HCID 86679488, compound → HCID 86679489, compound

HRID 1776530Notes

Reaction equation

HRID 1776530 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=2[N:26]([CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)[S:27]([CH3:30])(=[O:29])=[O:28])[C:9]([O:11][CH2:12][C:13]([O:15]CC2C=CC=CC=2)=[O:14])=[O:10])[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=2[N:26]([CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)[S:27]([CH3:30])(=[O:28])=[O:29])[C:9]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86679488HCID 86679488, compound

Product 1

HCID 86679489HCID 86679489, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of 2-(benzyloxy)-2-oxoethyl 3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin-1-yl)ethyl)methylsulfonamido)benzoate (370 mg, 0.661 mmol) and a catalytic amount of 10% Pd/C in MeOH (20 ml) was hydrogenated at 20 psi for 2 hours. The catalyst was filtered off and the solvent was evaporated to give 2-(3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin-1-yl)ethyl)methylsulfonamido)-benzoyloxy)acetic acid (270 mg, 0.575 mmol, 87% yield, MS/ESI+ 470.0 [MH]+) that was used in the following step without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6cb9d3de79e149c09c6862628af53f7b
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…