Tert-butyl 3-[5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate → 7-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

HRID 394182Notes

Reaction equation

HRID 394182 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:18]=[C:17]([C:19]2[CH2:25][CH:24]3[N:26](C(OC(C)(C)C)=O)[CH:21]([CH2:22][CH2:23]3)[CH:20]=2)[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13](=[O:42])[N:14]2[C:34]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=1[Cl:41]>FC(F)(F)C(O)=O>[CH:21]12[NH:26][CH:24]([CH2:23][CH2:22]1)[CH2:25][C:19]([C:17]1[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][C:13](=[O:42])[N:14]3[C:34]3[C:35]([Cl:41])=[CH:36][CH:37]=[CH:38][C:39]=3[Cl:40])=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[Cl:1])[N:18]=1)=[CH:20]2

Participants

3

Reactant 1

HCID 22648108Tert-butyl 3-[5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

Product 1

HCID 226479477-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl 3-[5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (103 mg) was dissolved in 1 mL of trifluoroacetic acid and stirred under nitrogen at rt for 0.75 h. The resulting reaction mixture was concentrated under reduced pressure and purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in methanol to yield 7-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one. Mass spectrum (ESI) 526 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. custompurified by preparative thin-layer chromatography
  4. washeluting with 95:5 CH2Cl2-2M NH3 in methanol

Sources & evidence

ORD record
ord-5306de9372704ee4a4744f0163d6bb07
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

Loading…