Water → HCID 86602513, compound

HRID 2378079Notes

Reaction equation

HRID 2378079 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]([CH2:19][C:20]#[C:21][CH3:22])[C:8](=[N:16][C:17]#[N:18])OC1C=CC=CC=1)=[O:5])[CH3:2].[C:23]([O:27][C:28]([NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][NH:33][CH2:32]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:23]([O:27][C:28]([NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][N:33]([C:8]([N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:19][C:20]#[C:21][CH3:22])=[N:16][C:17]#[N:18])[CH2:32]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 42330413-(Boc-amino)piperidine2×HCID 86087963HCID 86087963, compound

Product 1

HCID 86602513HCID 86602513, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g 1-ethoxycarbonylmethyl-1-(but-2-ynyl)-3-cyano-2-phenyl-isourea are added to a mixture of 10.0 g 3-tert-butoxycarbonylaminopiperidine and 4.8 g potassium carbonate in 50 ml of dimethylformamide. The reaction mixture is stirred for 1 d at ambient temperature and then a further 1.6 g potassium carbonate and 3.0 g 3-tert-butoxycarbonylaminopiperidine are added. After another 3 d at ambient temperature water is added and the mixture is extracted with ethyl acetate. The organic extracts are dried over sodium sulphate, the solvent is removed, and the residue is purified on silica gel (cyclohexane/ethyl acetate 5:1->1:2).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe organic extracts are dried over sodium sulphate
  3. customthe solvent is removed
  4. customthe residue is purified on silica gel (cyclohexane/ethyl acetate 5:1->1:2)

Sources & evidence

ORD record
ord-ba2ed3d56be340c3b861475d7bfcf255
Source dataset
uspto-grants-2008_12
Patent number
US07470716B2

Reaction notes

Loading…