HCID 68081530, compound → HCID 68081065, compound

HRID 1748188Notes

Reaction equation

HRID 1748188 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])[C:5]=2[CH2:16][O:17][CH:18]2[CH2:24][CH:23]3[N:25](C(OC(C)(C)C)=O)[CH:20]([CH2:21][CH2:22]3)[CH2:19]2)[CH2:3][CH2:2]1>FC(F)(F)C(O)=O.ClCCl>[CH:23]12[NH:25][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH:18]([O:17][CH2:16][C:5]1[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])=[N:7][O:8][C:4]=1[CH:1]1[CH2:2][CH2:3]1)[CH2:24]2

Participants

4

Reactant 1

HCID 68081530HCID 68081530, compound

Product 1

HCID 68081065HCID 68081065, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The previous amine, tert-Butyl 3-((5-cyclopropyl-3-(o-tolyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1.60 g, 3.65 mmol) was dissolved in trifluoroacetic acid in dichloromethane (30 mL, 20% solution) at RT. The solution was stirred for 1 hour at RT and the solvent was evaporated. The residue was dissolved in ethyl acetate (125 mL), washed with a saturated solution of sodium bicarbonate (100 mL), the organic layer was dried with magnesium sulfate and evaporated in vacuo. The crude residue was purified by silica gel chromatography using a gradient of 0-20% ethanol/dichloromethane to afford the desired product as a colorless oil. 1H-NMR (DMSO-d6, 400 MHz) δ 8.44 (bs, 1H), 7.43-7.34 (m, 2H), 7.32-7.28 (m, 2H), 4.21 (s, 2H), 3.83 (bs, 2H), 3.55 (t, J=4.0 Hz, 1H), 2.35-2.28 (m, 1H), 2.20 (s, 3Hc-1.70 (m, 8H), 1.16-1.06 (m, 4H). MS m/z 339.2 (M+1).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate (125 mL)
  3. washwashed with a saturated solution of sodium bicarbonate (100 mL)
  4. dry with materialthe organic layer was dried with magnesium sulfate
  5. customevaporated in vacuo
  6. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1b0eaf6c08a74165a97bd3170033456b
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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