Dimethylformamide → 4-{2-[5-Chloro-2-(4-methanesulfonyl-piperazin-1-yl)-pyrimidin-4-yl]-1-hydroxy-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1184718노트

반응식

HRID 1184718 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:24])[CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18](Cl)[N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:26][S:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])=[O:28].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:24])[CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([N:33]3[CH2:34][CH2:35][N:30]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:31][CH2:32]3)[N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 162656121-Methanesulfonylpiperazine hydrochlorideHCID 866749004-[2-(2,5-Dichloro-pyrimidin-4-yl)-1-hydroxy-ethyl]-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 679734844-{2-[5-Chloro-2-(4-methanesulfonyl-piperazin-1-yl)-pyrimidin-4-yl]-1-hydroxy-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of 4-[2-(2,5-dichloro-pyrimidin-4-yl)-1-hydroxy-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (100 mg), 1-methanesulfonyl-piperazine hydrochloride (70 mg), potassium carbonate (100 mg), and N,N-dimethylformamide (1 mL) is stirred for 4 h at 60° C. After cooling to room temperature ethyl acetate is added. The organic phase is separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100) to give the title compound. LC (method 7): tR=1.46 min; Mass spectrum (ESI+): m/z=504 [M+H]+.

후처리

  1. additionis added
  2. customThe organic phase is separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100)

출처 및 근거

ORD 기록
ord-760935d15c804c299f85d8ee46847063
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669271B2

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