Diazald → HCID 53380454, compound

HRID 2388611Notes

Reaction equation

HRID 2388611 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]([CH:40]4[CH2:45][CH2:44][CH:43]([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[CH2:42][CH2:41]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]([CH:40]4[CH2:41][CH2:42][CH:43]([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[CH2:44][CH2:45]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 67387509HCID 67387509, compound

Product 1

HCID 53380454HCID 53380454, 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, 60 ml), 1-(1H-Benzo[d]imidazol-6-yl)-3-hydroxy-4-methyl-5-(4-phenylcyclohexyl)-1H-pyrrol-2(5H)-one (1.0 g, 2.58 mmol, 1 eq) and MeOH (20 ml); yield: 0.100 g (10%); MS m/z: 402.2 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 12.53 (s, 1H), 8.32 (s, 1H), 7.64 (m, 2H), 7.25-7.08 (m, 7H), 4.81 (s, 1H), 3.87 (s, 3H), 2.20-2.20 (m, 2H), 2.01 (s, 3H), 1.78-1.4 (m, 5H), 1.37-1.14 (m, 7H); HPLC (METHOD [A]): rt 14.80 min (96.02%)

Workup

  1. customThe compound was synthesized
  2. customrt 14.80 min (96.02%)

Sources & evidence

ORD record
ord-8409c16ad1c34b8caa7b95d22ffdf0c2
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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