Ammonium Hydroxide → HCID 178510752, compound

HRID 1043451Notes

Reaction equation

HRID 1043451 reaction equation
O1CCOCC1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([CH:26]3[CH2:31][CH2:30][CH:29]([CH2:32][C:33]#[N:34])[CH2:28][CH2:27]3)[NH:17][C:18]=2[C:19]2[C:20](F)=[N:21][CH:22]=[CH:23][CH:24]=2)=[C:10]([N+:35]([O-])=O)[CH:9]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[NH4+]>O>[F:7][C:8]1[CH:13]=[CH:12][C:11]2[C:14]3[N:15]=[C:16]([CH:26]4[CH2:31][CH2:30][CH:29]([CH2:32][C:33]#[N:34])[CH2:28][CH2:27]4)[NH:17][C:18]=3[C:19]3[CH:24]=[CH:23][CH:22]=[N:21][C:20]=3[NH:35][C:10]=2[CH:9]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 312751,4-DioxaneHCID 178510753HCID 178510753, compound

Product 1

HCID 178510752HCID 178510752, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 1,4-dioxane (1 mL) with 4-[4-(4-fluoro-2-nitrophenyl)-5-(2-fluoropyridin-3-yl)-1H-imidazol-2-yl]cyclohexylacetonitrile (0.17 g, 0.40 mmol) was added a solution of sodium dithionite (0.2 g, 0.001 mol) and ammonium hydroxide (0.4 mL, 0.003 mol) in water (1 mL), The reaction was stirred at 25° C. for 1 hour, concentrated, and was then extracted with isopropanol (3×1 mL each). The combined extracts were heated in a microwave reactor at 160° C. for 15 minutes, concentrated, and purified via column chromatography on silica gel (50% ethyl acetate 50% hexanes) to give 0.088 g of the desired product. 1H NMR (400 MHz, DMSO-d6): δ 8.42 (br s, 1H), 7.07 (m, 1H), 7.66 (m, 1H), 6.99 (m, 1H), 6.80-6.91 (m, 2H), 3.09 (m, 1H), 1.10-2.05 (m, 11H); MS [M+H]=374.0.

Workup

  1. concentrationconcentrated
  2. extractionwas then extracted with isopropanol (3×1 mL each)
  3. temperatureThe combined extracts were heated in a microwave reactor at 160° C. for 15 minutes
  4. concentrationconcentrated
  5. custompurified via column chromatography on silica gel (50% ethyl acetate 50% hexanes)

Sources & evidence

ORD record
ord-8cdfd227890b4a85b81e59beee65b193
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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