Acetic Acid → 5-Methyl-1,10-diazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-12-one

HRID 1266019Notes

Reaction equation

HRID 1266019 reaction equation
[O:1]=[C:2]1[N:13]2[C:14]3[C:10]([CH:11]=[CH:12]2)=[C:9]([CH2:15]OC(=O)C)[CH:8]=[CH:7][C:6]=3[CH2:5][NH:4][CH2:3]1.CC(O)=O>CO.[Pd]>[CH3:15][C:9]1[CH:8]=[CH:7][C:6]2[CH2:5][NH:4][CH2:3][C:2](=[O:1])[N:13]3[C:14]=2[C:10]=1[CH:11]=[CH:12]3

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69701052Acetic acid-1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-7-ylmethyl ester

Product 1

HCID 697023235-Methyl-1,10-diazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-12-oneYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Acetic acid-1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-7-ylmethyl ester (0.508 g, 1.97 mmol) was dissolved in MeOH (70 mL) and glacial AcOH (30 mL). To the solution was added 10% Pd/C (0.076 g) and the suspension was stirred under an atmosphere of H2 for 4.5 h at rt. The black suspension was filtered and the filtrate was concentrated to give a white solid, which was purified by flash silica gel chromatography eluting with a gradient of 0-1% MeOH in CHCl3 to give 0.296 g (75%) of the title compound: 1H NMR (DMSO-d6) δ 2.52 (s, 3H), 3.51-3.54 (m, 2H), 4.27-4.28 (m, 2H), 7.11 (t, 1H, J=7.5 Hz), 7.15 (s, 1H), 7.69 (d, 1H, J=7.5 Hz), 7.81 (d, 1H, J=7.5 Hz), 8.22-8.24 (m, 1H). HRMS calcd. for C12H12N2O (M+) 200.0950, found 200.0955. Anal. (C12H12N2O) C, H, N.

Workup

  1. filtrationThe black suspension was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give a white solid, which
  4. customwas purified by flash silica gel chromatography
  5. washeluting with a gradient of 0-1% MeOH in CHCl3

Sources & evidence

ORD record
ord-1a59bf28f226406db2902fb5230142e4
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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