Diazald → HCID 178488638, compound

HRID 2388589Notes

Reaction equation

HRID 2388589 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]=[CH:32][C:33]([N:35]3[CH:39]([C:40]4[CH:45]=[C:44]([F:46])[C:43]([F:47])=[CH:42][C:41]=4[F:48])[C:38]([CH3:49])=[C:37]([OH:50])[C:36]3=[O:51])=[CH:34][C:29]=2[N:28]=[CH:27]1>CO>[NH:26]1[C:30]2[CH:31]=[CH:32][C:33]([N:35]3[CH:39]([C:40]4[CH:45]=[C:44]([F:46])[C:43]([F:47])=[CH:42][C:41]=4[F:48])[C:38]([CH3:49])=[C:37]([O:50][CH3:3])[C:36]3=[O:51])=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 178431716HCID 178431716, compound

Product 1

HCID 178488638HCID 178488638, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound was synthesized starting from KOH (15 g, 267.8 mmol in water), diazald (20 g, 93.37 mmol 5 eq) ethylene glycol/Et2O (2/1 v/v, 140 mL), 1-(1H-benzo[d]imidazol-5-yl)-5-(2,4,5-trifluorophenyl)-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (2 g, 5.57 mmol, 1 eq) and MeOH (50 mL); yield: 1.05 g (50.55%); MS m/z: 374.0 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 12.44 (s, 1H); 8.17 (s, 1H); 7.66 (s, 1H), 7.52-7.10 (m, 4H); 6.00 (s, 1H); 3.96 (s, 3H); 1.78 (s, 3H); HPLC (METHOD [A]): rt 12.37 min (98.7%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.37 min (98.7%)

Sources & evidence

ORD record
ord-5c37392e2f25465aa2c3eb1e3483d3bf
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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