Trifluoroacetic acid → HCID 90066696, compound

HRID 1487961Notes

Reaction equation

HRID 1487961 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:29])=[CH:7][C:8]([CH3:28])=[C:9]([C:11]2[NH:27][C:14]3[CH2:15][CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19][C:13]=3[N:12]=2)[CH:10]=1)=[O:4].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH:12]1[C:13]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15][C:14]=2[N:27]=[C:11]1[C:9]1[C:8]([CH3:28])=[CH:7][C:6]([CH3:29])=[C:5]([CH:10]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90066697tert-butyl 2-(5-(methoxycarbonyl)-2,4-dimethylphenyl)-4,5,7,8-tetrahydroimidazo[4,5-d]azepine-6(1H)-carboxylate2×

Product 1

HCID 90066696HCID 90066696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of tert-butyl 2-(5-(methoxycarbonyl)-2,4-dimethylphenyl)-4,5,7,8-tetrahydroimidazo[4,5-d]azepine-6(1H)-carboxylate (compound 83.3, 800 mg, 2.00 mmol) in dichloromethane (16 mL). Trifluoroacetic acid (4 mL) was added drop-wise and the resulting solution was stirred for 5 h at room temperature. The pH of the solution was carefully adjusted to 8-9 with NaHCO3 (sat.) and the aqueous phase was extracted with DCM (3×30 mL), and the combined organics were dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 0.60 mg (crude) of the title compound as brown oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. extractionthe aqueous phase was extracted with DCM (3×30 mL)
  3. dry with materialthe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a52fd320088f4b1db8f0621608206865
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

Loading…