4-Isoxazolemethanamine → HCID 22274015, compound

HRID 273262Notes

Reaction equation

HRID 273262 reaction equation
[C:1]([NH:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([CH2:24]OS(C)(=O)=O)=[N:22][CH:23]=3)=[C:14]([F:30])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].[O:31]1[CH:35]=[C:34]([CH2:36][NH2:37])[CH:33]=[N:32]1>CN(C=O)C>[F:30][C:14]1[CH:13]=[C:12]([N:8]2[CH2:7][CH:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])[O:10][C:9]2=[O:11])[CH:17]=[CH:16][C:15]=1[C:18]1[CH:23]=[N:22][C:21]([CH2:24][NH:37][CH2:36][C:34]2[CH:33]=[N:32][O:31][CH:35]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 104868034-IsoxazolemethanamineHCID 86596640HCID 86596640, compound

Product 1

HCID 22274015HCID 22274015, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the methanesulfonic acid 5-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-pyridin-2-ylmethyl ester 106 (220 mg, 0.5 mmol) in DMF (4.0 mL) was treated with C-isoxazol-4-yl-methylamine (68 mg, 0.5 mmol, 1.0 equiv) at room temperature, and the resulting reaction mixture was warmed to 60° C. and stirred for 6 hours. When TLC and MS showed the reaction to be complete, the reaction mixture was concentrated in vacuo, and the residue was directly purified by column chromatography (0-5% MeOH/CH2Cl2 gradient elution) to afford the desired N-{3-[3-Fluoro-4-(6-{[(isoxazol-4-ylmethyl)-amino]-methyl}-pyridin-3-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide 4252 (22 mg, 10%) as off-white solids. LCMS (EI): 440 (M++H).

Workup

  1. customthe resulting reaction mixture
  2. customthe reaction
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customthe residue was directly purified by column chromatography (0-5% MeOH/CH2Cl2 gradient elution)

Sources & evidence

ORD record
ord-67529b8e1e384cccb24717eac535e1e6
Source dataset
uspto-grants-2008_11
Patent number
US07456206B2

Reaction notes

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