N-Methylethylamine → HCID 178464486, compound

HRID 2047488Notes

Reaction equation

HRID 2047488 reaction equation
[N+](C1C=CC([N:10]([C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([N:22]3[CH2:26][C@@H:25]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[C@H:24]([N:34]([C:36](=[O:53])[N:37]([C:39]4[CH:44]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:42]=[C:41]([C:49]([F:52])([F:51])[F:50])[CH:40]=4)[CH3:38])[CH3:35])[CH2:23]3)=[O:21])[CH2:16][CH2:15]2)[C:11](=O)[O-:12])=CC=1)([O-])=O.[CH3:54][NH:55][CH2:56][CH3:57]>C(#N)C.C(OCC)(=O)C>[F:48][C:45]([F:46])([F:47])[C:43]1[CH:44]=[C:39]([N:37]([CH3:38])[C:36]([N:34]([C@H:24]2[C@H:25]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH2:26][N:22]([C:20]([C@H:17]3[CH2:16][CH2:15][C@H:14]([NH:10][C:11](=[O:12])[N:55]([CH2:56][CH3:57])[CH3:54])[CH2:19][CH2:18]3)=[O:21])[CH2:23]2)[CH3:35])=[O:53])[CH:40]=[C:41]([C:49]([F:50])([F:51])[F:52])[CH:42]=1

Participants

5

Reactant 2

HCID 12219N-MethylethylamineHCID 178485932HCID 178485932, compound

Product 1

HCID 178464486HCID 178464486, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound (0.20 g) obtained in Example 261 and N-methylethanamine (0.11 mL) in acetonitrile (2.7 mL) was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution, saturated aqueous ammonium chloride solution and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 80→100% ethyl acetate/hexane) to give the title compound (0.15 g, 83%) as a white powder.

Workup

  1. washwashed with water, saturated aqueous sodium hydrogen carbonate solution, saturated aqueous ammonium chloride solution and saturated brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (solvent gradient; 80→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-53aa8b6c68df40a6a5fc305aebf28fdd
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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