Diazald → HCID 53380165, compound

HRID 1967617Notes

Reaction equation

HRID 1967617 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]=[CH:44][CH:43]=[C:42]([F:46])[C:41]=4[F:47])[C:38]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[C:37]([OH:54])[C:36]3=[O:55])[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]([C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:41]=4[F:47])[C:38]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[C:37]([O:54][CH3:3])[C:36]3=[O:55])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 67387268HCID 67387268, compound

Product 1

HCID 53380165HCID 53380165, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound was synthesized starting from KOH (15 eq in water), diazald (9 eq), ethylene glycol/Et2O (1/2.8 v/v, 34 ml), 1-(1H-Benzo[d]imidazol-6-yl)-5-(2,3-difluorophenyl)-3-hydroxy-4-phenyl-1H-pyrrol-2(5H)-one (1 g, 2.48 mmol, 1 eq) and MeOH (10 ml); yield: 0.160 g (60%); MS m/z: 418.1 [M+H]+; 1H-NMR: (400 MHz, CDCl3) δ: 7.87 (s, 1H), 7.74 (s, 1H), 7.58-7.50 (m, 3H), 7.36-7.2 (m, 5H), 4.18 (s, 3H); HPLC (METHOD [A]): rt 14.70 min (99.68%)

Workup

  1. customThe compound was synthesized
  2. customrt 14.70 min (99.68%)

Sources & evidence

ORD record
ord-8397d606cdca402a981d34422cd923d1
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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