Diazald → HCID 53380263, compound

HRID 1967622Notes

Reaction equation

HRID 1967622 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]([N: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:41]=[CH:42][C:43]([N:46]5[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]5)=[CH:44][CH: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 67386994HCID 67386994, compound

Product 1

HCID 53380263HCID 53380263, 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, 60 ml), 1-(1H-Benzo[d]imidazol-6-yl)-3-hydroxy-4-methyl-5-(4-(piperidin-1-yl)phenyl)-1H-pyrrol-2(5H)-one (0.700 g, 1.88 mmol, 1 eq) and MeOH (20 ml); yield: 0.050 g (7%); MS m/z: 403.1 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 8.59 (s, 1H), 7.81 (s, 1H), 7.55-7.53 (m, 1H), 7.45-7.42 (m, 1H), 7.06-7.04 (m, 2H), 6.82-6.79 (m, 2H), 5.69 (s, 1H), 3.93 (s, 3H), 3.05-3.02 (m, 4H), 1.70 (s, 3H), 1.53-1.46 (m, 6H); HPLC (METHOD [A]): rt 6.03 min (99.04%)

Workup

  1. customThe compound was synthesized
  2. customrt 6.03 min (99.04%)

Sources & evidence

ORD record
ord-6518125ea6f44279810eafde428efcd5
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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