Trifluoroacetic acid → HCID 89922503, compound
Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[C:10]([N:16]2[CH2:28][CH2:27][C:19]3([CH2:23][N:22]([C:24](=[O:26])[CH3:25])[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)[C:9]=1[Cl:29])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:24]([N:22]1[CH2:21][CH2:20][C:19]2([CH2:18][CH2:17][N:16]([C:10]3[CH:11]=[C:12]([CH:13]=[C:8]([NH2:7])[C:9]=3[Cl:29])[C:14]#[N:15])[CH2:28][CH2:27]2)[CH2:23]1)(=[O:26])[CH3:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-butyl(3-(2-acetyl-2,8-diazaspiro[4.5]decan-8-yl)-2-chloro-5-cyanophenyl)carbamate (100 mg, 0.231 mmol) in DCM (2 mL) was treated with TFA (0.338 mL, 4.39 mmol) at room temperature for 2 h. Solvent was evaporated and the residue was diluted with dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane two more times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, the crude product was purified by flash chromatography on silica gel using an automated ISCO system (24 g gold column, eluting with 0-5% methanol/dichloromethane). 3-(2-acetyl-2,8-diazaspiro[4.5]decan-8-yl)-5-amino-4-chlorobenzonitrile (70 mg) was obtained as a light yellow oil.