Diazald → HCID 53380073, compound

HRID 2388596Notes

Reaction equation

HRID 2388596 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][CH:43]=[C:42]([F:46])[C:41]=4[F:47])[C:38]([CH2:48][CH2:49][CH3:50])=[C:37]([OH:51])[C:36]3=[O:52])[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][CH:43]=[C:42]([F:46])[C:41]=4[F:47])[C:38]([CH2:48][CH2:49][CH3:50])=[C:37]([O:51][CH3:3])[C:36]3=[O:52])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 67387420HCID 67387420, compound

Product 1

HCID 53380073HCID 53380073, 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 (1/3 v/v, 40 ml), 1-(1H-Benzo[d]imidazol-6-yl)-5-(2,3-difluorophenyl)-3-hydroxy-4-propyl-1H-pyrrol-2(5H)-one (1.0 g, 2.71 mmol, 1 eq) and MeOH (10 ml), the product was further purified by preparative HPLC; yield: 0.120 g (11.6%); MS m/z: 384.1 [M+H]+; 1H-NMR: (400 MHz, CDCl3) δ: 0.96 (t, 3H), 1.6-1.4 (m, 6H), 1.94-1.87 (m, 1H), 2.47-2.39 (m, 1H), 4.08 (s, 3H), 5.90 (bs, 1H), 6.92(bs, 1H), 7.03-6.94 (m,2H), 7.54 (bs, 1H), 7.83 (s, 1H), 7.94 (s, 1H); HPLC (METHOD [A]): rt 14.38 min (100%)

Workup

  1. customThe compound was synthesized
  2. customthe product was further purified by preparative HPLC
  3. customrt 14.38 min (100%)

Sources & evidence

ORD record
ord-8629d32467714131ae4ab2837517bc0f
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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