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 1184718Notes

Reaction equation

HRID 1184718 reaction equation
[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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-760935d15c804c299f85d8ee46847063
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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