Triethylamine → N-[2-(2-azabicyclo[2.2.2]oct-2-yl)quinolin-6-yl]-3-[6-(trifluoromethyl)pyridin-3-yl]propanamide

HRID 6802

Reaction equation

HRID 6802 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][N:2]2[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:19])[CH:15]=2)[N:10]=1.[F:20][C:21]([F:34])([F:33])[C:22]1[N:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](O)=[O:31])=[CH:24][CH:23]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH2:3][N:2]2[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:19][C:30](=[O:31])[CH2:29][CH2:28][C:25]3[CH:26]=[N:27][C:22]([C:21]([F:20])([F:33])[F:34])=[CH:23][CH:24]=3)[CH:15]=2)[N:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27833903-(6-(trifluoromethyl)pyridin-3-yl)propanoic AcidHCID 220189302-(2-Azabicyclo[2.2.2]oct-2-yl)quinolin-6-amine

Product 1

HCID 9955588N-[2-(2-azabicyclo[2.2.2]oct-2-yl)quinolin-6-yl]-3-[6-(trifluoromethyl)pyridin-3-yl]propanamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step B (307 mg, 1.2 mmol), the product of Step E (404 mg, 1.2 mmol) and triethylamine (0.17 mL, 1.2 mmol) in 10 mL methylene chloride was added 4-dimethylaminopyridine (222 mg, 1.8 mmol) followed by 1-(3-dimethylaminopropyl)3-ethylcarbodiimide HCl (349 mg, 1.82 mmol). The resulting mixture was stirred at r.t. for 3 days. The solvent was removed under vacuum and residue was purified by preparative thin layer chromatography eluting with hexane/ethyl acetate/triethylamine (1:7:0.1) to afford the product, MS: m/z 455 (MH+), as an off-white solid.

Workup

  1. customThe solvent was removed under vacuum and residue
  2. customwas purified by preparative thin layer chromatography
  3. washeluting with hexane/ethyl acetate/triethylamine (1:7:0.1)
  4. customto afford the product, MS

Sources & evidence

ORD record
ord-0c1bf5a8f124408fb10931da146f70b7
Source dataset
uspto-grants-2006_08
Patent number
US07084156B2

Linked notes

Loading…