Diisopropylethylamine → HCID 86706872, compound

HRID 717893Notes

Reaction equation

HRID 717893 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:19][NH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C>CS(C)=O.CCOC(C)=O>[C:30]([O:29][C:27]([N:24]1[CH2:23][CH2:22][CH:21]([N:20]([CH3:19])[C:2]2[CH:3]=[C:4]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:26][CH2:25]1)=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateHCID 86666515HCID 86666515, compound

Product 1

HCID 86706872HCID 86706872, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 2-chloro-6-(trifluoromethyl)isonicotinate (0.47 g, 1.7 mmol, from Example 21, Step 1), tert-butyl 4-(methylamino)piperidine-1-carboxylate (0.54 g, 2.5 mmol, from Step 1) and N,N-diisopropylethylamine (0.58 mL, 3.4 mmol) in dimethyl sulfoxide (1.4 mL) was heated in an oil bath held at 100° C. for 26 hours. The mixture was cooled to room temperature and diluted with EtOAc. The organic solution was washed with three portions of water, one portion of brine, was dried over sodium sulfate, filtered and concentrated. Flash chromatography using a 40 g silica gel cartridge and eluting with a gradient from 0-20% EtOAc in hexanes afforded product as a white solid (0.30 g, 39%).

Workup

  1. temperaturewas heated in an oil bath
  2. washThe organic solution was washed with three portions of water, one portion of brine
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluting with a gradient from 0-20% EtOAc in hexanes afforded product as a white solid (0.30 g, 39%)

Sources & evidence

ORD record
ord-6775ec4d9a9749948970157ea2d8f8fd
Source dataset
uspto-grants-2015_11
Patent number
US09193733B2

Reaction notes

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