HCID 57513874, compound → HCID 57513873, compound

HRID 2262726Notes

Reaction equation

HRID 2262726 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:39])[CH2:12][N:13]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20](=[O:27])[N:19]4CC4C=CC(OC)=CC=4OC)[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:39])[CH2:12][N:13]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20](=[O:27])[NH:19]4)[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 1

HCID 57513874HCID 57513874, compound

Product 1

HCID 57513873HCID 57513873, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

At 0° C., 1′-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-2-(2,4-dimethoxybenzyl)spiro [isoindole-1,4′-piperidin]-3(2H)-one (1.4 mmol) is added to trifluoroacetic acid (10 ml) and the resulting solution is heated at 60° C. for 4 h. Solvent is removed and the residue is partitioned between aqueous NaHCO3 solution (20 ml) and EtOAc (20 ml). The layers are separated and the aqueous layer is extracted with EtOAc (20 ml). The combined extracts are washed with brine (20 ml), dried over Na2SO4 and evaporated. The residue is purified by flash column to give the title compound as a off-white solid. LC-MS (M+1): 382.2.

Workup

  1. customSolvent is removed
  2. customthe residue is partitioned between aqueous NaHCO3 solution (20 ml) and EtOAc (20 ml)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (20 ml)
  5. washThe combined extracts are washed with brine (20 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue is purified by flash column

Sources & evidence

ORD record
ord-3723d907a1c74d3b8e433633fd507d07
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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