Ammonium Chloride → HCID 86709397, compound

HRID 2172256Notes

Reaction equation

HRID 2172256 reaction equation
CC(C)([O-])C.[Na+].Cl[C:8]1[N:9]([CH2:16][CH2:17][CH:18]([OH:48])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][CH:30]([CH2:33][C:34]4[O:35][C:36]5[CH:42]=[CH:41][C:40]([O:43][C:44]([F:47])([F:46])[F:45])=[CH:39][C:37]=5[CH:38]=4)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[N:12]=1.[Cl-].[NH4+]>CN1CCCC1=O>[N+:13]([C:11]1[N:12]=[C:8]2[N:9]([CH:10]=1)[CH2:16][CH2:17][CH:18]([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][CH:30]([CH2:33][C:34]4[O:35][C:36]5[CH:42]=[CH:41][C:40]([O:43][C:44]([F:47])([F:46])[F:45])=[CH:39][C:37]=5[CH:38]=4)[CH2:29][CH2:28]3)=[CH:23][CH:22]=1)[O:48]2)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 70874524HCID 70874524, compound

Product 1

HCID 86709397HCID 86709397, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Sodium tert-butoxide (81 mg) was added to an N-methylpyrrolidone solution (5 ml) of 4-(2-chloro-4-nitroimidazol-1-yl)-1-{4-[4-(5-trifluoromethoxybenzofuran-2-ylmethyl)piperidin-1-yl]phenoxy}butan-2-ol (469 mg), and the mixture was stirred at room temperature for 1 hour. A saturated ammonium chloride aqueous solution was added to the reaction mixture, and precipitated solid was sequentially washed with water and diisopropyl ether. The crude product formed was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1→3:1) to afford the title compound as a white powder (181 mg).

Workup

  1. customprecipitated solid
  2. washwas sequentially washed with water and diisopropyl ether
  3. customThe crude product formed
  4. customwas purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1→3:1)

Sources & evidence

ORD record
ord-2ff43dd6b8ad4f0db0395f28db5f8488
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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