Glyoxal → HCID 57161676, compound

HRID 1757247Notes

Reaction equation

HRID 1757247 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) δ1.53-1.72 (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%).

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-1bae4a0a87fa4b8fb9bdcb36d2365925
Source dataset
uspto-grants-1995_08
Patent number
US05444074

Reaction notes

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