Diazald → HCID 53380074, compound

HRID 2388597Notes

Reaction equation

HRID 2388597 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]([CH:48]([CH3:50])[CH3:49])=[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]([CH:48]([CH3:50])[CH3:49])=[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 67386804HCID 67386804, compound

Product 1

HCID 53380074HCID 53380074, 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 (1/7.5 v/v, 17 ml), 1-(1H-Benzo[d]imidazol-6-yl)-5-(2,3-difluorophenyl)-4-isopropyl-3-hydroxy-1H-pyrrol-2(5H)-one (0.15 g, 0.34 mmol, 1 eq) and MeOH (10 ml), the product was further purified by prep TLC; yield: 0.040 g (10.4%); MS m/z: 384.1 [M+H]+;1H-NMR: (400 MHz, CDCl3) δ: 7.88 (s, 1H), 7.80 (bs, 1H), 7.52 (bs, 1H), 7.2-6.88 (m, 4H), 6.0 (s, 1H), 4.08 (s, 3H), 2.61 (bs, 1H), 1.1-1.04 (m, 6H); HPLC (METHOD [A]): rt 14.51 min (96.9%)

Workup

  1. customThe compound was synthesized
  2. customthe product was further purified by prep TLC
  3. customrt 14.51 min (96.9%)

Sources & evidence

ORD record
ord-14251cd9e62b4c7ca8ce591c08d3aaa1
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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