Diazald → HCID 53380361, compound

HRID 2388608Notes

Reaction equation

HRID 2388608 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]([CH:46]5[CH2:51][CH2:50][CH:49]([N:52]6[CH2:57][CH2:56][O:55][CH2:54][CH2:53]6)[CH2:48][CH2:47]5)=[CH:42][CH:41]=4)[C:38]([CH3:58])=[C:37]([OH:59])[C:36]3=[O:60])[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:45]=[CH:44][C:43]([CH:46]5[CH2:47][CH2:48][CH:49]([N:52]6[CH2:53][CH2:54][O:55][CH2:56][CH2:57]6)[CH2:50][CH2:51]5)=[CH:42][CH:41]=4)[C:38]([CH3:58])=[C:37]([O:59][CH3:3])[C:36]3=[O:60])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 67387227HCID 67387227, compound

Product 1

HCID 53380361HCID 53380361, 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-(4-morpholinocyclohexyl)phenyl)-1H-pyrrol-2(5H)-one (0.350 g, 0.74 mmol, 1 eq) and MeOH (10 ml); yield: 0.040 g (11%); MS m/z: 487.2 [M+H]+; 1H-NMR: (400 MHz, CDCl3) δ: 12.34 (s, 1H), 8.13 (d, 1H), 7.70 (d, 1H), 7.45 (d, 2H), 7.17 (d, 5H), 5.75 (s, 1H), 3.95 (s, 3H), 3.56 (d, 4H), 2.35 (d, 4H), 2.1 (d, 1H), 1.90 (d, 2H), 1.69 (d, 5H), 1.4 (d, 4H); HPLC (METHOD [A]): rt 7.84 min (98.72%)

Workup

  1. customThe compound was synthesized
  2. customrt 7.84 min (98.72%)

Sources & evidence

ORD record
ord-b220d48b1ff14410ad23c107bfa2f8b2
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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