Piperidin-4-ol → HCID 59240607, compound

HRID 42200Notes

Reaction equation

HRID 42200 reaction equation
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[N:28][C:27]([C:30]([OH:38])([CH3:37])[CH2:31]OS(C)(=O)=O)=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[N:28][C:27]([C:30]([OH:38])([CH3:37])[CH2:31][N:43]4[CH2:44][CH2:45][CH:40]([OH:39])[CH2:41][CH2:42]4)=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 59240656HCID 59240656, compound

Product 1

HCID 59240607HCID 59240607, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methanesulfonic acid 2-[4-(4-benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl]-2-hydroxy-propyl ester (64 mg, 0.120 mmol) is combined with 4-hydroxy piperidine (61 mg, 0.600 mmol), diisoproylethylamine (63 μL, 0.360 mmol), and acetonitrile (1 mL). The mixture is heated to reflux for 16 h. Concentrate the crude mixture in vacuo. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (15.6 mg, 24%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 16 h
  3. concentrationConcentrate the crude mixture in vacuo
  4. customThe residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4f731da28ef04aac86202e9425f19f9c
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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