HCID 131733647, compound → HCID 118126597, compound

HRID 1752987Notes

Reaction equation

HRID 1752987 reaction equation
[P:1]([O-:47])([O-:46])([O:3][C:4](C(C)(C)C)(C(C)(C)C)[N:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:36])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[O:34][CH3:35])=[CH:7][C:6]1=[O:37])=[O:2]>CC#N.O.CC(O)=O>[P:1]([OH:46])([OH:47])([O:3][CH2:4][N:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:36])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:24])([F:25])[C:20]([F:22])([F:23])[F:21])=[CH:15][C:14]=2[O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[O:34][CH3:35])=[CH:7][C:6]1=[O:37])=[O:2]

Participants

5

Reactant 1

HCID 131733647HCID 131733647, compound

Product 1

HCID 118126597HCID 118126597, compoundYield 43.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ditert-butyl[4-[[2-(4-fluoro-2-methoxy-phenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]-2-oxo-1-pyridyl]methyl phosphate (21) (35 mg, 0.05039 mmol) in CH3CN (700.0 μL), water (700.0 μL) and AcOH (700.0 μL) was refluxed for 1 hour then evaporated to dryness. The material was then co-evaporated with CH3CN (3×), triturated with CH3CN, filtered, washed with CH3CN and desiccated to give [4-[[2-(4-fluoro-2-methoxy-phenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]-2-oxo-1-pyridyl]methyl dihydrogen phosphate (2) (13 mg, 0.02210 mmol, 43.9%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.72 (s, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.63 (d, J=7.6 Hz, 1H), 7.51 (d, J=8.2 Hz, 1H), 7.31 (dd, J=8.9, 5.9 Hz, 1H), 7.16 (dd, J=10.7, 2.9 Hz, 1H), 6.94 (d, J=1.9 Hz, 1H), 6.91-6.84 (m, 1H), 6.77 (s, 1H), 6.47 (dd, J=7.6, 2.2 Hz, 1H), 5.54 (d, J=9.7 Hz, 2H), 3.74 (s, 3H) ppm. 31P NMR (162 MHz, DMSO-d6-85% H3PO4 aq. as internal standard—0 ppm) δ −1.93 (t, J=9.7 Hz, 1H) ppm.

Workup

  1. customthen evaporated to dryness
  2. customtriturated with CH3CN
  3. filtrationfiltered
  4. washwashed with CH3CN

Sources & evidence

ORD record
ord-319d2493373345859f873fd4b889c794
Source dataset
uspto-grants-2015_10
Patent number
US09163042B2

Reaction notes

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