Dimethyl Sulfoxide → HCID 117643702, compound

HRID 2171279Notes

Reaction equation

HRID 2171279 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[N:16]=[C:15](Cl)[C:14]([F:18])=[CH:13][C:10]=1[C:11]#[N:12].CS(C)=O.[NH2:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:26][CH:25]1[NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>O.C(OCC)(=O)C>[C:44]([O:43][C:41]([NH:40][CH:25]1[CH:24]([NH:23][C:15]2[C:14]([F:18])=[CH:13][C:10]([C:11]#[N:12])=[C:9]([Cl:8])[N:16]=2)[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:26]1)=[O:42])([CH3:47])([CH3:45])[CH3:46]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 117643532HCID 117643532, compound

Product 1

HCID 117643702HCID 117643702, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.22 ml) and 2,6-dichloro-5-fluoronicotinonitrile (470 mg) were added to a DMSO (2.4 ml) solution containing benzyl 4-amino-3-((tert-butoxycarbonyl)amino)piperidin-1-carboxylate (470 mg) obtained in the 2nd step, followed by stirring at room temperature for 0.5 hours. Ethyl acetate and water were added to the reaction solution for extraction. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 15:3) and a white solid of benzyl 3-((tert-butoxycarbonyl)amino)-4-((6-chloro-5-cyano-3-fluoropyridin-2-yl)amino)piperidin-1-carboxylate (500 mg) was thus obtained.

Workup

  1. customobtained in the 2nd step
  2. washThe organic layers were washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 15:3)

Sources & evidence

ORD record
ord-f04d3ed445284133bed051c704ad8754
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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