Ammonia → HCID 68184812, compound

HRID 2409963Notes

Reaction equation

HRID 2409963 reaction equation
[CH:1]1([C:4]2[CH:12]=[C:11]3[C:7]([C:8]([CH2:19][C:20]4[N:25]=[C:24]([C:26](OCC5C=CC=CC=5)=[O:27])[CH:23]=[CH:22][CH:21]=4)=[C:9]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[NH:10]3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[NH3:36]>CO>[CH:1]1([C:4]2[CH:12]=[C:11]3[C:7]([C:8]([CH2:19][C:20]4[N:25]=[C:24]([C:26]([NH2:36])=[O:27])[CH:23]=[CH:22][CH:21]=4)=[C:9]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[NH:10]3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86703282HCID 86703282, compound

Product 1

HCID 68184812HCID 68184812, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl 6-(6-cyclopropyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (200 mg) was dissolved in a solution of ammonia in methanol (about 7 mol/L, 3.3 mL). This solution was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (138 mg). 1H-NMR (CDCl3) δ ppm: 0.69-0.77 (2H, m), 0.92-1.02 (2H, m), 1.97-2.06 (1H, m), 4.42 (2H, s), 5.38-5.59 (1H, br), 6.86 (1H, dd, J=1.4, 8.2 Hz), 7.11-7.15 (1H, m), 7.24-7.29 (1H, m), 7.32-7.48 (4H, m), 7.51-7.58 (2H, m), 7.63-7.71 (1H, m), 7.76-7.96 (1H, br), 7.97-8.03 (1H, m), 8.08 (1H, br).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-120d2a80bf3d45a59f1c699fba4b074c
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

Loading…