Methanol → 2-[(1S)-2-amino-1-(cyclohexylmethyl)ethyl]-5-(1-methyl-1H-pyrazol-5-yl)isoindolin-1-one

HRID 340006Notes

Reaction equation

HRID 340006 reaction equation
[CH:1]1([CH2:7][C@H:8]([N:21]2[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:30]4[N:34]([CH3:35])[N:33]=[CH:32][CH:31]=4)[CH:27]=3)[C:22]2=[O:36])[CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.NN>>[NH2:10][CH2:9][C@@H:8]([N:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:30]3[N:34]([CH3:35])[N:33]=[CH:32][CH:31]=3)[CH:27]=2)[C:22]1=[O:36])[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 866814922-{(2S)-3-cyclohexyl-2-[5-(1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]propyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 715554132-[(1S)-2-amino-1-(cyclohexylmethyl)ethyl]-5-(1-methyl-1H-pyrazol-5-yl)isoindolin-1-oneYield 50.3%

Conditions

Temperature
50 °C

Procedure

A mixture of 2-{(2S)-3-cyclohexyl-2-[5-(1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]propyl}-1H-isoindole-1,3(2H)-dione (30 mg, 0.062 mmol) was dissolved in methanol (3 mL, 70 mmol) and hydrazine (0.3 mL, 10 mmol). The resulting mixture was stirred at 50° C. for 2 h. Direct purification on prep.—HPLC afforded 11 mg (50% yield) of the desired final product. LC-MS found: 353.1 (M+H)+.

Workup

  1. customDirect purification

Sources & evidence

ORD record
ord-8508908d2e09485a9d5f0d4dede02ce8
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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