Diazald → HCID 53380261, compound

HRID 2388601Notes

Reaction equation

HRID 2388601 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][O: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][O: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 67386574HCID 67386574, compound

Product 1

HCID 53380261HCID 53380261, 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)-3-hydroxy-4-methyl-5-(4-morpholinophenyl)-1H-pyrrol-2(5H)-one (0.500 g, 1.28 mmol, 1 eq) and MeOH (10 ml), the product was purified by prep TLC using 4% methanol in chloroform as eluent; yield: 0.100 g (19.34%); MS m/z: 405.1 [M+H]+;1H-NMR: (400 MHz, DMSO-D6) δ: 12.37 (s, 1H), 8.13 (d, 1H), 7.68-7.64 (m, 1H), 7.50-7.48 (m, 1H), 7.38 (m, 1H), 7.25-7.22 (m, 1H), 7.08-7.06 (m, 2H), 6.82-6.80 (m, 2H), 5.68 (d, 1H), 3.93 (s, 3H), 3.66-3.63 (m, 4H), 3.17-3.01 (m, 4H), 1.66 (s, 3H); HPLC (METHOD [A]): rt 9.33 min (96.37%)

Workup

  1. customThe compound was synthesized
  2. customthe product was purified by prep TLC
  3. customrt 9.33 min (96.37%)

Sources & evidence

ORD record
ord-61bc869f3e234a48a15978f5033f5fa3
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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