Sodium Bicarbonate → HCID 178459307, compound

HRID 1620542Notes

Reaction equation

HRID 1620542 reaction equation
Cl.Cl.[OH:3][C:4]([CH3:21])([CH3:20])[CH2:5][NH:6][C:7]1=[N:8][C:9](=[O:19])[S:10]/[C:11]/1=[CH:12]\[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>CN(C=O)C.C(N(CC)CC)C>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:16]2[CH2:17][CH2:18][CH:13](/[CH:12]=[C:11]3/[C:7]([NH:6][CH2:5][C:4]([OH:3])([CH3:21])[CH3:20])=[N:8][C:9](=[O:19])[S:10]/3)[CH2:14][CH2:15]2)=[C:25]([C:31]([F:32])([F:33])[F:34])[CH:24]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 27790174-Chloro-2-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178459303HCID 178459303, compound

Product 1

HCID 178459307HCID 178459307, compoundYield 30.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of (5Z)-4-[(2-hydroxy-2-methylpropyl)amino]-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (200 mg) in DMF (2 mL) was added a solution of triethylamine (0.32 mL) and 4-chloro-2-(trifluoromethyl)benzaldehyde (117 mg) in DMF (1 mL). The reaction mixture was stirred at room temperature for 1 hr, and sodium triacetoxyborohydride (501 mg) was added. The reaction mixture was stirred at room temperature overnight, saturated aqueous sodium hydrogen carbonate solution 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 (82 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  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-7108e499e25045ada9f9500c4e86e907
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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