Diazald → HCID 178486597, compound

HRID 1967609Notes

Reaction equation

HRID 1967609 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]([C:40]4[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[C:41]=4[F:48])[C:38]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)=[C:37]([OH:55])[C:36]3=[O:56])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1>CO.O>[NH:28]1[C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH:39]([C:40]4[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[C:41]=4[F:48])[C:38]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)=[C:37]([O:55][CH3:3])[C:36]3=[O:56])=[CH:31][C:30]=2[N:26]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 57923923HCID 57923923, compound

Product 1

HCID 178486597HCID 178486597, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The compound was synthesized starting from KOH (10 eq in water), diazald (5 eq), ethylene glycol/Et2O (3/1 v/v), 1-(1H-benzo[d]imidazol-6-yl)-5-(2,3,5-trifluorophenyl)-3-hydroxy-4-phenyl-1H-pyrrol-2(5H)-one (0.230 g, 0.5 mmol, 1 eq) and MeOH/H2O (90/10 v/v); yield: 0.015 g (6.9%); MS m/z: 436.4 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 4.11 (s, 1H), 6.94 (s, 1H), 7.22-7.42 (m, 6H), 7.58-7.68 (m, 3H), 7.73-7.76 (m, 1H), 7.95 (s, 1H), 9.07 (s, 1H); HPLC (METHOD [A]): rt 15.38 min (82%)

Workup

  1. customThe compound was synthesized
  2. customrt 15.38 min (82%)

Sources & evidence

ORD record
ord-860d1797b06543ef848b627b6c7bb32f
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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