Diazald → HCID 53380069, compound

HRID 1967611Notes

Reaction equation

HRID 1967611 reaction equation
[OH-].[K+].[CH3:3]C1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[NH:17]1[C:21]2[CH:22]=[C:23]([N:26]3[CH:30]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=4[Cl:39])[C:29]([C:40]4C=CC=CC=4)=[C:28]([OH:46])[C:27]3=[O:47])[CH:24]=[CH:25][C:20]=2[N:19]=[CH:18]1>CO.O>[NH:17]1[C:21]2[CH:22]=[C:23]([N:26]3[CH:30]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=4[Cl:39])[C:29]([CH3:40])=[C:28]([O:46][CH3:3])[C:27]3=[O:47])[CH:24]=[CH:25][C:20]=2[N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 67387304HCID 67387304, compound

Product 1

HCID 53380069HCID 53380069, 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-chloro-3,6-difluorophenyl)-3-hydroxy-4-phenyl-1H-pyrrol-2(5H)-one (0.103 g, 0.25 mmol, 1 eq) and MeOH/H2O (90/10 v/v); yield: 0.013 g (13.3%); MS m/z: 390.2 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 1.78, 1.81 (2s, 3H), 3.94, 3.95 (2s, 3H), 6.34-6.35 (m, 1H), 7.11-7.17 (m, 1H), 7.25-7.29 (m, 1H), 7.35-7.40 (m, 1H), 7.52-7.54 (m, 1H), 7.67 (s, 1H), 8.35 (s, 1H); HPLC (METHOD [A]): rt 12.59 min (95%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.59 min (95%)

Sources & evidence

ORD record
ord-8b118b873c7d419a97c612ed95ef507c
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

Loading…