Dimethylamine → N,N-dimethyl-5-[(4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]-2-pyridinamine

HRID 43427Notes

Reaction equation

HRID 43427 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH3:29][NH:30][CH3:31]>CCOC(C)=O>[CH3:29][N:30]([CH3:31])[C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[O:9])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 244008621-[(6-Chloro-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

Product 1

HCID 35698205N,N-dimethyl-5-[(4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]-2-pyridinamineYield 55.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-[(6-chloro-3-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Example 51) (300 mg, 0.692 mmol) and dimethylamine (2M, 0.35 ml, 6.921 mmol) was irradiated to 100° C. for 3 h. The mixture was concentrated under vacuum, re-dissolved in DCM (20 ml), washed with water (3×10 ml), dried (Na2SO4) and concentrated under vacuum to leave the crude product. Flash chromatography (silica; 50% EtOAc in pet. ether) gave the title compound as a solid (169 mg).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionre-dissolved in DCM (20 ml)
  3. washwashed with water (3×10 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customto leave the crude product

Sources & evidence

ORD record
ord-dafd136fe60b4fb1bca2484903b83904
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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