1,2-Dichloroethane → N-{[3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylcarbamoyl]-methyl}-nicotinamide

HRID 352252Notes

Reaction equation

HRID 352252 reaction equation
I.[NH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([N:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:19])[C:13]=3[C:12]3=[N:20][O:21][C:22]([CH3:23])=[C:11]3[C:10]2=[O:24])[CH2:4]1.C(Cl)CCl.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH:48]1[CH:53]=[N:52][CH:51]=[C:50]([C:54]([NH:56][CH2:57][C:58](O)=[O:59])=[O:55])[CH:49]=1>CN(C=O)C>[Cl:19][C:14]1[C:13]2[C:12]3[C:11](=[C:22]([CH3:23])[O:21][N:20]=3)[C:10](=[O:24])[N:9]([CH:5]3[CH2:6][CH2:7][CH2:8][CH:3]([NH:2][C:58]([CH2:57][NH:56][C:54](=[O:55])[C:50]4[CH:49]=[CH:48][CH:53]=[N:52][CH:51]=4)=[O:59])[CH2:4]3)[C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 68499Nicotinuric AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 227137135-(3-Aminocyclohexyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

Product 1

HCID 22713922N-{[3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylcarbamoyl]-methyl}-nicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3-Amino-cyclohexyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin4-one hydroiodide (70 mg, 0.19 mmol) was combined with EDC (47 mg, 0.25 mmol), 1-hydroxy-7-azabenzo-triazole (34 mg, 0.25 mmol), N,N-diisopropylethyl amine (0.10 mL, 0.58 mmol), (5 mg, cat.), and nicotinuric acid (44 mg, 0.24 mmol) in DMF(6 mL) and the mixture stirred overnight at rt. The mixture was then concentrated in vacuo and the residue taken up in water and extracted with EtOAc. The combined extracts were dried over Na2SO4 and concentrated in vacuo. The residue was loaded onto a silica gel column and eluted with MeOH/CH2Cl2 which allowed for the recovery of 87 mg (92%) of the title compound as a white solid.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. washeluted with MeOH/CH2Cl2 which

Sources & evidence

ORD record
ord-f8aa9d74c4da413eb4f9bb755bf7824a
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

Loading…