Diazald → HCID 53380264, compound

HRID 1967623Notes

Reaction equation

HRID 1967623 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]([O:46][CH:47]5[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]5)=[CH:42][CH:41]=4)[C:38]([CH3:53])=[C:37]([OH:54])[C:36]3=[O:55])[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:41]=[CH:42][C:43]([O:46][CH:47]5[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]5)=[CH:44][CH:45]=4)[C:38]([CH3:53])=[C:37]([O:54][CH3:3])[C:36]3=[O:55])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 67387738HCID 67387738, compound

Product 1

HCID 53380264HCID 53380264, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound was synthesized starting from KOH (15 eq in water), diazald (8 eq), ethylene glycol/Et2O (1/2 v/v, 30 ml), 1-(1H-Benzo[d]imidazol-6-yl)-5-(4-(cyclohexyloxy)phenyl)-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (0.500 g, 1.24 mmol, 1 eq) and MeOH (10 ml); yield: 0.050 g (10%); MS m/z: 418.2 [M+H]+; 1H-NMR: (400 MHz, CDCl3) δ: 7.90 (s, 1H), 7.78 (s, 1H), 7.5 (s, 1H), 7.26 (s, 2H), 7.06 (d, 2H), 6.76 (d, 2H), 5.24 (s, 1H), 4.07 (d, 4H), 1.80 (d, 2H), 1.76 (d, 5H), 1.45 (d, 3H), 1.30 (d, 4H); HPLC (METHOD [A]): rt 15.23 min (100%)

Workup

  1. customThe compound was synthesized
  2. customrt 15.23 min (100%)

Sources & evidence

ORD record
ord-cf0a836dca08464081884ad59b17bdf5
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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