Water → HCID 59517316, compound

HRID 2079124Notes

Reaction equation

HRID 2079124 reaction equation
[NH4+]=[S:2].[Si:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:31]=[C:30]([CH3:32])[O:29][N:28]=3)=[CH:23][CH:22]=2)[C:18]#[N:19])=[CH:13][C:12]=1[O:33][CH3:34])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].C1COCC1.O>CO.C(OCC)(=O)C>[Si:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[N:31]=[C:30]([CH3:32])[O:29][N:28]=3)=[CH:25][CH:26]=2)[C:18]([NH2:19])=[S:2])=[CH:13][C:12]=1[O:33][CH3:34])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 59516853HCID 59516853, compound

Product 1

HCID 59517316HCID 59517316, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 32 ml of a 20% aqueous solution of ammonium sulfide to a solution of 8.45 g of (4-t-butyldimethylsilanyloxy-3-methoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile in 300 ml of a methanol:THF=2:1 mixed solvent, the mixture was stirred at room temperature for 23 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. After washing the organic layer with saturated brine, it was dried over anhydrous sodium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (8.26 g) as a crude product.

Workup

  1. washAfter washing the organic layer with saturated brine, it
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2fc2b337ffb344418cc640bd944fda48
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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