HCID 66677904, compound → 1-(4-(5-(4-(Methoxycarbonyl)-3-(pyridin-2-yl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid

HRID 1951954Notes

Reaction equation

HRID 1951954 reaction equation
C([O:5][C:6]([CH:8]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:23]=[C:22]([C:24]4[O:28][N:27]=[C:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)[C:25]=4[C:35]([O:37][CH3:38])=[O:36])[O:21][N:20]=3)=[CH:15][CH:14]=2)[CH2:9]1)=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[CH3:38][O:37][C:35]([C:25]1[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=[N:27][O:28][C:24]=1[C:22]1[O:21][N:20]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][N:10]3[CH2:11][CH:8]([C:6]([OH:7])=[O:5])[CH2:9]3)=[CH:14][CH:15]=2)[N:23]=1)=[O:36]

Participants

3

Reactant 1

HCID 66677904HCID 66677904, compound

Product 1

HCID 468471491-(4-(5-(4-(Methoxycarbonyl)-3-(pyridin-2-yl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acidYield 92.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl 5-(3-(4-((3-(tert-butoxycarbonyl)azetidin-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)-3-(pyridin-2-yl)isoxazole-4-carboxylate (79 mg, 0.153 mmol) in trifluoroacetic acid (2 mL) was allowed to stand at room temperature for 1 h. The volatiles were removed under reduced pressure, and the residue was suspended in water. The pH was adjusted to ˜4 with a 1N aqueous solution of sodium hydroxide, and the resulting suspension was allowed to stir briskly overnight. Filtration and drying afforded 1-(4-(5-(4-(methoxycarbonyl)-3-(pyridin-2-yl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid (65 mg, 0.141 mmol, 92% yield) as a slightly off-white powder. HPLC retention time=2.51 minutes (YMC-Combi 4.6×50 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.2% phosphoric acid over a 4 minute gradient. MS: (M+H)=462.18. 1H NMR (500 MHz, MeOD) δ ppm 3.61-3.68 (m, 1H), 3.98 (s, 3H), 4.30-4.37 (m, 4H), 4.50 (s, 2H), 7.53-7.56 (m, 1H), 7.68 (d, J=8.3 Hz, 2H), 7.98-8.02 (m, 1H), 8.09 (d, J=7.7 Hz, 1H), 8.26 (d, J=8.8 Hz, 2H), and 8.69 (d, J=4.4 Hz, 1H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. filtrationFiltration
  3. customdrying

Sources & evidence

ORD record
ord-a77ccc72ab704316892c9b36ed894743
Source dataset
uspto-grants-2013_03
Patent number
US08404672B2

Reaction notes

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