Trifluoroacetic acid → HCID 67501139, compound

HRID 1625252Notes

Reaction equation

HRID 1625252 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18]([Cl:19])=[C:13]2[C:12]([CH:20]([CH3:22])[CH3:21])=[N:11]1)[C:5]#[N:6].C(O[BH-](O[C:33](=O)[CH3:34])OC(=O)C)(=O)C.[Na+].F[C:38](F)(F)C(O)=O.O.C(=O)(O)[O-].[Na+]>ClCCl.CC(C)=O>[Cl:19][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[N:10]([C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[NH:1][CH:33]([CH3:34])[CH3:38])[N:11]=[C:12]([CH:20]([CH3:22])[CH3:21])[C:13]=12

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 67501755HCID 67501755, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 67501139HCID 67501139, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound (107a) (0.100 g) and sodium triacetoxyborohydride (0.130 g) were suspended in dichloromethane (1.6 mL), and trifluoroacetic acid (0.3 mL) and acetone (0.050 mL) were added to the resulting suspension at 0° C., followed by stirring at 0° C. for 20 min. Saturated sodium bicarbonate water was added to the reaction solution, and the organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and the solvent was distilled away. Methanol and water were added to the residue, and the precipitate was collected by filtration and dried under reduced pressure to obtain compound (120a) (0.100 g, 930) as a brown solid.

Workup

  1. washthe organic layer was washed with saturated saline
  2. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled away
  4. additionMethanol and water were added to the residue
  5. filtrationthe precipitate was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-224b9d7bd81f4aca86e9f1a3f23c5af4
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

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