Diazald → HCID 53379980, compound

HRID 1967606Notes

Reaction equation

HRID 1967606 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][CH2:43][CH2:42][CH2:41]4)[C:38]([CH3:46])=[C:37]([OH:47])[C:36]3=[O:48])[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[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]4)[C:38]([CH3:46])=[C:37]([O:47][CH3:3])[C:36]3=[O:48])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 67387260HCID 67387260, compound

Product 1

HCID 53379980HCID 53379980, 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-cyclohexyl-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (1.00 g, 3.22 mmol, 1 eq) and MeOH (10 ml); yield: 0.250 g (25%); MS m/z: 326.1 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 1.05 (d, 3H), 1.40 (d, 2H), 1.65-1.60 (m, 4H), 2.05 (s, 3H), 4.03 (s, 3H), 4.40 (s, 1H), 7.05 (s, 1H), 7.62 (s, 1H), 7.63 (s, 1H), 7.82 (s, 1H); HPLC (METHOD [A]): rt 11.25 min (98.78%)

Workup

  1. customThe compound was synthesized
  2. customrt 11.25 min (98.78%)

Sources & evidence

ORD record
ord-02647d4103dc4567bfe855006b9e0df7
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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