Water → HCID 86602513, compound

HRID 1726955Notes

Reaction equation

HRID 1726955 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 of 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 day at ambient temperature and then a further 1.6 g potassium carbonate and 3.0 g 3-tert-butoxycarbonylaminopiperidine are added. After another 3 days 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-a3f0700d902944918c728ca72c7f8b09
Source dataset
uspto-grants-2009_02
Patent number
US07495003B2

Reaction notes

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