Triethylamine → HCID 178456931, compound

HRID 1620613Notes

Reaction equation

HRID 1620613 reaction equation
C(N(CC)CC)C.[CH:8]([C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=1)=O.Cl.Cl.[NH:24]1[CH2:29][CH2:28][CH:27](/[CH:30]=[C:31]2/[C:32]([NH:37][CH2:38][C:39]#[CH:40])=[N:33][C:34](=[O:36])[S:35]/2)[CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.O>[O:36]=[C:34]1[N:33]=[C:32]([NH:37][CH2:38][C:39]#[CH:40])/[C:31](=[CH:30]/[CH:27]2[CH2:26][CH2:25][N:24]([CH2:8][C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=3)[CH2:29][CH2:28]2)/[S:35]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 199588974-cyano-3-(trifluoromethyl)benzaldehydeHCID 178456897HCID 178456897, compound

Product 1

HCID 178456931HCID 178456931, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of triethylamine (1.38 mL) and 4-formyl-2-(trifluoromethyl)benzonitrile (593 mg) in DMF (10 mL) was added (5Z)-5-(piperidin-4-ylmethylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one dihydrochloride (800 mg). The reaction mixture was stirred at room temperature for 1 hr, and sodium triacetoxyborohydride (2.1 g) was added. The reaction mixture was stirred at room temperature for 3 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (250 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-5126a03b89e9476c9ce6edc69033e881
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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