tert-Butyl ((1R,3S)-3-Isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)carbamate → (1R,3S)-3-Isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentanamine

HRID 969580Notes

Reaction equation

HRID 969580 reaction equation
[CH:1]([C@:4]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[N:25]=[CH:24][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:22][C:21]=3[CH2:20]2)=[O:18])[CH2:8][CH2:7][C@@H:6]([NH:9]C(=O)OC(C)(C)C)[CH2:5]1)([CH3:3])[CH3:2]>Cl.O1CCOCC1>[CH:1]([C@:4]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[N:25]=[CH:24][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:22][C:21]=3[CH2:20]2)=[O:18])[CH2:8][CH2:7][C@@H:6]([NH2:9])[CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 60122330tert-Butyl ((1R,3S)-3-Isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)carbamate

Product 1

HCID 60122294(1R,3S)-3-Isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentanamineYield 117.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl ((1R,3S)-3-isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)carbamate (300 mg, 0.6 mmol) was dissolved in a 4 M solution of HCl in 1,4-dioxane (20 mL). After being stirred at room temperature for 2 hrs, the solution was concentrated. The residue was treated with ether to give 250 mg of yellow solid. MS calculated for C18H24F3N3O: (M+H)+356; found 356.1.

Workup

  1. concentrationthe solution was concentrated
  2. additionThe residue was treated with ether

Sources & evidence

ORD record
ord-5795720565de4b9291849d6591fb2044
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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