Diazald → HCID 178488724, compound

HRID 2388588Notes

Reaction equation

HRID 2388588 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[C:45]([F:46])=[CH:44][CH:43]=[CH:42][C:41]=4[F:47])[C:38]([CH3:48])=[C:37]([OH:49])[C:36]3=[O:50])[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[C:41]([F:47])=[CH:42][CH:43]=[CH:44][C:45]=4[F:46])[C:38]([CH3:48])=[C:37]([O:49][CH3:3])[C:36]3=[O:50])=[CH:31][C:30]=2[N:26]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 57923985HCID 57923985, compound

Product 1

HCID 178488724HCID 178488724, 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-(2,6-difluorophenyl)-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (0.189 g, 0.5 mmol, 1 eq) and MeOH/H2O (90/10 v/v); yield: 0.058 g (32.6%); MS m/z: 356.3 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 1.65-1.81 (s, 3H), 3.83-3.93 (s, 3H), 6.14 (s, 1H), 6.83-7.78 (m, 6H), 8.15 (s, 1H), 12.07-12.07 (bs, 1H); HPLC (METHOD [A]): rt 11.24 min (99%)

Workup

  1. customThe compound was synthesized
  2. customrt 11.24 min (99%)

Sources & evidence

ORD record
ord-2a4917fc58704dcc87bac7ca7f7b1124
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

Loading…