Sodium Carbonate → HCID 9930644, compound

HRID 746369Notes

Reaction equation

HRID 746369 reaction equation
C[C:2]1[C:7]([C:8]#[N:9])=[C:6]([S:10][CH2:11][CH:12]=O)[N:5]=[C:4]([CH3:14])[CH:3]=1.[O:15]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:19]=2[O:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClCCCl.CN(C=O)C>[O:15]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([N:25]3[CH2:30][CH2:29][N:28]([CH2:12][CH2:11][S:10][C:6]4[N:5]=[C:4]([CH3:14])[CH:3]=[CH:2][C:7]=4[C:8]#[N:9])[CH2:27][CH2:26]3)[C:19]=2[O:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 65853EltoprazineHCID 5049666Sodium triacetoxyborohydrideHCID 17953959HCID 17953959, compound

Product 1

HCID 9930644HCID 9930644, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

4,6-Dimethyl-2-(2-oxo-ethylsulfanyl)nicotinonitrile (2.9 g) was dissolved in 1,2-dichloroethane (150 mL), a solution of 4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazine (2.6 g) in DMF (150 mL) was added, followed by addition of sodium triacetoxyborohydride (14.9 g) and stirring for 2 h. The mixture was poured on water and Na2CO3 added until pH reached 7-8. The mixture was extracted with ethyl acetate, the combined organic phases dried and evaporated to give an oil which was subjected to purification by column chromatography (silica gel; ethyl acetate and heptane) giving an oil which precipitated as the oxalate salt (0.36 g) from acetone. LC/MS (m/z) 397 (MH+), RT=1.91, purity: 97%.

Workup

  1. additionadded until pH
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe combined organic phases dried
  4. customevaporated
  5. customto give an oil which
  6. customwas subjected to purification by column chromatography (silica gel; ethyl acetate and heptane)
  7. customgiving an oil which
  8. customprecipitated as the oxalate salt (0.36 g) from acetone
  9. customLC/MS (m/z) 397 (MH+), RT=1.91, purity: 97%

Sources & evidence

ORD record
ord-2012372a4ba14470831714445e2ab4ed
Source dataset
uspto-grants-2008_07
Patent number
US07393845B2

Reaction notes

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