Diazald → HCID 53379985, compound

HRID 1967610Notes

Reaction equation

HRID 1967610 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]=[CH:32][C:33]([N:35]3[CH:39]([C:40]4[CH:45]=[C:44]([Br:46])[CH:43]=[CH:42][C:41]=4[F:47])[C:38]([CH3:48])=[C:37]([OH:49])[C:36]3=[O:50])=[CH:34][C:29]=2[N:28]=[CH:27]1>CO>[NH:28]1[C:29]2[CH:34]=[C:33]([N:35]3[CH:39]([C:40]4[CH:45]=[C:44]([Br:46])[CH:43]=[CH:42][C:41]=4[F:47])[C:38]([CH3:48])=[C:37]([O:49][CH3:3])[C:36]3=[O:50])[CH:32]=[CH:31][C:30]=2[N:26]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 178431714HCID 178431714, compound

Product 1

HCID 53379985HCID 53379985, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound was synthesized starting from KOH (15 g, 267.8 mmol in water), diazald (20 g, 93.37 mmol, 5 eq), ethylene glycol/Et2O (2/1 v/v, 140 mL) 1-(1H-benzo[d]imidazol-5-yl)-5-(5-bromo-2-fluorophenyl)-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (2 g, 5.57 mmol, 1 eq) and MeOH (50 mL); yield: 1.3 g (57.2%); MS m/z: 416.3 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 1.76 (s, 3H), 3.95 (s, 3H), 6.00 (s, 1H), 7.13 (m, 1.3H), 7.25-7.27 (m, 1.6 H), 7.47-7.49 (m, 1.6H), 7.47-7.52 (m, 1.5 H), 7.65 (m, 1.5H), 8.15 (s, 1H); HPLC (METHOD [A]): rt 12.55 min (98.5%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.55 min (98.5%)

Sources & evidence

ORD record
ord-b82be393dcef4697878cec3ecc2c1cd1
Source dataset
uspto-grants-2013_04
Patent number
US08420828B2

Reaction notes

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