Diazald → HCID 178486598, compound

HRID 1967624Notes

Reaction equation

HRID 1967624 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[CH:32]=[N:33][C:34]5[C:39]([CH:40]=4)=[CH:38][CH:37]=[CH:36][CH:35]=5)[C:29]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[C:28]([OH:47])[C:27]3=[O:48])[CH:24]=[CH:25][C:20]=2[N:19]=[CH:18]1>CO.O>[NH:19]1[C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH:30]([C:31]4[CH:32]=[N:33][C:34]5[C:39]([CH:40]=4)=[CH:38][CH:37]=[CH:36][CH:35]=5)[C:29]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)=[C:28]([O:47][CH3:3])[C:27]3=[O:48])=[CH:22][C:21]=2[N:17]=[CH:18]1

Participants

5

Reactant 3

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 57924139HCID 57924139, compound

Product 1

HCID 178486598HCID 178486598, 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-(quinolin-3-yl)-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: 0.003 g (1.4%); MS m/z: 433.4 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 4.17 (s, 3H), 6.85, 6.87 (2s, 1H), 7.19-7.22 (m, 1H), 7.30-7.34 (m, 2H), 7.37-7.41 (m, 1H), 7.45-7.53 (m, 2H), 7.60-7.63 (m, 1H), 7.69-7.71 (m, 2H), 7.78-7.80 (m, 1H), 7.84-7.86 (m, 2H), 8.11 (s, 1H), 8.35 (s, 1H), 8.84 (s, 1H); HPLC (METHOD [A]): rt 12.26 min (100%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.26 min (100%)

Sources & evidence

ORD record
ord-88891cf81363460cb2a0eb783b4e91eb
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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