Acetone → HCID 86700756, compound

HRID 2272548Notes

Reaction equation

HRID 2272548 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[N:24]1[C:32]2[C:27](=[C:28]([N:33]3[CH:37]=[C:36]([C:38]4[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=4)[N:35]=[CH:34]3)[CH:29]=[CH:30][CH:31]=2)[C:26]([CH:44]([CH3:46])[CH3:45])=[N:25]1)[C:19]#[N:20].FC(F)(F)C(O)=O.[CH3:54][C:55]([CH3:57])=O>ClCCl>[CH:44]([C:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][C:28]=2[N:33]2[CH:37]=[C:36]([C:38]3[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=3)[N:35]=[CH:34]2)[N:24]([C:23]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=2[NH:15][CH:55]([CH3:57])[CH3:54])[N:25]=1)([CH3:46])[CH3:45]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 86700755HCID 86700755, compound

Product 1

HCID 86700756HCID 86700756, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Sodium triacetoxyborohydride (192 mg) was added to a solution of compound (10b) (190 mg) in dichloromethane (2.7 mL), and the mixture was cooled to 0° C. Then trifluoroacetic acid (0.45 mL) and acetone (67 μL) were added thereto and the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, the reaction solution was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine and dried by the addition of anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (10c) (208.6 mg, yield 990) as a white foamy substance.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solution was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried by the addition of anhydrous sodium sulfate
  5. customAfter removal of the solvent
  6. customby evaporation
  7. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-513ff57bb19c4bbaa154e08518df032a
Source dataset
uspto-grants-2015_09
Patent number
US09120780B2

Reaction notes

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