Trifluoroacetic acid → HCID 67501139, compound

HRID 921564Notes

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

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, 93%) as a brown solid.

Workup

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

Sources & evidence

ORD record: ord-0eedb5b812f44adc96b494c0f65771cd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273045B2

Reaction notes

Loading…