Tert-butyl[(1r)-1-(2,5-difluorobenzyl)-3-(2-isoquinolin-1-ylhydrazino)-3-oxopropyl]carbamate → Tert-butyl[(1r)-1-(2,5-difluorobenzyl)-2-[1,2,4]triazolo[3,4-a]isoquinolin-3-ylethyl]carbamate

HRID 1863957Notes

Reaction equation

HRID 1863957 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]([CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[F:32])[CH2:9][C:10]([NH:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1)=O)([CH3:4])([CH3:3])[CH3:2]>COCCO>[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]([CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[F:32])[CH2:9][C:10]1[N:15]2[CH:16]=[CH:17][C:18]3[C:23]([C:14]2=[N:13][N:12]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 131727791Tert-butyl[(1r)-1-(2,5-difluorobenzyl)-3-(2-isoquinolin-1-ylhydrazino)-3-oxopropyl]carbamate

Product 1

HCID 90963610Tert-butyl[(1r)-1-(2,5-difluorobenzyl)-2-[1,2,4]triazolo[3,4-a]isoquinolin-3-ylethyl]carbamate

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

The crude residue from Step A was treated with 5 mL of 2-methoxyethanol, and the mixture was stirred at reflux for 1 h. The residue obtained upon concentration was flash chromatographed on silica gel (1-2.5% methanol in dichloromethane) to provide the title compound as a light tan solid, mp 185-187° C. (decomposition). LC-MS 439 (M+1).

Workup

  1. temperatureat reflux for 1 h
  2. customThe residue obtained upon concentration
  3. customchromatographed on silica gel (1-2.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a0e51234a29448e693504e5dfab81d0e
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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