Acetamide → N-Acetyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cycloheptyl-acetamide

HRID 1975722Notes

Reaction equation

HRID 1975722 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH:23]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:20](O)=[O:21])=[CH:15][CH:14]=1.C(N(CC)CC)C.S(Cl)(C)(=O)=O.[C:42]([NH2:45])(=[O:44])[CH3:43].CN(C1C=CC=CN=1)C>C1COCC1>[C:42]([NH:45][C:20](=[O:21])[CH:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:14][CH:15]=1)[CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)(=[O:44])[CH3:43]

Participants

7

Reactant 5

HCID 178AcetamideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 113267232-Cycloheptyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-acetic acid

Product 1

HCID 9824020N-Acetyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cycloheptyl-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

8.0 g (0.02 mol) of 2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cycloheptyl-acetic acid and 4.0 g (5.6 ml/0.04 mol) of triethylamine are dissolved in 80 ml of THF, the solution is cooled to 0° C., and 2.3 g (1.6 ml/0.02 mol) of mesyl chloride are added. 2.4 g (0.04 mol) of acetamide and 7.2 g (0.06 mol) of dimethylaminopyridine (DMAP), dissolved in 20 ml of THF, are added at 0° C. The mixture is allowed to react at room temperature for 48 hours (stirring) and is then concentrated to dryness in vacuo, and the residue is extracted by stirring with 50 ml of water and 50 ml of dichloromethane. The organic phase is separated off, dried and concentrated to a small volume, and the residue is separated by column chromatography (silica gel 60, mobile phase: toluene/ethyl acetate/ glacial acetic acid=8/1/1).

Workup

  1. additionare added at 0° C
  2. customto react at room temperature for 48 hours
  3. concentrationis then concentrated to dryness in vacuo
  4. extractionthe residue is extracted
  5. stirringby stirring with 50 ml of water and 50 ml of dichloromethane
  6. customThe organic phase is separated off
  7. customdried
  8. concentrationconcentrated to a small volume
  9. customthe residue is separated by column chromatography (silica gel 60, mobile phase: toluene/ethyl acetate/ glacial acetic acid=8/1/1)

Sources & evidence

ORD record
ord-f1fa6553909348bd96d6ab4e36286eae
Source dataset
uspto-grants-1994_02
Patent number
US05288733

Reaction notes

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