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

HRID 1922215Notes

Reaction equation

HRID 1922215 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-330efd8eb04940558c0f7178377c3e1d
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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