1-Aminoindane, (S)- → 1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-2-((S)-indan-1-ylamino)-ethanol

HRID 1528946Notes

Reaction equation

HRID 1528946 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]2[CH2:16][O:15]2)=[CH:4][CH:3]=1.[C@@H:17]1([NH2:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18]1>CN1CCCC1=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([OH:15])[CH2:16][NH:26][C@@H:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70000841-Aminoindane, (S)-HCID 866524045-(4-Bromo-phenyl)-3-methyl-4-oxiranyl-isoxazole

Product 1

HCID 665786941-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-2-((S)-indan-1-ylamino)-ethanol

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-4-oxiranyl-isoxazole (0.180 g, 0.64 mmol) and (S)-indan-1-ylamine (0.171 g, 1.29 mmol) were mixed in N-methylpyrrolidone (4.0 mL) and then heated to 85° C. over 2 nights while monitoring with analytical LCMS. The reaction was submitted to standard aqueous workup then purified via preparatory HPLC to afford the title compound.

Workup

  1. customthen purified via preparatory HPLC

Sources & evidence

ORD record
ord-28e1a0cde80d42b681fdf152d5961991
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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