Glyoxal → HCID 57161676, compound

HRID 1439949Notes

Reaction equation

HRID 1439949 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[N:23]=[N:24][CH:25]=[CH:26]C=3)[C@H:16]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.S([O-])([O-])(=O)=O.[Mg+2].C([N:44](CC)CC)C.C(C=O)=O>C(O)C>[F:34][C:2]([F:35])([F:1])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[N:23]=[N:24][CH:25]=[CH:26][N:44]=3)[C@H:16]2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

6

Reactant 4

HCID 7860GlyoxalHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 15816402HCID 15816402, compound

Product 1

HCID 57161676HCID 57161676, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The amidrazone hydrochloride of (b) above (200 mg) was dissolved in ethanol (2 ml). Magnesium sulphate was added (100 mg) and the mixture stirred for 30 min. Triethylamine (0.06 ml) was added followed by glyoxal (90 mg, trimeric dihydrate). This mixture was allowed to stir for 12 h. The solvent was removed in vacuo and the residue was dispersed between ethyl acetate and water. The organic layer was dried (MgSO4) and concentrated to afford a brown oil. This was purified by column chromatography on silica using hexane in ethyl acetate (95%) to afford the title compound. 1H NMR (360 MHz, CDCl3) δ 1.53-1.72 (2H, m, CH2), 1.98-2.22 (2H, m, CH2), 2.42-2.53 (1H, m, NCHH), 3.14-3.22 (1H, m, NCHH), 3.61 (1H, bs, CHO), 3.74-3.81 (2H, m, NCHPh+OCHH), 4.04 (1H, d, J=12 Hz, NCHHtriazine), 4.19 (1H, d, J=12 Hz, OCHH), 4.47 (1H, d, J=12 Hz, NCHHtriazine), 7.24-7.37 (4H, m, ArH), 7.48-7.6 (4H, m, ArH), 7.70 (1H, s, ArH), 8.6 (1H, s, ArH). MS (CI+) m/z 497 (M+ 1, 100%). The following examples illustrate pharmaceutical compositions according to the invention.

Workup

  1. stirringto stir for 12 h
  2. customThe solvent was removed in vacuo
  3. additionthe residue was dispersed between ethyl acetate and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customto afford a brown oil
  7. customThis was purified by column chromatography on silica

Sources & evidence

ORD record
ord-6c3a7bf1d97847a0bc55834c83c7e944
Source dataset
uspto-grants-1996_03
Patent number
US05496833

Reaction notes

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