Methyl iodide → 4-(4-Fluorophenyl)-7-{[{5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-yl}(methyl)amino]methyl}-2H-chromen-2-one

HRID 1988210Notes

Reaction equation

HRID 1988210 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][NH:19][C:20]4[O:21][C:22]([C:25]([OH:32])([C:28]([F:31])([F:30])[F:29])[CH2:26][CH3:27])=[N:23][N:24]=4)=[CH:15][CH:16]=3)[O:11][C:10](=[O:33])[CH:9]=2)=[CH:4][CH:3]=1.CI.[C:36]([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][N:19]([C:20]4[O:21][C:22]([C:25]([OH:32])([C:28]([F:30])([F:31])[F:29])[CH2:26][CH3:27])=[N:23][N:24]=4)[CH3:36])=[CH:15][CH:16]=3)[O:11][C:10](=[O:33])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118561694-(4-fluorophenyl)-7-[({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-yl}amino)methyl]-2H-chromen-2-one

Product 1

HCID 118556254-(4-Fluorophenyl)-7-{[{5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-yl}(methyl)amino]methyl}-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The (−) isomer of 4-(4-fluorophenyl)-7-[({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-yl}amino)methyl]-2H-chromen-2-one (0.100 g, 0.22 mmol), methyl iodide (2 mL) and K2CO3 (0.061 g 0.44 mmol) were heated at 50° C. until the disappearance of starting material. The mixture was cooled to rt and diluted with EtOAc-water. The organic layer was separated, dried and the solvent removed. Purification on silica gel (toluene-acetone, 8:2) gave the title compound. 1H NMR (400 MHz, acetone-d6): δ 7.68 (m, 2H), 7.51 (d, 1H), 7.48 (s, 1H), 7.39 (m, 3H), 6.49 (s, 1H), 6.12 (s, 1H), 4.8 (q, 2H), 3.17 (s, 3H), 2.26 (m, 1H), 2.09 (m, 1H), 1.02 (t, 3H).

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customthe solvent removed
  4. customPurification on silica gel (toluene-acetone, 8:2)

Sources & evidence

ORD record
ord-2d4a85842f44409d9544cf26f4c2473f
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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