Diazald → HCID 53379981, compound

HRID 1967607Notes

Reaction equation

HRID 1967607 reaction equation
[OH-].[K+].[CH3:3]C1C=CC(S(N(N=O)C)(=O)=O)=CC=1.C(O)CO.CCOCC.[NH:26]1[C:30]2[CH:31]=[C:32]([N:35]3[CH:39]([CH:40]([CH3:42])[CH3:41])[C:38]([CH3:43])=[C:37]([OH:44])[C:36]3=[O:45])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1>CO>[NH:26]1[C:30]2[CH:31]=[C:32]([N:35]3[CH:39]([CH:40]([CH3:42])[CH3:41])[C:38]([CH3:43])=[C:37]([O:44][CH3:3])[C:36]3=[O:45])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 67387135HCID 67387135, compound

Product 1

HCID 53379981HCID 53379981, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound was synthesized starting from KOH (15 eq in water), diazald (8 eq), ethylene glycol/Et2O (1/2 v/v, 30 ml), 1-(1H-Benzo[d]imidazol-6-yl)-5-isopropyl-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (0.500 g, 1.83 mmol, 1 eq) and MeOH (10 ml); yield: 0.040 g (7.6%); MS m/z: 286.1 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 0.54 (d, 3H), 0.94-0.92 (q, 3H), 1.95 (t, 3H), 3.86 (s, 1H), 4.73 (s, 1H), 7.26-7.15 (m, 1H), 7.65-7.51 (m, 2H), 8.22 (d, 1H), 12.46 (d, 1H); HPLC (METHOD [A]): rt 8.32 min (96.64%)

Workup

  1. customThe compound was synthesized
  2. customrt 8.32 min (96.64%)

Sources & evidence

ORD record
ord-fac02b3b4b614ba3ad9e8f33f1f1c6c0
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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