Hydrazine → 6-[(1S)-2-amino-1-(3-fluorobenzyl)ethyl]-2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

HRID 339996Notes

Reaction equation

HRID 339996 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:38])[C:6]=1[C:7]1[N:12]=[C:11]2[CH2:13][N:14]([C@@H:17]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[C:15](=[O:16])[C:10]2=[CH:9][CH:8]=1.NN>CO>[NH2:19][CH2:18][C@@H:17]([N:14]1[C:15](=[O:16])[C:10]2[C:11](=[N:12][C:7]([C:6]3[N:5]([CH3:38])[N:4]=[CH:3][C:2]=3[Cl:1])=[CH:8][CH:9]=2)[CH2:13]1)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 866814822-[(2S)-2-[2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-5-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 715552636-[(1S)-2-amino-1-(3-fluorobenzyl)ethyl]-2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

2-[(2S)-2-[2-(4-Chloro-1-methyl-1H-pyrazol-5-yl)-5-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione (0.050 g, 0.094 mmol) was dissolved in methanol (2 mL), and hydrazine (0.06 g, 2 mmol) was added. The reaction was stirred at 60° C. for 2 hr. After concentration, the residue was purified by pH=10 Prep.—HPLC to give the desired product as white powder. LC-MS found: 400.1 (M+H)+.

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by pH=10 Prep.—HPLC

Sources & evidence

ORD record
ord-461b8f710e9d404d93d2fc2140b5ec29
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

Loading…