Trifluoroacetic acid → HCID 89922503, compound

HRID 921948Notes

Reaction equation

HRID 921948 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

HCID 6422Trifluoroacetic acidHCID 131734957HCID 131734957, compound

Product 1

HCID 89922503HCID 89922503, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customSolvent was evaporated
  2. additionthe residue was diluted with dichloromethane
  3. washwashed with saturated sodium bicarbonate
  4. extractionThe aqueous layer was extracted with dichloromethane two more times
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe crude product was purified by flash chromatography on silica gel using
  9. washan automated ISCO system (24 g gold column, eluting with 0-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b290bd4ec0b346e9a154445703edf776
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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