Acrylamide → 7-[(3RS,5SR)-4-(3-Amino-3-oxopropyl)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-N-[2-methyl-4-(trifluoromethoxy)benzyl]-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinoline-3-carboxamide

HRID 251864Notes

Reaction equation

HRID 251864 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([O:19][CH3:20])=[C:17]3[C:12]([C:13](=[O:42])[C:14]([C:26]([NH:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][C:31]=4[CH3:41])=[O:27])=[CH:15][N:16]3[CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:11][C:10]=2[F:43])[CH2:3]1.[C:44]([NH2:48])(=[O:47])[CH:45]=[CH2:46].Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C.CS(C)=O>[NH2:48][C:44](=[O:47])[CH2:45][CH2:46][N:7]1[CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([O:19][CH3:20])=[C:17]3[C:12]([C:13](=[O:42])[C:14]([C:26]([NH:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:38])[F:39])=[CH:32][C:31]=4[CH3:41])=[O:27])=[CH:15][N:16]3[CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:11][C:10]=2[F:43])[CH2:3][CH:2]1[CH3:1]

Participants

6

Reactant 3

HCID 6579AcrylamideHCID 23665649Lithium perchlorateHCID 724938447-[(3RS,5SR)-3,5-Dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-N-[2-methyl-4-(trifluoromethoxy)benzyl]-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 724938167-[(3RS,5SR)-4-(3-Amino-3-oxopropyl)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-N-[2-methyl-4-(trifluoromethoxy)benzyl]-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinoline-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A few drops of acetonitrile are added at room temperature to 55 mg of the compound of Example 52, 18 mg of acrylamide and 35 mg of lithium perchlorate, so that a stirrable suspension results. The mixture is heated to 70° C. over night and left to cool. After the addition of DMSO the whole mixture is separated by preparative HPLC (Method 5). After concentrating the suitable fractions and drying under high vacuum 30 mg (40% of theory) of the title compound are obtained.

Workup

  1. customresults
  2. waitleft
  3. temperatureto cool
  4. customis separated by preparative HPLC (Method 5)
  5. concentrationAfter concentrating the suitable fractions
  6. dry with materialdrying under high vacuum 30 mg (40% of theory) of the title compound
  7. customare obtained

Sources & evidence

ORD record
ord-0b93aa94662c4e62b1e0a9feeacf9e77
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Reaction notes

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