4,5-Dimethylisoxazol-3-amine → N-(4,5-dimethylisoxazol-3-yl)-2-[4-(6-fluoroquinolin-4-yloxy)-2-methoxyphenyl]propionamide

HRID 1009763Notes

Reaction equation

HRID 1009763 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:23])[C:20]([OH:22])=O)=[C:15]([O:24][CH3:25])[CH:14]=1.[NH2:26][C:27]1[C:31]([CH3:32])=[C:30]([CH3:33])[O:29][N:28]=1>>[CH3:32][C:31]1[C:27]([NH:26][C:20](=[O:22])[CH:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][C:5]3[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=4)[N:8]=[CH:7][CH:6]=3)=[CH:14][C:15]=2[O:24][CH3:25])[CH3:23])=[N:28][O:29][C:30]=1[CH3:33]

Participants

3

Reactant 2

HCID 841484,5-Dimethylisoxazol-3-amineHCID 673049502-[4-(6-Fluoroquinolin-4-yloxy)-2-methoxyphenyl]propionic acid

Product 1

HCID 67304059N-(4,5-dimethylisoxazol-3-yl)-2-[4-(6-fluoroquinolin-4-yloxy)-2-methoxyphenyl]propionamideYield 11%

Procedure

Using an analogous procedure to that described in Example 2, 2-[4-(6-fluoroquinolin-4-yloxy)-2-methoxyphenyl]propionic acid was reacted with 3-amino-4,5-dimethylisoxazole. The resultant mixture was evaporated and the residue was purified by preparative HPLC using a Waters ‘Xterra’ reversed-phase column (5 microns silica, 30 mm diameter, 150 mm length) using decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound as a solid in 11% yield; 1H NMR: (DMSOd6) 1.43 (s, 3H), 1.77 (s, 3H), 2.3 (s, 3H), 3.81 (s, 3H), 4.16 (q, 1H), 6.72 (d, 1H), 6.87 (m, 1H), 7.0 (d, 1H), 7.4 (d, 1H), 7.75 (m, 1H), 7.97 (m, 1H), 8.12 (m, 1H), 8.7 (d, 1H), 10.16 (s, 1H); Mass Spectrum: M+H+ 436.

Workup

  1. customThe resultant mixture was evaporated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a8bed9d616ad4ff2bf4678bb1dc2b16e
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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