Dimethylformamide → HCID 58928667, compound

HRID 853670Notes

Reaction equation

HRID 853670 reaction equation
[CH:1]([O:14][C:15]1[C:26]2[C:25](=[O:27])[N:24]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:23](=[O:36])[C:22]=2[C:21]([OH:37])=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:45]N(C=O)C.C([O-])([O-])=O.[K+].[K+].CI>O>[CH:1]([O:14][C:15]1[C:26]2[C:25](=[O:27])[N:24]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[C:23](=[O:36])[C:22]=2[C:21]([O:37][CH3:45])=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58928995HCID 58928995, compound

Product 1

HCID 58928667HCID 58928667, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzhydryloxy-1-benzyl-6-(4-fluoro-benzyl)-8-hydroxy-1H-1,3,6-triaza-s-indacene-5,7-dione 258 (103 mg, 0.177 mmol, 1 equiv.) was added to a flask containing DMF (4 mL) followed by K2CO3 (122 mg, 0.88 mmol, 5 equiv.). To this was added methyl iodide (MeI, 109 μL, 1.76 mmol, 10 equiv.) under a nitrogen atmosphere and stirred for 16 hours. To the reaction was added water (50 mL) and extracted with ethyl acetate (2×40 mL). The organic layer was washed several times with water (3×30 mL), saturated NaHCO3 (40 mL), brine solution (30 mL). It was dried over Na2SO4, filtered and concentrated in vacuo and purified by silica gel chromatography using 7/3 Hexanes/Ethyl acetate to obtain 4-benzhydryloxy-1-benzyl-6-(4-fluoro-benzyl)-8-methoxy-1H-1,3,6-triaza-s-indacene-5,7-dione 259 (73%, 75 mg, 0.125 mmol). 1H NMR (300 MHz) CDCl3 δ 8.09 (s, 1 H), 7.94 (s, 1 H), 7.88 (s, 1 H), 7.64-7.43 (m, 4 H), 7.41-7.46 (m, 2 H), 7.17-7.43 (m, 10 H), 6.98-7.04 (m, 3 H), 5.56 (s, 2 H), 4.80 (s, 2 H), 3.84 (s, 3 H). MS: 620.1 (M+23). TLC Rf: 0.6 Hexanes/Ethyl acetate (1/1).

Workup

  1. extractionextracted with ethyl acetate (2×40 mL)
  2. washThe organic layer was washed several times with water (3×30 mL), saturated NaHCO3 (40 mL), brine solution (30 mL)
  3. dry with materialIt was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-67dc2033a16c4eb0863a6e73db1f6658
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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