Water → HCID 12993822, compound

HRID 1835046Notes

Reaction equation

HRID 1835046 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:11]2[NH:12][C:13](=[O:16])[CH2:14][O:15][C:10]=2[CH:9]=[C:8]([F:17])[C:7]=1[N:18]1[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]1=[O:30])=[O:4].[I-].[K+].C(N(CC)C(C)C)(C)C.O>C(#N)C>[CH3:29][N:20]1[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][C:23](=[O:24])[N:18]([C:7]2[C:6]3[NH:5][C:3](=[O:4])[CH2:2][N:12]4[C:13](=[O:16])[CH2:14][O:15][C:10]([C:11]=34)=[CH:9][C:8]=2[F:17])[C:19]1=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 69915983HCID 69915983, compound

Product 1

HCID 12993822HCID 12993822, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-[5-(2-Chloroacetylamino)-7-fluoro-2H-1,4-benzoxazine-3(4H)-on-6-yl]-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (271 mg, 0.60 mmol was dissolved in anhydrous acetonitrile (10 ml) and potassium iodide (14 mg, 0.08 mmol) and N,N-diisopropylethylamine (100.8 mg, 0.78 mmol) were added. Solution was refluxed for 2 hr. added to water and extracted with ethyl acetate. Product was purified by flash chromatography on silica gel with hexane-ethyl acetate (1:1) as eluent (218.6 mg, 0.53 mmol).

Workup

  1. temperatureSolution was refluxed for 2 hr
  2. extractionextracted with ethyl acetate
  3. customProduct was purified by flash chromatography on silica gel with hexane-ethyl acetate (1:1) as eluent (218.6 mg, 0.53 mmol)

Sources & evidence

ORD record
ord-43d0ef26c39e40179d492722044c5130
Source dataset
uspto-grants-2004_08
Patent number
US06770596B1

Reaction notes

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