Iodoethane → FDL169

HRID 1428933Notes

Reaction equation

HRID 1428933 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[C:11](=[O:19])[N:10]([CH2:20][C:21]([N:23]([CH3:34])[C:24]3[CH:33]=[CH:32][C:27]4[N:28]=[C:29]([CH3:31])[O:30][C:26]=4[CH:25]=3)=[O:22])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:41](I)[CH3:42]>CN(C=O)C.O>[CH2:41]([O:18][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][N:10]([CH2:20][C:21]([N:23]([CH3:34])[C:24]3[CH:33]=[CH:32][C:27]4[N:28]=[C:29]([CH3:31])[O:30][C:26]=4[CH:25]=3)=[O:22])[C:11]2=[O:19])=[CH:16][CH:15]=1)[CH3:42]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 136346960HCID 136346960, compound

Product 1

HCID 86298861FDL169Yield 50.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(4-(3-fluorophenyl)-7-hydroxy-1-oxophthalazin-2(1H)-yl)-N-methyl-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (6.5 g, 14.19 mmol) was dissolved in DMF (60 mL), treated with K2CO3 (3.04 g, 21.2 mmol) and stirred at rt for 30 min. After cooling to 0° C., EtI (1.26 mL, 15.59 mmol) was added dropwise and the reaction was warmed to rt for 1 h. It was diluted with water (20 mL) and extracted with EtOAc (2×15 mL). The organics were washed with brine (300 mL), dried over Na2SO4, and concentrated to give crude material which was purified by chromatography (40% EtOAc/hexane) to yield 2-(7-ethoxy-4-(3-fluorophenyl)-1-oxophthalazin-2(1H)-yl)-N-methyl-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (3.5 g) (487.52 [M+H]). 1H NMR: (400 MHz, DMSO) δ: 1.39-1.42 (t, 3H), 2.62 (s, 3H), 3.24 (s, 3H), 4.22-4.24 (d, J=7.2, 2H), 4.72 (s, 2H), 7.37-7.49 (m, 5H), 7.58-7.65 (m, 3H), 7.71-7.73 (d, J=8.4, 1H), 7.90 (s, 1H).

Workup

  1. temperatureAfter cooling to 0° C.
  2. temperaturethe reaction was warmed to rt for 1 h
  3. extractionextracted with EtOAc (2×15 mL)
  4. washThe organics were washed with brine (300 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give crude material which
  8. customwas purified by chromatography (40% EtOAc/hexane)

Sources & evidence

ORD record
ord-185b6f41f2204b0ca447ab6bb4a0f46f
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

Loading…