Hydrazine hydrate (1:1) → [6-(2-Aminomethyl-pyridin-4-yloxy)-benzooxazol-2-yl]-cyclohexylmethyl-amine

HRID 2370508Notes

Reaction equation

HRID 2370508 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][N:26]5C(=O)C6C(=CC=CC=6)C5=O)[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>C(O)C>[NH2:26][CH2:25][C:21]1[CH:20]=[C:19]([O:18][C:16]2[CH:15]=[CH:14][C:12]3[N:13]=[C:9]([NH:8][CH2:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[O:10][C:11]=3[CH:17]=2)[CH:24]=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 674931852-((4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridin-2-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 57725894[6-(2-Aminomethyl-pyridin-4-yloxy)-benzooxazol-2-yl]-cyclohexylmethyl-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 2-((4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridin-2-yl)methyl)-isoindoline-1,3-dione (6.2 mg, 0.013 mmol, 1 eq) was dissolved in 0.5 mL of ethanol. And then hydrazine monohydrate (6.4 mg, 0.13 mmol, 10 eq) was added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. And then the solvents were removed. The crude product was purified by reverse phase prep HPLC to give the title compound. MH+=353.0.

Workup

  1. customAnd then the solvents were removed
  2. customThe crude product was purified by reverse phase prep HPLC

Sources & evidence

ORD record
ord-ae2db42a332d485fb4e557c37719fb7d
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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