Water → 9-Benzhydryloxy-7-[2-(4-fluoro-phenyl)-ethyl]-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 853708Notes

Reaction equation

HRID 853708 reaction equation
C(O[C:4](=O)[O:5][C:6]1[C:15]2[C:16](=[O:29])[N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:18](=[O:19])[C:14]=2[C:13]([O:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2)C.O.C(=O)([O-])[O-].[K+].[K+].IC>O1CCCC1.C(OCC)(=O)C>[CH:31]([O:30][C:13]1[C:14]2[C:18](=[O:19])[N:17]([CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C:16](=[O:29])[C:15]=2[C:6]([O:5][CH3:4])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 58928851carbonic acid 9-benzhydryloxy-7-[2-(4-fluoro-phenyl)-ethyl]-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester ethyl ester

Product 1

HCID 589287129-Benzhydryloxy-7-[2-(4-fluoro-phenyl)-ethyl]-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To carbonic acid 9-benzhydryloxy-7-[2-(4-fluoro-phenyl)-ethyl]-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester ethyl ester 311 (140 mg, 0.24 mmol) dissolved in tetrahydrofuran (0.50 ml) and water (0.25 ml) was added potassium carbonate (345.4 mg, 2.5 mmol) and N,N-dimethyl-aminopyridine (DMAP, 29.3 mg, 3.8 mmol). After stirring overnight at room temperature, the reaction mixture was concentrated in vacuo and diluted with ethyl acetate. It was then washed twice with 5% citric Acid (aqueous), twice with water, once with brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was dissolved in dimethylformamide (3.0 ml). To this solution was added potassium carbonate (179 mg, 1.3 mmol) and iodomethane (319 mg, 2.6 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with ethyl acetate. It was then washed twice with 5% citric Acid, twice with water, once with brine, and concentrated in vacuo to afford 9-benzhydryloxy-7-[2-(4-fluoro-phenyl)-ethyl]-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione 312 (130 mg, 0.24 mmol, 100%). 1H NMR (CDCl3) δ 9.16 (dd, 1H), 8.58 (dd, 1H), 7.82 (s, 1H), 7.74 (m, 1H), 7.55 (m, 4H), 7.20 (m, 8H), 7.0 (t, 2H), 4.04 (s, 3H), 3.87 (t, 2H), 2.91 (t, 2H). MS: 555.2 (M+23).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washIt was then washed twice with 5% citric Acid (aqueous), twice with water, once with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting residue was dissolved in dimethylformamide (3.0 ml)
  7. stirringAfter stirring overnight at room temperature
  8. washIt was then washed twice with 5% citric Acid, twice with water, once with brine
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62241c585abf446eb385f31b3952ff96
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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