Diisopropylethylamine → HCID 86706866, compound

HRID 717886Notes

Reaction equation

HRID 717886 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].[NH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.C(N(CC)C(C)C)(C)C>CS(C)=O.CCOC(C)=O>[C:29]([O:28][C:26]([N:23]1[CH2:24][CH2:25][CH:20]([NH: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])[CH2:21][CH2:22]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 86666515HCID 86666515, compound

Product 1

HCID 86706866HCID 86706866, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 2-chloro-6-(trifluoromethyl)isonicotinate (3.0 g, 11 mmol, Example 21, Step 1), tert-butyl 4-aminopiperidine-1-carboxylate (4.3 g, 21 mmol, Aldrich) and N,N-diisopropylethylamine (3.7 mL, 21 mmol) in dimethyl sulfoxide (9.2 mL) was heated to 100° C. for 20 hours. The mixture was cooled to room temperature and diluted with EtOAc. The combined organic extracts were washed with water (3 times) and brine, dried over sodium sulfate, filtered and concentrated. Flash chromatography using a 120 g silica gel cartridge and eluting with a gradient from 0-15% EtOAc in hexanes afforded product as a white solid (3.4 g, 72%). LCMS (M+Na)+: 468.2.

Workup

  1. washThe combined organic extracts were washed with water (3 times) and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with a gradient from 0-15% EtOAc in hexanes afforded product as a white solid (3.4 g, 72%)

Sources & evidence

ORD record
ord-ef954e517a3b489aad73b015f4796934
Source dataset
uspto-grants-2015_11
Patent number
US09193733B2

Reaction notes

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