Acetic Acid → HCID 178526365, compound

HRID 1845744Notes

Reaction equation

HRID 1845744 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2C(=O)[O:12][N:11]=[C:10]2[C:15]2[C:19]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8].CCO.[OH-].[Na+].C(O)(=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:15]2[C:19]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][O:17][N:16]=2)=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 589419274-(3-Chloro-4-fluorophenyl)-3-[4-(phenoxymethyl)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 178526365HCID 178526365, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a vial was added 4-(3-chloro-4-fluorophenyl)-3-[4-(phenoxymethyl)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one (9 mg, 23 mmol), EtOH (0.5 mL), and 2.0 M of sodium hydroxide in water (35 μL). Reaction was stirred for 2 hrs at rt. The reaction mixture was neutralized with acetic acid and then purified by preparative HPLC to yield the desired compound (7.6 mg, 90%). 1H NMR (400 MHz, DMSO-d6) δ: 11.58 (s, 1H), 9.05 (s, 1H), 7.32 (t, J=7.8 Hz, 2H) 7.19 (dd, J=9.1, 9.1 Hz, 1H), 7.0 (m, 1H), 6.97 (m, 2 H) 6.96 (m, 1 H), 6.72 (ddd, J=8.8, 4.0, 2.8 Hz, 1H), 5.43 (s, 2H); MF=C16H12ClFN4O3; LCMS calculated for C16H13ClFN4O3(M+H)+: m/z=363.066.

Workup

  1. customReaction
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-33ce070b9f054ac1873139d173be6b1e
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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