1,2-Dichloroethane → HCID 89709467, compound

HRID 1479182Notes

Reaction equation

HRID 1479182 reaction equation
[CH:1]1([CH:7]2[CH:16]3[CH2:17][CH2:18][CH2:19][O:20][CH:15]3[C:14]3[CH:13]=[C:12]([C:21]([OH:23])=[O:22])[CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(N)CC1.CCN(C(C)C)C(C)C.C(Cl)CCl>C(Cl)Cl>[CH:1]1([C@H:7]2[C@@H:16]3[CH2:17][CH2:18][CH2:19][O:20][C@@H:15]3[C:14]3[CH:13]=[C:12]([C:21]([OH:23])=[O:22])[CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 89709503HCID 89709503, compound

Product 1

HCID 89709467HCID 89709467, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4aSR*,5SR*,10bSR*)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-9-carboxylic acid (50 mg, 0.16 mmol, 1 equiv.) in dry CH2Cl2 (1.6 mL) under argon atmosphere at 0° C. was added cyclopropanamine (12.1 μL, 0.17 mmol, 1.1 equiv.) followed by DIPEA (41 μL, 0.24 mmol, 1.5 equiv.) and EDC (33.5 mg, 0.17 mmol, 1.1 equiv). The reaction mixture was allowed to reach r.t. and stirred overnight. The solvent was removed under reduced pressure and the residue directly purified by Combiflash chromatography (SiO2, c-Hexane/AcOEt) to afford (4aS,5S,10bS)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-9-carboxylic acid (10 mg, 17%). The compound was prepared as hydrochloride salt following the method described in example 1.

Workup

  1. customto reach r.t.
  2. customThe solvent was removed under reduced pressure
  3. customthe residue directly purified by Combiflash chromatography (SiO2, c-Hexane/AcOEt)

Sources & evidence

ORD record
ord-bd8409221243476ea981914aca211e75
Source dataset
uspto-grants-2016_08
Patent number
US09408842B2

Reaction notes

Loading…