Methanol → HCID 11661729, compound

HRID 506777Notes

Reaction equation

HRID 506777 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:21]3[N:29](S(C4C=CC(C)=CC=4)(=O)=O)[C:24]4=[N:25][CH:26]=[CH:27][CH:28]=[C:23]4[CH:22]=3)=[CH:10][N:11]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[C:6]2=[CH:5][C:4]=1[O:40][CH3:41].CO>[OH-].[K+]>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:21]3[NH:29][C:24]4=[N:25][CH:26]=[CH:27][CH:28]=[C:23]4[CH:22]=3)=[CH:10][N:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)[C:6]2=[CH:5][C:4]=1[O:40][CH3:41]

Participants

4

Reactant 2

HCID 887MethanolHCID 68466412HCID 68466412, compound

Product 1

HCID 11661729HCID 11661729, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Bring bisazaindole 21 (10 mg, 0.017 mmol) to reflux in KOH at 3%/MeOH (10 mL) for 5 h. Concentrate the reaction mixture, dilute the residue with H2O, add 2N HCl to adjust the pH to 8, extract with CH2Cl2, dry (MgSO4) and concentrate. Purification by flash chromatography leads to 22 (3.4 mg, 46.6%) as an ivory-colored solid: 1H NMR (CDCl3) δ 10.77 (s broad, 1H), 8.22 (d, 1H, J=4.5 Hz), 7.84 (d, 1H, J=7.4 Hz), 7.59 (s, 1H), 7.15 (s, 1H), 7.03 (m, 1H), 6.58 (d, 1H, J=1.2 Hz), 4.73 (s, 3H), 4.25 (s, 3H) overlapping with (t, 2H), 3.99 (s, 3H), 2.80 (t, 2H), 2.51 (m broad, 8H). TLC (MeOH at 10%/CH2Cl2, 0.25% of NH3) Rf=0.40, m/z obs.=421.14 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture
  2. additiondilute the residue with H2O
  3. additionadd 2N HCl
  4. extractionextract with CH2Cl2
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-0e4966c4090b4e07a4602f17ff4f4c3a
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

Loading…