Diazald → HCID 53380266, compound

HRID 2388606Notes

Reaction equation

HRID 2388606 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][C:43]([CH:46]5[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]5)=[CH:42][CH:41]=4)[C:38]([CH3:52])=[C:37]([OH:53])[C:36]3=[O:54])[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][C:43]([CH:46]5[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]5)=[CH:42][CH:41]=4)[C:38]([CH3:52])=[C:37]([O:53][CH3:3])[C:36]3=[O:54])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 67387564HCID 67387564, compound

Product 1

HCID 53380266HCID 53380266, 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 v/v, 30 ml), 1-(1H-Benzo[d]imidazol-6-yl)-5-(4-cyclohexylphenyl)-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (0.900 g, 2.32 mmol, 1 eq) and MeOH (10 ml); yield: 0.200 g (21.4%); MS m/z: 402.1 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 12.4 (b, 1H), 8.32 (s, 1H), 7.71 (s, 1H), 7.46-7.44 (m, 1H), 7.34 (m, 1H), 7.16-7.11 (m, 4H), 5.77 (s, 1H), 3.93 (s, 3H), 2.39 (m, 1H), 1.79-1.60 (m, 8H), 1.40-1.20 (m, 6H); HPLC (METHOD [A]): rt 15.68 min (96.92%)

Workup

  1. customThe compound was synthesized
  2. customrt 15.68 min (96.92%)

Sources & evidence

ORD record
ord-3a18726f1100445e9d925c94cadd725b
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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