Hydrochloric Acid → HCID 44553894, compound

HRID 1254059Notes

Reaction equation

HRID 1254059 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH3:31])([CH3:30])[C:28]#[N:29])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.Cl.CC[OH:35]>[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:22]=[CH:23][C:24]([C:27]([CH3:31])([CH3:30])[C:28]([NH2:29])=[O:35])=[CH:25][CH:26]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 44553895HCID 44553895, compound

Product 1

HCID 44553894HCID 44553894, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-(4-{5-[(4-chlorophenyl)thio]-1-methyl-2-phenyl-1H-imidazol-4-yl}phenyl)-2-methylpropanenitrile (Example 76, 120 mg, 0.270 mmol) in 3 mL of EtOH and 2 mL of 2 N NaOH was stirred at 90° C. over two days. The mixture was neutralized with 2 N HCl (pH=ca 5) and the product was extracted with EtOAc. The extracts were concentrated to dryness, and the residue was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, (CD3OD): 7.88 (d, 2H), 7.74 (m, 2H), 7.58 (m, 3H), 7.44 (d, 2H), 7.26 (d, 2H), 7.31 (d, 2H), 3.64 (s, 3H), 1.58 (s, 6H). LCMS: m/z 462 (M+H)+.

Workup

  1. extractionthe product was extracted with EtOAc
  2. concentrationThe extracts were concentrated to dryness
  3. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4834c010376a4fcc861697725fb7e360
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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