Diazald → HCID 53380358, compound

HRID 2388607Notes

Reaction equation

HRID 2388607 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][C:49]([F:53])([F:52])[CH2:48][CH2:47]5)=[CH:42][CH:41]=4)[C:38]([CH3:54])=[C:37]([OH:55])[C:36]3=[O:56])[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:41]=[CH:42][C:43]([CH:46]5[CH2:51][CH2:50][C:49]([F:53])([F:52])[CH2:48][CH2:47]5)=[CH:44][CH:45]=4)[C:38]([CH3:54])=[C:37]([O:55][CH3:3])[C:36]3=[O:56])[CH:33]=[CH:34][C:29]=2[N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 67387244HCID 67387244, compound

Product 1

HCID 53380358HCID 53380358, 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 (1/2.5 v/v, 28 ml), 1-(1H-Benzo[d]imidazol-6-yl)-5-(4-(4,4-difluorocyclohexyl)-phenyl)-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (0.800 g, 1.88 mmol, 1 eq) and MeOH (10 ml); yield: 0.060 g (7.3%); MS m/z: 438.3 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 12.39 (s, 1H), 8.14 (d, 1H), 7.69 (d, 1H), 7.49 (d, 1H), 7.26-7.15 (m, 4H), 5.79 (s, 1H), 3.93 (s, 3H), 2.67-2.54 (m, 1H), 2.03-1.88 (m, 3H), 1.83-1.76 (m, 3H), 1.69 (s, 3H), 1.59-1.50 (m, 2H); HPLC (METHOD [A]): rt 14.64 min (95.14%)

Workup

  1. customThe compound was synthesized
  2. customrt 14.64 min (95.14%)

Sources & evidence

ORD record
ord-a0c071e6d12a44e6883955d2a38560c4
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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