Pyridine → HCID 23521690, compound

HRID 392441Notes

Reaction equation

HRID 392441 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([NH:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:11]=[CH:12][C:13]=1[Cl:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:29][C:30]([F:37])([F:36])[CH2:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH2:1]([C:8]1[CH:9]=[C:10]([N:15]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[S:32]([CH2:31][C:30]([F:37])([F:36])[F:29])(=[O:34])=[O:33])[CH:11]=[CH:12][C:13]=1[Cl:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 69880080HCID 69880080, compound

Product 1

HCID 23521690HCID 23521690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3-benzyl-4-chlorophenyl)pyrid-3-ylmethylamine (0.04 g, 0.13 mmol)and pyridine (1 ml) was dissolved in DCM. The reaction was cooled in an ice-bath to which was added dropwise 2,2,2-trifluoroethylsulfonyl chloride (0.59 g, 0.32 mmol). The mixture was stirred at room temperature overnight. After evaporation of solvent, the residue was dissolved in EtOAc and washed with cold NaHCO3 and brine, and evaporated to dryness. Chromatography gave the title compound. 1H NMR: 8.51 (d,1H,J=3.9 Hz), 8.27 (s,1H), 7.59 (d,1H,J=7.8 Hz), 7.34 (t,1H,J=8.3 Hz), 7.28 (d,2H,J=7.8 Hz), 7.21 (m,2H), 8.03 (m,3H), 6.89 (d,1H,J=2.4 Hz), 4.78 (s,2H), 4.01 (s,2H), 3.73 (q,2H,J=9.3 Hz). MS calcd 454.1; MS (M+1) 455.0.

Workup

  1. temperatureThe reaction was cooled in an ice-bath to which
  2. customAfter evaporation of solvent
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with cold NaHCO3 and brine
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5cdf84ee9a9a48fb80cbe9cbcdbe1759
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

Loading…