Ammonia → HCID 86703284, compound

HRID 2409966Notes

Reaction equation

HRID 2409966 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[NH:7][C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:5]2[CH2:19][C:20]1[N:25]=[C:24]([C:26]([OH:28])=O)[CH:23]=[CH:22][CH:21]=1.C(N1C=CN=C1)([N:31]1C=CN=C1)=O.N.O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[NH:7][C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:5]2[CH2:19][C:20]1[N:25]=[C:24]([C:26]([NH2:31])=[O:28])[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 68751059HCID 68751059, compound

Product 1

HCID 86703284HCID 86703284, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(5-fluoro-6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylic acid (105 mg) in tetrahydrofuran (2.8 mL) was added 1,1′-carbonyldiimidazole (90.5 mg), and this mixture was stirred at room temperature for 9 hours. Then, 28% aqueous ammonia (0.56 mL) was added thereto, followed by stirring at room temperature for 14 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with 10% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain the title compound (103 mg). 1H-NMR (CDCl3) δ ppm: 3.94 (3H, s), 4.37 (2H, s), 5.30-5.60 (1H, br), 6.97 (1H, d, J=7.0 Hz), 7.16 (1H, d, J=11.5 Hz), 7.23-7.28 (1H, m), 7.34-7.41 (1H, m), 7.41-7.49 (2H, m), 7.49-7.57 (2H, m), 7.66-7.94 (2H, m), 7.98-8.13 (2H, m).

Workup

  1. stirringby stirring at room temperature for 14 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with 10% aqueous citric acid solution
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-106ea6a694ad4f5f923dc843ec88dea9
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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