Diazald → HCID 53380363, compound

HRID 1967628Notes

Reaction equation

HRID 1967628 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][N:43]([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[CH2:42][CH2:41]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]([CH:40]4[CH2:45][CH2:44][N:43]([C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)[CH2:42][CH2:41]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 67387537HCID 67387537, compound

Product 1

HCID 53380363HCID 53380363, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound was synthesized starting from KOH (15 eq in water), diazald (9 eq), ethylene glycol/Et2O (1/5 v/v, 18 ml), 1-(1H-Benzo[d]imidazol-6-yl)-3-hydroxy-4-methyl-5-(1-phenylpiperidin-4-yl)-1H-pyrrol-2(5H)-one (0.280 g, 0.72 mmol, 1 eq) and MeOH (15 ml), the product was further purified by prep TLC; yield: 0.021 g (5.2%); MS m/z: 403.1 [M+H]+; 1H-NMR: (400 MHz, CDCl3) δ: 7.95 (s, 1H), 7.65-7.60 (m, 1H), 7.17 (m, 3H), 6.80 (d, 1H), 4.52 (s, 1H), 4.03 (s, 3H), 3.69-3.66 (m, 3H), 2.54-2.41 (m, 3H), 2.05 (s, 4H), 1.88 (m, 5H), 1.41-1.25 (m, 2H); HPLC (METHOD [A]): rt 6.05 min (88.89%)

Workup

  1. customThe compound was synthesized
  2. customthe product was further purified by prep TLC
  3. customrt 6.05 min (88.89%)

Sources & evidence

ORD record
ord-87401ca30b4249dc8f574303045b8a9b
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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