Ammonium Hydroxide → HCID 178441585, compound

HRID 75190Notes

Reaction equation

HRID 75190 reaction equation
[C:1]([C:5]1[NH:6][C:7]([C:20]2[C:21]([F:26])=[N:22][CH:23]=[CH:24][CH:25]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[N+:17]([O-])=O)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[NH4+]>O1CCOCC1.O>[C:1]([C:5]1[NH:6][C:7]([C:20]2[C:21]([F:26])=[N:22][CH:23]=[CH:24][CH:25]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[NH2:17])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 1784415863-[2-tert-butyl-4-(4-fluoro-2-nitrophenyl)-1H-imidazol-5-yl]-2-fluoropyridine

Product 1

HCID 178441585HCID 178441585, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-[2-tert-butyl-4-(4-fluoro-2-nitrophenyl)-1H-imidazol-5-yl]-2-fluoropyridine (0.13 g, 0.36 mmol) in 1,4-dioxane (4 mL) was added a solution of sodium dithionite (0.5 g, 0.003 mol) and ammonium hydroxide (0.5 mL, 0.004 mol) in water (4 mL). The reaction was stirred at 25° C. for 4 h and was then extracted with EtOAc. The combined extracts were washed with water 2×, dried over MgSO4 and concentrated in vacuo to give 0.098 g of the desired product. 1H NMR (500 MHz, CD3OD): δ 8.28-8.29 (m, 1H), 7.95-7.99 (m, 1H), 7.45-7.46 (m, 1H), 7.34-7.35 (m, 1H), 6.77-7.11 (m, 2H), 6.73-6.77 (m, 1H), 1.56 (s, 9H). MS [M+H]=329.0.

Workup

  1. extractionwas then extracted with EtOAc
  2. washThe combined extracts were washed with water 2×
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58ad683794524b7a90d1608d73c3c732
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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