3-Isoxazolamine, 5-(1,1-dimethylethyl)- → HCID 24953743, compound

HRID 2076802Notes

Reaction equation

HRID 2076802 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][C@@H:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10]2)=[CH:4][CH:3]=1.[C:21]([C:25]1[O:29][N:28]=[C:27]([NH2:30])[CH:26]=1)([CH3:24])([CH3:23])[CH3:22].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CS(C)=O>[C:21]([C:25]1[O:29][N:28]=[C:27]([NH:30][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][N:9]3[CH2:14][CH2:13][O:12][C@@H:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:10]3)=[CH:6][N:7]=2)[CH:26]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 2724254Sodium bis(trimethylsilyl)amideHCID 59177295HCID 59177295, compound

Product 1

HCID 24953743HCID 24953743, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

2.73 mL of (S)-4-(6-Chloro-pyridin-3-ylmethyl)-2-phenyl-morpholine in DMSO(0.1M solution) was added to 63 mg of 5-tert-Butyl-isoxazol-3-ylamine. 900 L of sodium bis(trimethylsilyl)amide (1M solution in tetrahydrofuran) was added and the reaction heated overnight at 60° C. on an orbital shaker. The reaction was filtered through a fritted cartridge. Purification was accomplished by preparatory liquid chromatography to give the title compound in 24% yield. EI m/z 393=MH+

Workup

  1. filtrationThe reaction was filtered through a fritted cartridge
  2. customPurification

Sources & evidence

ORD record
ord-a8b8860f62c44208a1608f90c159c538
Source dataset
uspto-grants-2011_04
Patent number
US07928103B2

Reaction notes

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