Ammonium Chloride → HCID 70874992, compound

HRID 2172257Notes

Reaction equation

HRID 2172257 reaction equation
CC(C)([O-])C.[Na+].Cl[C:8]1[N:9]([CH2:16][CH2:17][C@@H:18]([OH:48])[CH2:19][O:20][C:21]2[CH:47]=[CH:46][C:24]3[N:25]=[C:26]([N:28]4[CH2:33][CH2:32][N:31]([CH2:34][C:35]5[CH:40]=[CH:39][C:38]([O:41][C:42]([F:45])([F:44])[F:43])=[CH:37][CH:36]=5)[CH2:30][CH2:29]4)[S:27][C:23]=3[CH:22]=2)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[N:12]=1.[Cl-].[NH4+]>CS(C)=O>[N+:13]([C:11]1[N:12]=[C:8]2[N:9]([CH:10]=1)[CH2:16][CH2:17][C@H:18]([CH2:19][O:20][C:21]1[CH:47]=[CH:46][C:24]3[N:25]=[C:26]([N:28]4[CH2:33][CH2:32][N:31]([CH2:34][C:35]5[CH:40]=[CH:39][C:38]([O:41][C:42]([F:45])([F:44])[F:43])=[CH:37][CH:36]=5)[CH2:30][CH2:29]4)[S:27][C:23]=3[CH:22]=1)[O:48]2)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 70874661HCID 70874661, compound

Product 1

HCID 70874992HCID 70874992, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium tert-butoxide (112 mg) was added to a dimethylsulfoxide solution (6 ml) of (R)-4-(2-chloro-4-nitroimidazol-1-yl)-1-{2-[4-(4-trifluoromethoxybenzyl)piperazin-1-yl]benzothiazol-6-yloxy}butan-2-ol (662 mg), and the mixture was stirred at room temperature for 3 hours. 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 was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:1→ethyl acetate) to afford the title compound as a pale yellow powder (60 mg).

Workup

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

Sources & evidence

ORD record
ord-f689629e39284249810ef3b98d359dc1
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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