Dimethyl Sulfoxide → HCID 131732941, compound

HRID 2171278Notes

Reaction equation

HRID 2171278 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.[C:23]([N:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH:28]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:27]1)(=[O:25])[CH3:24]>C(OCC)(=O)C>[C:23]([N:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:15]2[C:14]([F:18])=[CH:13][C:10]([C:11]#[N:12])=[C:9]([Cl:8])[N:16]=2)[CH:28]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:27]1)(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 73155326HCID 73155326, compound

Product 1

HCID 131732941HCID 131732941, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.096 ml) and 2,6-dichloro-5-fluoronicotinonitrile (109 mg) were added to a DMSO (2 ml) solution containing tert-butyl (1-acetyl-4-aminopiperidin-3-yl)carbamate (147 mg) obtained in the 4th step, followed by stirring at room temperature for 1 hour. Ethyl acetate was added to the reaction solution. The reaction solution was washed with water and saturated saline and dried over anhydrous sodium sulfate. Next, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:3). A light yellow solid of tert-butyl (1-acetyl-4-((6-chloro-5-cyano-3-fluoropyridin-2-yl)amino)piperidin-3-yl)carbamate (91 mg) was thus obtained.

Workup

  1. customobtained in the 4th step
  2. washThe reaction solution was washed with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationNext, the solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:3)

Sources & evidence

ORD record
ord-0698052ea95147d7a38cd3a05476d55d
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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