:33])=[CH:22][N:21]=3)=[CH:18][N:17]([S:34]([C:37]3[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[C:14]2=[N:15][CH:16]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 672851192-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-N-[(3S)-3-piperidyl]pyrimidin-4-amine

생성물 1

HCID 86762735(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)piperidine-1-carboximidamide수율 43.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of pyrazole-1-carboxamidine hydrochloride (0.12 g, 0.80 mmol) and 2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2, 3-13]pyridin-3-yl]-5-fluoro-N-[(3S)-3-piperidyl]pyrimidin-4-amine, 1c, (0.40 g, 0.80 mmol) in DMF (0.9 mL) was added iPr2NEt (0.14 mL, 0.80 mmol). The reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted into water, filtered, washed with additional water, then ether. The filtrate was concentrated in vacuo. The resulting residue was purified by silica gel chromatography using 5-20% MeOH/CH2Cl2 gradient (product elutes with 20% MeOH) to afford 190 mg of the desired product.

후처리

  1. filtrationfiltered
  2. washwashed with additional water
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe resulting residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-70504ba9234d48659ea4c42fc9f1e4a0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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